Community Events

This May: All 4 weekends!

1st Weekend

Friday

✨First Fridays @ Leonardtown Square

 Many businesses will have specials going on as well as live music on the square 6-8PM, and an all-ages art project in the alley 6-8PM.

FREE


Friday - Sunday

✨Spring Festival @ St. Mary’s Fairgrounds

A weekend of family fun with entertainment, food, yard sale, artists, crafters, kid's games and much more!

5-10PM (Fri) 10AM-10PM (Sat) 10AM - 6PM (Sun) |$6/Adult, $3/ Kids 6-12, FREE 5&Under


Saturday

✨May Day @ Historic St. Mary’s City

To commemorate the season, this event honors the tradition of playing games from the 17th century and taking part in hands-on nature activities.

10AM - 4PM | $10/Adult, $6/Kids, FREE 5&Under


2nd Weekend

Saturday

✨Spring Shine Festival @ Southern Trail Distillery 

Sip on a specialty cocktail, indulge in regional snacks & cuisine, peruse the stalls of local artisans and vendors, and listen to live music.

10AM - 5PM| FREE event admission 


✨Mother’s Day Market @ Annmarie Gardens

A morning of browsing through a delightful selection of vendors offering all things handmade, homemade, and homegrown. Moms will enjoy all the booths - and you'll find gifts for the mothers in your life!

9AM - 12PM | FREE admission to market area


3rd Weekend

Saturday

✨National Pick Strawberries Day @ Lyon Family Farm

Bounce house, face paint, food trucks & treats in addition to your strawberry picking! 

10AM - 5PM | FREE event admission


✨Military Appreciation Concert @ Leonardtown Wharf

Cover Your Six Band will play for the On the Water's Edge Concert Series. Come by water or land - Bring your lawn chair or blanket and enjoy live music. Wine and ice cream vendors will be there too!

5-7PM | FREE 


4th Weekend

Friday & Saturday

✨Leonardtown Trolley @ Leonardtown Neighborhoods & Square

Save on gas and ride the trolley around Town to enjoy the specialty shops, fine dining, exciting activities and fun! 

5-10PM | FREE


Saturday

✨RenFest Southern Maryland @ Brüdergarten and Viking Axe Throwing

Enjoy entertainment, food and drink, artisan vendors, demonstrations, kids' activities and so much more at this Medieval, Viking, and Renaissance life festival.

10AM - 8PM | FREE

This April: All 4 weekends!

1st Weekend

Saturday

✨Cherry Blossom Festival @ Lexington Manor Passive Park

Stroll through the park and enjoy the bright blossoms of spring! Enjoy loads of additional activities including disc golf, arts & crafts, golf demos, food & retail vendors, live music.

12-4PM | FREE


Saturday & Sunday

✨Southern Maryland Fishing & Outdoor Adventure Fair @ St. Mary's County Fairgrounds

Fishing and outdoor enthusiasts can learn from local captains at various seminars and browse vendors for all your gear needs. Kids can enjoy a casting contest and adults can enter for door prizes. 

8AM  -3PM |$5/Ticket, FREE Kids 12&under


2nd Weekend

Saturday

✨First Landing Wine & Arts Festival @ St. Clement’s Island Museum 

Enjoy wine from exclusively St. Mary's County wineries while browsing local crafted items and more on museum grounds along the scenic shores. Several food vendors will also be available as well as kids’ and family activities.

10AM - 5PM| FREE event admission 


✨Battle by the Bay Truck & Tractor Pull @ St. Mary's County Fairgrounds

This classic SOMD event is sure to be a dirt-flying, rolling smoke-filled, high-horsepower, adrenaline-packed good time! 

Gates open 3PM, Pull begins 5pm | Adults/$20, Ages 5-12/$10, FREE Kids 5&under


3rd Weekend

Saturday

✨Earth Day @ Summerseat Farm

Learn how you can help keep our planet beautiful from exhibits and demonstrations by environmental groups, say hello to the beautiful farm animals, shop handcrafted products from local vendors, enjoy live music, and grab a bite to eat at one of the food trucks. 

11AM - 4PM | FREE event admission


Sunday

✨Fairy & Gnome Home Festival @ Annmarie Garden

Dress up in your favorite fantasy finery and join us for the most magical day of the year! Explore the Wondrous Woods, shop the enchanted marketplace, search for over 180 fairy houses, meet whimsical characters and wandering performers, make enchanting arts and crafts, engage in imaginative play, enjoy nature explorations, adorable animal encounters, unicorn rides, and more. Food and drink will be available.

11AM- 4PM| $10/person online, FREE Kids 2&under 


4th Weekend

Saturday

✨Spring Fling Car Show @ Leonardtown Square

St. Mary's Rod & Classic Car Club presents a great day of admiring hot rods, vintage cars, and antique vehicles. There will be a selection of food and drinks, music, door prizes, a 50/50 raffle, and shopping.

8AM - 4PM | $5 spectator fee; proceeds benefit Hospice of St. Mary's

This March: All 5 weekends!

1st Weekend

Friday

✨March Madness First Friday @ Town of Leonardtown

Explore, dine, and shop your way to a great Friday night! You'll find extra fun and special deals all around town.

All Day | FREE 


Saturday

✨COSMIC Symphony Orchestra Concert @ St. Mary’s College 

Our local Symphony’s FREE concert titled Rebirth will feature the winners of the 2023-24 Young Artists Competition and the music of Ludwig van Beethoven.

3- 5PM | FREE 5&under

 

✨Annmarie After Hours @ Annemarie Garden

An after-hours gathering in celebration of a new exhibit featuring incredible art, live music, a food truck, cash bar.

5-7PM| $5/Ticket for non-members | Adult Only 


2nd Weekend

Saturday

✨Easter Joy! Family Event @ Lexington Park United Methodist

This family-friendly program will feature crafts, Bible stories, and an age-based egg hunt.

2- 4PM | FREE | Registration encouraged


✨STEAM DAY @  Patuxent River Naval Air Museum

A great opportunity for students to explore the world of science, technology, engineering, art, & mathematics with many exhibitors, hands-on activities for all ages to enjoy! 

10AM - 3PM | FREE for kids with adult ticket purchased


3rd Weekend

Saturday

✨St. Patrick's Day Leprechaun Hunt @ American Chestnut Land Trust 

Based on the book, “The Leprechaun Story,” families go through a “field of shoes” reading clues to help them find the pot of gold. Bonus: Find rocks hand painted with 4-leaf clovers.

10AM - 3PM | $5/ Family Suggest Donation


✨ Shamrock Showdown of Calvert Co. @ Johnson Springs Estates

A lucky family day of activities: live music, bounce house, axe throwing, breweries, distilleries, food trucks, & local artisans. Pet friendly too! 

11AM - 4PM | FREE to enter


4th Weekend

Saturday

✨41st Annual Easter Egg Festival @ St. Mary's County Fairgrounds,

Don’t miss this Southern Maryland spring staple, featuring the Easter Bunny and Mrs. Cottontail, egg hunts, live entertainment, free arts & crafts, face painting, delicious local food & shopping!

11:30am - 4PM | $5/Ticket 


Sunday

✨Easter Egg Hunt @ Hallowing Point Park

Join Calvert Co. Parks&Rec for the annual hunt including photos with the Easter Bunny, music, inflatable attractions, merchandise vendors, food trucks and face painting.

12:30 - 3PM | FREE 


5th Weekend

Saturday

✨D&D Saturdays @ Charlotte Hall Library 

Dungeons And Dragons for players of all experience levels. Characters will be provided for players in this month's game. Drinks and snacks will be provided.No experience required!

2- 4PM | FREE | Ages 16+, or adult with 16 &under


✨Pics with Easter Bunny @ Earthwise Pets 

Stop in to take fun pictures with the Easter Bunny anytime, pets or kids! 

11AM -2PM | FREE

This February: All 4 weekends!

1st Weekend

Friday

✨First Fridays @ Leonardtown Square

Come for a fun day of shopping, dining & exploring with specials throughout town at participating businesses.

All Day | FREE 


Friday-Sunday

✨”Photographs Along the Underground Railroad" @ St. Clement's Island Museum

The traveling national exhibit, Through Darkness to Light: Photographs Along the Underground Railroad, will be on display and running through Black History Month. 

10AM - 5PM | $3/Adult, $1.50 Ages 6-18 | FREE 5&under

 

2nd Weekend

Saturday

✨Valentine Market @ Annemarie Garden

Indoor and Outdoor vendors will have homemade, handmade, or homegrown products gifts for all the sweeties in your life! 

9AM -2PM | FREE to enter market area


✨My Furry Valentine @ Earthwise Pets

Celebrate Valentine's Day with your Furry Valentine by taking pictures with Pup Cupid. Pet Adoptions happening too!

11- 2PM | FREE


✨Sweetheart Dance @ Ridge Volunteer Fire Department Auxiliary

Dust off your dancing shoes and take your prince and/or princess out for a fun afternoon with DJ, desserts & punch, and photo props!

4 -6PM | $10/Couple or $20/Family


3rd Weekend

Friday-Sunday

✨A Night on Broadway: A Journey Through Love @ Three Notch Theatre

A dazzling cabaret show from The Newtowne Players that takes audiences on a romantic journey through the enchanting world of Broadway.

8 - 10PM (Fri & Sat) 3-5PM (Sun) | $20/Adult, $15/Child


4th Weekend

Saturday

✨TEDxGreat Mills @ Three Notch Theatre

Join us for a lively evening of talks, performances, and interactive conversations with 6 fabulous speakers and what happens when we open our minds to infinite possibilities.

7 - 9:30PM | $25/Ticket 


✨The Princess Concert @ Nancy R. and Norton T. Dodge Performing Arts Center

An evening of songs from your favorite royals, heroes and villains of stage and screen! 

7 - 9PM | $10/ticket, FREE 5&under

This January: Last 3 weekends!

2nd Weekend

Friday

✨Trivia Night @ Corteau Vineyards

Bring your A game for trivia! Prizes for 1st & 2nd place!

4-6PM | FREE | Maximum group size of 6 people 


Saturday - Monday

✨”Shaping the Dream” Clay Event @ Annmarie Garden

Drop in for an uplifting community art event where you can sculpt with air-dry clay and view an exhibit inspired by the life of Dr. Martin Luther King, Jr. 

11AM - 4PM | FREE: limited tables available | All ages and abilities 


3rd Weekend

Saturday

✨Farmers Market @ Home Grown Farm Market

Shop all things whether goods and food, it will all be local! Food trucks on site.

10AM - 1PM | FREE


Sunday

✨Jam-uary: Open Acoustic Jams @ Bay Fibers Studio

Whether a novice or veteran singer or instrumentist, come share your talents for a laid back, open acoustic jams of folk, bluegrass, oldtime, classics, etc.

10:30am-noonish | FREE


4th Weekend

Saturday

✨Appraiser Fair @ St. Clement's Island Museum

Visit with expert appraisers as they determine the value of your prized possessions. Appraisers for dolls, furniture, glassware, pottery, artwork, music boxes, and coins will be available.

10AM - 3PM | FREE 


✨Live Boxing @ The Rex Theatre

Great fights in the ring and awesome food and drinks outside the ring! 

Doors open 1PM | $35/General Admission

This December: First 4 weekends!

1st Weekend

Friday

✨The Polar Express @ Leonardtown Town Market

Watch this classic Holiday movie with the whole family! Bring your chairs and bundle up.

6:30PM | FREE


Friday - Sunday

✨Annmarie Garden In Lights @ Annmarie Garden

Walk around and gaze upon the hundreds of light displays! Enjoy a beautiful miniature train display. Shop for gifts, and enjoy hot cocoa and local food vendors. Get a family photo with Santa (Sun. only)

5 - 9PM | Advanced Tickets Required | $15/Person, FREE 2& under


2nd Weekend

Friday & Saturday

✨Christmas Fun @ Flat Iron Farms

A magical night with light displays, pony rides, pictures with Santa, a petting zoo, food and gift vendors, and so much more!

5 - 9PM | FREE


Saturday

✨Solomons Christmas Walk @ Calvert Marine Musuem 

Enjoy musical entertainment, visit Santa and the Otter mascot, and make holiday crafts. Santa's Coffee House will be open with complimentary hot cocoa, coffee, and holiday cookies. Also catch the Lighted Boat Parade from 6:30-7:15PM down by the Solomon Boardwalk.

6 - 9PM | FREE


3rd Weekend

Friday & Saturday

✨Ballet Caliente's NUTCRACKER @ SMC Performing Arts Center

Step into the enchanting world of The Nutcracker live ballet, a timeless holiday classic that has captured the hearts of audiences for generations. 

6:30PM Fri&Sat 1PM Sat | $25/ Ticket, FREE 2& under 


Saturday

✨Gingerbread House Decorating Contest @ Leonardtown Town Market

Come check out decked out homemade Gingerbread Houses on display and see who wins at 2PM!

9AM - 3PM | FREE


Sunday

✨Visit with The Grinch @ Ruddy Duck

Bring your camera and littles to snap a picture with the Grinch. Crafts & candy canes will be handed out to each child. 

          2 - 4PM | FREE


4th Weekend

Friday & Saturday

✨Christmas Doll & Train Exhibit @ St. Clement's Island Museum

Families can enjoy a holiday exhibit of antique and collectible dolls like Barbie and American Girl, classic trains, and other vintage toys in this festive holiday display.

10AM - 5PM | $3/Adults, $1.50/Children, FREE 5& under


✨Holiday Exhibit @ Piney Point Lighthouse Museum

Come enjoy guided tours for all ages of the lighthouse and museum. The museum will be decorated for the holidays and special festive exhibits will be available.

10am-5pm | $7/Adults, $3.50/Students, FREE 5& under

This Weekend: November 3rd, 4th, and 5th

Weekend Events


It’s officially jacket and hat season, get bundled up and enjoy the crisp air and these weekend events!


Friday

✨ First Fridays @ Leonardtown Square

Wonderfully walkable historic downtown Leonardtown is always teeming with activity, but on First Friday, the businesses turn it up to eleven!

FREE


✨Yoga S'more Fun@ Xella Winery

Join SPICE Studio for a 60 minute yoga class, a smore treat, mulled wine& time by the fire.

5 - 7:30PM | $40/person


Saturday

✨Community Carnival @ Kings Christian Academy 

There will be a variety of 35+ carnival games and attractions, featuring laser tag, a rockwall, zip line, pony rides, and a Ninja Warrior Course!

2 - 6PM | FREE


✨Artisan & Vendor Market @ Summerseat Farm

Enjoy the beautiful surroundings of this working farm as you browse handcrafted and vintage decor, gifts, and clothes, and more from local artisans and vendors. 

9AM - 3PM | FREE


✨Coastal Arts Holiday Market @ Ltown Wharf 

Enjoy the day browsing the work of local artists and crafters and get ahead of holiday shopping.

9AM - 3PM | FREE


✨American Indian Heritage Day @ Jefferson Patterson Park and Museum

Celebrate 10,000 years of history and culture with activities, educational demonstrations, native dancers and more!

11AM - 4PM | FREE


✨Jellyfish Day @ Calvert Marine Museum

Stop by to check out the Moon jellyfish exhibit and discover fun facts about the bay’s other jellyfish species through activities in the River to Bay Gallery!

11AM - 4PM | $11/Adult, $6/Ages 5-12, FREE Ages 4 & under


✨Sip n Search @ Spider Hall Farm

Beverage sampling stations will be throughout the corn maze. Then take a hayride down on the farm and enjoy a DJ and cornhole too! Food and beverages available to purchase. 

6 - 10PM | $12/Ticket (must buy online before) | 21+

This Weekend: October 27th, 28th, and 29th

Weekend Events


Costumes, candy, and more candy await you this weekend with plenty of spooky events! 


Friday

✨ Bad Art Night @ Annmarie Garden

Pumpkins are the inspiration for this adults-only evening of crazy crafting! Enjoy popcorn and other Halloween treats, along with music and cash bar! 

4:30 - 6:30PM | $7/person; Members Free | 21+ 


Friday & Saturday

✨The Haunting at Piney Point @ Piney Point Lighthouse Museum

This self-guided Halloween-themed walking tour is free to the public and appropriate for all ages. 

5 - 9PM | FREE


Saturday

✨BBQ at the Barn @ Sassafras Farm

Bring the family for a good time at the Barn with live music and vendors while there is a BBQ competition. Food trucks and a local brewery will be available. 

12 - 7PM | FREE


✨Hide Tanning Workshop @ Historic St. Mary’s City

Workshop for beginners and offers a hands-on experience to learn the basics on how to turn skins of deer into usable materials. 

9:30AM – 4PM | $25 /NonMembers $20/Members Registration required | Ages 14 & up


✨Halloween on the Square @ St. Mary’s Square 

Get ready for a fun afternoon filled with costumes, eerie entertainment, and Professional Wrestling!

4PM | FREE


Saturday & Sunday

✨COSMIC Symphony Concert @ Various Locations

An exciting season opener concert; A COSMIC Homecoming featuring St. Mary’s County native & COSMIC alum Julia Henderson, who now performs as a professional cellist in NYC!

3 - 5PM St. Mary’s College of Maryland (Sat) Huntingtown High School (Sun) | FREE


✨Straw Bale Maze @ Ltown Town Market

Make your way out of the maze to pick your pumpkin. There will be cookie decorating, face painting, games and food trucks on site!

10AM - 5PM (Sat) 10AM - 5PM (Sun)| $10/person, 2 & under FREE


Sunday

✨Trunk or Treat @ Real Life Church

Wear costumes for this family-friendly event with tons of trunks, fun, and oh--yeah--lots of candy! 

6 - 8PM | FREE

This Weekend: October 13th, 14th, and 15th

Weekend Events


Whether you want to create art, browse and enjoy art, or buy it…there are awesome options this weekend!


Friday

Plein Air @ Leonardtown Wharf 

Enjoy an evening of painting beautiful Breton Bay. Bring your supplies for open paint for the Plein Air class taught by a professional artist. 

4:30 - 7:30PM | FREE


✨ After Hours @ Annmarie Garden

Enjoy live music, tour the new exhibit, and appreciate an evening of art and nature. You’ll find a cash bar and food trucks as well!

5 - 7PM | $5/person; Members Free


Friday & Saturday

✨Fall Art Show @ Southern Maryland Sailing Association

Come to Solomons for lunch and to shop for early holiday gifts at reasonable prices. All work is by local artists.

Sat 10AM – 6PM, Sun 11AM – 5PM | FREE


Saturday

✨Leonardtown Summer Music Festival Finale @ Leonardtown Square

Don't miss the season finale of the Leonardtown Summer Music Festival! Vertigo Red, Maryland's premiere rock cover band,

7 - 10PM | FREE


✨Coastal Arts Market @ Ltown Wharf

Shop local hand-crafted goods at this magnificent monthly seasonal market where everything is homegrown or home-made.

9AM - 3PM | FREE


✨LexiCon @ Lexington Park Library

Join lovers of comic books and fantasy for trivia, an obstacle course for kids, a cosplay contest, a streamer panel, and prizes!

12 - 4PM | FREE


✨Spirits & Steeds Fall Festival @  Freedom Hill Horse Rescue 

Sip and savor tastings, enjoy an Irish Dance performance, shop, eat from available food trucks, meet some horses, and enjoy fun for the whole family.

1 - 6PM | $25/person , 15 & Under FREE *Ticket sale ends Fri. night


Sunday

✨Concert at Linden @ Calvert Co. Historical Society

Bring your lawn chairs and coolers as you listen to Riverside South band.

3 - 5PM | FREE

This Weekend: October 6th, 7th, and 8th

Weekend Events

Local and foreign traditions and cultures can be embraced whether through food, drink, or activities this weekend!


Friday

Leonardtown Square Bar Crawl @ Various Restaurants along Ltown Square 

During the bar crawl, you can get a passport stamped at various locations for an opportunity for YOU to win limited edition Fall Bar Crawl merchandise. 

11AM - Midnight 


✨Octoberfest First Friday @ Ltown Square

Enjoy an interactive mural art activity, face painting, balloon art , and live music around the square.

5 - 9PM | FREE


Adventures in Raptor Research @ Flag Ponds Nature Park

Learn about what is being done to study and help save raptors, including the current research project in Calvert County to monitor the raptor populations and how you can help!

7 - 9PM | Older teens and up | FREE


Saturday

✨Wild Edibles Walk @ American Chestnut Land Trust

Learn how to identify and harvest edible plants and mushrooms as well as avoiding the poisonous look-alikes in this walk and talk. 

2 - 4PM | FREE


✨Monster Market @ Annmarie Garden

Indulge into the love of autumn and the utterly monstrous with this over-the-top market featuring lots of treats inspired by the season.

9AM - 2PM | FREE to enter the market


✨Fall Market @ Southern Trail Distillery 

Enjoy cocktails, local vendors/food trucks & awesome music while relaxing on the grassy knoll. 

10AM - 5PM | FREE to enter the market


✨Brüderfest @ Brüdergarten Beer Garden

Take in the fun and excitement of German tradition with German beers + spirits, delicious light fare foods, live dancing, and dog contests!

11AM - 7PM (family friendly), after 7PM (21+) | $5/ Person; 10 & under FREE


Saturday & Sunday

✨Southern Maryland Heritage Festival @ Historic Sotterley

Experience the unique heritage and history of SOMD featuring skilled artisans, cultural foods, a variety of spirits, live music, demonstrations, and children's activities. 

12 - 5PM | $25 in advance, $30 at the gate/Adult, Ages 13-17/$10, 12 & under FREE


Sunday

✨Tractor Parade @ Leonardtown Square

Generations of antique power equipment - from farm tractors to unique trucks - line the streets of Ltown.

1 - 3PM | FREE

This Weekend: September 29th, 30th, and October 1st

Weekend Events

Many opportunities to not eat corn, but to maze through it! Plus all things comics and local food!


All Weekend

Opening Weekend @ Forrest Hall Farm

The whole family can enjoy the play area and barn animals, the maze, a hayride and each paid admission gets a mini pumpkin.

9AM - 5PM | $10/Person, 3& under FREE


Harvest Festival @ Horsmon Farm

Family fun on the farm includes farm animals, pumpkin patch, hay rides, mazes, rubber duck races and much more.

$10/Adults, $12/Kids 2-12 with small pumpkin, 2& under FREE


Friday

Maze Craze in the Moonlight @ Rolling Acres Farm

Enjoy a night of adventure as you take on the corn maze at dark, make sure to bring a flashlight!

7 - 10PM | $12/Person or $10/Person with Family of 4 or more


Friday & Saturday

Leprechaun Lilly's Children's Consignment Sale @ St. Mary’s County Fairgrounds

One-stop-shop for everything baby to teen and mom too!

9AM - 8PM (Fri) 2PM (Sat)


Saturday

Southern Maryland Comic Con @ Capital Clubhouse

A celebration of comics, toys, TV, film, art, cosplay, games, and all things nerdy. 

10AM - 4PM | $12/Adult, $5/Ages 4-14


Blessing of the Fleet @ Historic St. Mary’s

Commemorating the time-honored tradition of blessing the Southern Maryland watermen's fleet of boats with family entertainment, local food, an evening concert, and fireworks!

12PM - 10PM | $10/Person, 10& under FREE


Taste of St. Mary’s @ Ltown Square

Sample specialties from local restaurants and caterers,  free entertainment, kid activities, and a classic car show.

1 - 4PM 


Saturday & Sunday

Corn Maze @ Bowles Farms

Find your way through 14 acres of corn, enjoy food, cupcakes, rides, a playground, and a pick-your-own pumpkin patch.

10AM - 6PM (Sat) 5PM (Sun) | $15/Person, 3& under FREE


Corn Maze Opening @ Jake’s Produce

Family fun includes food trucks, wagon rides, corn pits, pumpkins, corn mazes and much more.

9AM - 5PM | $15/Person, 2& under FREE


Sunday

Sip & Shop @ No Thyme to Cook

Local craftsmen and producers offer their wares at this artisan craft fair with seasonal food and drink.

11AM - 5PM | FREE to enter


Invasives Festival @ Jefferson Patterson Park

Come create your own baskets, straw mats, laundry detergent and much more, all from invasive plants and insects! 

11AM - 3PM | FREE

This Weekend: September 22nd, 23rd, and 24th

Weekend Events

Events this weekend include the 5 important F’s: Fall, Fair, Family, Fun and Fruit!


All Weekend

✨County Fair @ St. Mary's County Fairgrounds

This classic fair is filled with rides, games, food, vendors, music, animals, and so much more. 

9AM - 9PM (6PM on Sun)| Gate Fees: $10/Adult, $1/Ages 6-12, Under 6 FREE


✨ Harvest Festival Celebration @ Horsmon Farm

Family fun includes farm animals, pumpkin patch, hay rides, mazes, rubber duck races & much more! 

10AM (Fri) 11AM (Sat/Sun) - 5PM | $10/Adult, $12.00/Ages 2-12, Under 2 FREE


Saturday & Sunday

✨Fall Family Fun @ Jake’s Produce 

Corn Maze, bounce house, corn pits, slides, ball pits, and other fun awaits! 

9AM - 5PM | $15/Person, Under 2 FREE | Weather dependent, check out their Facebook


Saturday

✨RiverFest @ Historic St. Mary's City

Celebrate the St. Mary’s River with live music, exhibits and re-enactments like Militia Muster, kayaking, food and drinks. 

11AM - 4PM | FREE


✨Leonardtown Summer Music Festival Concert @ Port of Leonardtown Winery

 Enjoy the laid-back vibe as Unfinished Business performs popular rock and country hits while sampling award-winning wine.

3 - 6PM | FREE


✨Live Music @ Perigeaux Vineyards & Winery

Enjoy an afternoon at the vineyard featuring live music by Susan St. George!

2 - 6PM | FREE


Sunday

✨Pawpaw Party! @ Flag Ponds Nature Park

Discover Maryland's best kept secret fruit! Take a hike to learn about Pawpaws and taste some of the many ways you can enjoy them.

10AM - 12PM | $8/Non-members, Members FREE

This Weekend: September 15th, 16th, and 17th

Weekend Events

Coastal vibes all around this weekend, whether shopping, viewing a shark movie, or acting like a pirate! 


Friday

Kelly Bell Band @ St. Mary’s College

Enjoy this electrifying band, who has won two prestigious Maryland Music Awards!

7 - 9PM | SOLD OUT


✨Finding Nemo Screening @ LTown Alley

Bring your lawn chair or blanket and pack a picnic for an outdoor screening of Finding Nemo!

7PM | FREE 


Sunset Cruise @ LTown Wharf

Admire the stunning scenery of St. Mary's County from the water on a vintage charter boat.

5:15 - 7:15PM | $25/person | Ages 12& up


Saturday

Coastal Arts Market @ Leonardtown Wharf

All items are handcrafted by some of Southern Maryland's very talented craftsmen, artists, and makers.

 9AM - 3PM | FREE 


Pirate Day @ Calvert Marine Museum  

Throw on your best pirate outfit and head to the museum for crafts, songs, and other pirate activities! 

10AM - 3PM | Museum Admission: $11/Adult, $6/Ages 5-12


✨Jaws Screening @ Leonardtown Wharf

Bring your lawn chair or blanket and pack a picnic for an outdoor screening of Jaws!

7PM | FREE


✨ Hunters Bash @ Calvert County Fairgrounds

Auction with great items, games and more hosted by PFVFD & Ducks Unlimited! Over $20K in cash and prizes!

12 - 4:30 PM | $25-50+ Auction Tickets


✨Craft Beer Festival @ No Thyme to Cook 

 This celebration of the craft brewing industry will showcase a variety of ales, lagers, ciders, and meads.

11AM - 7PM | $25 Tickets with different time slots


Saturday & Sunday

Artsfest '23 - @ Annmarie Garden

Festival of visual and performing arts with 170+ artists booths, 40+ performers, activities for kids, great food, wine & beer

10AM - 5PM | $10/person online ticket, Kids 11 & under FREE


Sunday

AeroPark Fly-In Farmers Market @ SMC Regional Airport

Historic Sotterley is sponsoring this unique market full of local goods, meals, and craft beverages at the Airport Terminal, don’t worry you don’t need a plane!

 9AM - 1PM | FREE

This Weekend: September 8th, 9th, and 10th

Weekend Events

Tons of opportunities to learn something new and enjoy family fun this weekend throughout Southern Maryland by boat or land! 


All Wknd:

Opening Weekend @ Rolling Acres Farm 

Family Farm Fun including a corn maze, slides, petting zoo, food trucks, and much more.

10am-6pm | $12/person, 2&under FREE


Friday

Sunset Cruise @ Leonardtown Wharf

Relax and unwind on a vintage charter boat with your homemade picnic through Breton Bay.

5:30- 7:30 PM | $35 | Ages 12& up


Dueling Pianos @ Taphouse 1637

Rock it out with the dueling piano show like the good ole days.

8 PM


Saturday

RecoveryFest @ Annmarie Garden

Come celebrate those in recovery with free, family-friendly fun, including games, face-painting, inflatables, and hands-on learning!

10AM - 2PM | FREE


Indigenous Heritage Day @ Historic St. Mary's City

Celebrate and honor the lifeways of indigenous peoples. Learn skills, try crafts, watch demonstrations, and enjoy performances. 

10AM- 4PM | $6-9/person, 5&under FREE


Basket Weaving: Twining With Natural Materials @ Jefferson Patterson Park 

Learn how to make a small round basket from day lilies and iris foliage using the technique of twining.

10AM- 3PM | $25 | Ages 15& up


SLVFD Annual Bourbon & Seafood Festival @ St. Leonard Fire Department

Relax with some adult beverages available from our local distilleries, wineries and breweries along with your favorite seafood and enjoy some music at this family fun festival!

11AM- 6PM | $12


Sunday

Pet Funday Sunday 5K Fun Run/Walk @ North Beach Pavilion

Bring your well-mannered pets for a fun run walk for the Humane Society of Calvert County!

8:30 AM | $25-35


Sip and Save Beer Tasting @ American Chestnut Land Trust

Enjoy a beer-tasting from local/regional breweries at this annual event!

1-5PM | $20/person 


Dinner & Cruise Series @ St. Clements Museum

Step on the St. Clement's Island Water Taxi and enjoy the views while the water tour guide discusses World War II on the Potomac, then off to dinner!

4-8PM | Reservations required


This Weekend: September 1st, 2nd, and 3rd

Weekend Events

While it may be a ‘BER month and Pumpkin Spice Lattes are here, soak up the last of summer this weekend with some fireworks and other fun events.


Friday

✨First Fridays on Leonardtown Square: Live Music (4-7pm), Aerial Performance and Fire Dancing  (5-8 pm) 

FREE


Saturday

@ Leonardtown Wharf: 2nd Annual Sidewalk Art Contest (10am -5pm), Water’s Edge Concert (3-7:30 pm), Fireworks Spectacular Show (8pm) 

FREE


Fossil Field Experience @ Cove Point 9am-12pm 

Discover fossils and delve into their mysteries and the valuable insights they provide into history.

9am-12pm | Ages 8&up | $25


Open House @ Drayden African American Schoolhouse   

Enjoy history at one of the best-preserved African-American schools in the nation

11am-2pm | FREE


PyroJam @ Jefferson Patterson Park 

This festival for kids and adults features live music and an amazing International Fireworks Competition! 

3-10:30 pm | $45, 5 and under FREE


Saturday + Sunday

Grudge Fest @ Maryland International Raceway

There's sure to be all kinds of exciting action as drivers go head-to-head for the crown in grudge racing. 

12pm til midnight (Sat) and 10pm (Sun) | $25/adult $10/kid


Sunday

Sunday Family Fun Day Scavenger Hunt @ Historic St. Mary's MD City  

Become a "history detective” & search for information about the different outdoor exhibits to complete your scavenger hunt. 

10am-4pm | $10/ adult, $6/youth, FREE/ 5 and younger



This Weekend: August 18th, 19th, and 20th

Weekend Events

Lots of dragon-themed fun this weekend in Solomons! Come watch the boat races, browse the restaurants and food vendors, and enjoy some music after!


Friday

✨Salsa Dancing @ Port of Leonardtown Winery

Lessons from 6:30 PM - 7:15 PM, followed by open dancing until 10 PM; $30/ticket; tickets cover dancing, lesson, and one beverage


✨90's Night and live music @ Tiki Bar in Solomons

Performance by "Here's to the Night"

6:30 PM


Saturday

✨Dragon Boat Festival @ Solomons Island

Spectate and cheer for the paddlers as they compete throughout the day! Local businesses are offering dragon-themed beverages and foods, Calvert Marine Museum is hosting a miniature boat crafting session, and food trucks and vendors will be set up throughout the day.

Races start at 9 AM; FREE


✨St. Mary's Craft Beverage Festival @ Aeropark

Come to the St. Mary's Regional Airport Terminal Building to sample beers, wines, ciders, and unique beverages produced by local wineries and distilleries.

12 PM - 4:30 PM; $30 admission 


Concert with bands Rivalry and The Dynamos @ Leonardtown Wharf

Ride the trolley, walk, or arrive by boat to watch this free concert by the river in downtown Leonardtown!

5 PM - 8 PM; FREE


Sunday

✨Funfest @ Calvert Marine Museum

Mini golf, Dunk tank, face-painting, food vendors

11 AM - 2 PM; Mini golf rates $10 for adults, $5 for kids 12 and under

This Weekend: August 11th, 12th, and 13th

Weekend Events


Happy Weekend!


Southern Maryland is a little more relaxed after Mama Duck made her appearance. But there are some chill activities happening locally.


Friday

✨Finally Friday @ Coteau Vineyards

Come relax at the vineyard!

3-8pm


✨Summer Concert Series @ LaPlata Town Hall

Bring a blanket or lawn chair and enjoy the US Navy band the Cruisers. Food trucks available on site.

7-9pm


✨Sunset Cruise @ Leonardtown Wharf

Enjoy a sunset cruise on Breton Bay.

6:15-8:15pm; $35/person


Saturday

✨Farmers Markets!

Support our local farmers and creators at Homegrown Market, LaPlata, BAE, Chesapeake Beach, the Barns at New Market

9-1


✨Live Music + Eats @ Xella

Mo & Mary Mac play and Lauren’s Lumpia food truck will be on site!

12-5


✨Live Music @ Perigeaux Vineyard

Travis Colflesh plays rock, pop, and original songs.

3-6pm


✨Flower Happy Hour Workshop @ Jubilee Fermentations

Create your own beautiful floral arrangement.Ticket includes snips/pruners, instruction and a fully stocked flower bar. Wine/beer available for purchase on site.

4-5:30, $55/person


✨Sunset Cruise @ Leonardtown Wharf

Enjoy a sunset cruise on Breton Bay.

6:15-8:15pm; $35/person


Sunday

✨Live music @ TikiBar

Fizz takes the stage!

2-6

This Weekend: August 4th, 5th, and 6th

Weekend Events


Happy Weekend! The giant duck is here and there are so many other fun events happening this weekend!!


All Weekend

✨Wharf Fest @ Leonardtown

The worlds biggest rubber duck is at the wharf. Come see it and enjoy live music, food trucks, kids games + activities,

10-6pm Kids games + Activities at the Wharf


Friday + Saturday

✨Prince Frederick Fire Department Carnival

Carnival games, rides, and food!

6pm-11pm


Friday

✨Art Blooms After Hours Reception @ Annmarie Garden

Celebrate the 14th Annual opening of Art Blooms, a three-day floral design exhibit with live music, living Jackson Pollack statue, a scavenger hunt, food trucks, and complimentary rose spritzer.

5-8pm, $15/person advance, $18/person at the door


✨Sunset Cruise @ Leonardtown Wharf

Enjoy a sunset cruise on Breton Bay.

6:15-8:15pm; $35/person


Saturday

✨Italian Heritage Festival @ Leonardtown Fairground

Authentic Italian food, carnival games, bounce houses, Pet Friendly Pet Adoption and tons of shopping

11am-6pm


✨50th Anniversary of the Governors Cup Yacht Race @ St. Mary’s College

Live music, local food trucks, and waterfront fun to celebrate thes boats coming in from Annapolis.

8:30am-9pm


✨Live Music @ Port of Leonardtown

Faith Noel plays and Grizzly Mountain Grill food truck will be on site.

3-6pm, Free


✨Live Music @ Brudergarten

Unfinished Business band plays. Enjoy a beer and all the fun activities on site.

3-6pm free


✨Film on the Flight Line @ Patuxent River Naval Air Museum

Bring blankets and chairs to watch Top Gun. There will be a Q&A session prior to the film with real F-14 pilots and crew. The film will start at dusk.

7pm, $15/adult in advance, $20 at the door; $5/kid 4-12 in advance, $10 at the door, kids under 3 FREE


Sunday

✨National Lighthouse Weekend @ Piney Point Lighthouse

Enjoy tours of the museum, Potomac River Maritime Exhibit, lighthouse tower, the Keeper’s Quarters, and grounds.

10-5pm, FREE

This Weekend: July 28th, 29th, and 30th

Weekend Events

Happy Weekend! This weekend is full of some Southern Maryland distinctive events, from boat races to tractor pulls. As always, good music and food are available as well.


Sat + Sun

✨Bash on the Bay @ Leonardtown Wharf

Enjoy a weekend of vintage boat races. Food trucks on site. 

FREE


Friday

✨Food Truck Friday at Hollywood Volunteer Fire Department

Linda's on the Go, Old Towne Pub, Nicoletti's Streetzeria, Wildewood BBQ, Salted Scoop, Sweet Tooth Funnel , Cakes, Crabby Corn, Sweet Blue Smoke

4:30 PM-7:30 PM


Saturday

✨World Embroidery Day @ Historic St Mary’s City

Learn basic 17th-century embroidery techniques, no experience required. 

11am-12pm, workshop included in museum admission


✨Live music @ Perigeaux Winery

Enjoy live music in the beautiful vineyard. 

2-6pm


✨Battle By the Bay @ St. Mary’s County Fairgrounds

Truck & Tractor Pull, bring a lawn chair .Food trucks on site

6-9pm, $20/adult, $10/kid 5-12, under 5, free


✨Sunset Cruise @ Leonardtown Wharf

Enjoy breathtaking views of Breton Bay and St. Clements Island. 

6:15-8:15, $35/person


✨Jimmy Charles Band @ Tiki bar

Enjoy live music!

6:30-10


Sunday

✨Live Music @ Brudgerarten

Dynamo Jack plays pop, folk, alternative, country and rock!

3-6pm, free

This Weekend: July 14th, 15th, and 16th 

Weekend Events

Happy Weekend! Enjoy some indoor and outdoor adventures and finish the night with good food and drinks!


Friday


✨Open Roller-Skating @ Leonard Hall Rec Center

$5 entry, $2.50 for skate rentals; family friendly music and skating!

2 PM - 4 PM


✨River Concert @ St. Mary's College

Bring a lawn chair and listen to music on the water. Food trucks on site.

7-9pm, FREE


Saturday


✨Group Bike Ride @ Patuxent Adventure Center

Two bike routes available with speed groups ranging from casual to competitive paces; FREE

8 AM


✨Bar Crawl @ Leonardtown Square in memory of Firefighter Brice Trossbach

Live Music by Doc Martin and The Flannels 

7 PM -10 PM


✨Argentine Feast with Chef Katriel @ No Thyme to Cook

Multi-course meal served on the beach with cooking insights and instruction from the chef

6 PM - 9 PM; $150/ticket


Sunday


✨AeroPark Farmer’s Market @ SMC Regional Airport

Drive, bike, or fly to the market for fresh goods and produce

Hosted by Historic Sotterley

9 AM - 1 PM


✨Music @ Port of Leonardtown Winery

Swingaway Jazz Band

2 PM - 5 PM


All Weekend


✨Zinia Zuperbloom @ Goldpetal Farms

Food trucks and craft vendors in addition to access to the sunflower maze and fields of pick-your-own flowers

10 AM - Sunset; $15 general admission, kids 6 and under are FREE

This Weekend: July 7th, 8th, and 9th 

Weekend Events

Happy Weekend Everyone!


Here is a sampling of what's going on in Southern Maryland this weekend.


Lots of live music, sharks, and seafood!


Friday

✨First Friday @ Leonardtown Square

Eric Byrd Trio plays on the square

5-9pm


✨River Concert @ St. Mary's College

Bring a lawn chair and listen to music on the water. Food trucks on site.

7-9pm, FREE


Saturday

✨Farmers Market

Support your local farmers @ the Red Barn Farmers Market, BAE, Chesapeake Beach, or the Barns at New Market

9-1


✨Sharkfest @ Calvert Marine Museum

Celebrate all things related to sharks! Real sharks on site and lots of shark activities. 

10-5; $11/adult, $6/child


✨Live Music @ Running Hare Vineyard

John Luskey and Hyland Brothers take the stage at this beautiful vineyard. 

12-10pm


✨Live Music @ Xella Winery

Folk Salad plays and Farm.Fork.Soul food truck is on site!

1-4


✨Live Music @ Perigeaux Vineyard

Mike Heuer takes the stage

2-6


✨Contra Dancing @ Christ Church Parish Hall

Contra dance with an ice cream social at intermission.  

7-10pm, $12/person


Sunday

✨Family Fun Day-Breakfast with the Animals @ Historic St Marys

Help feed the animals and enjoy a guided tour of the Godiah Spray Tobacco Plantation.

10:30-11:30


✨Live Music @ Perigeaux Vineyard

Joe Norris takes the stage

2-6


All Weekend

✨Potomac Jazz and Seafood Festival @ St. Clements Office Museum

Relax waterside and 

enjoy live jazz artists + delicious seafood.4 

$85/person



This Weekend: June 30th,  July 1st and 2nd 

Weekend Events


Happy 4th of July Weekend!


There are fireworks happening every night this weekend and other fun events.


All Weekend

✨Into the Woods @ Newtowne Players

Opening Weekend!

Fri + Sat @ 8, Sun 3:30 $13-$18/person


Friday

✨River Concert @ St. Mary’s College

Enjoy live music on the water, food trucks, and fireworks. Bring your own chair

7pm, free


Saturday

✨Sunrise Yoga @ Leonardtown Wharf

Bring a donation to Three Oaks Shelter; register in advance

7:30am, FREE but bring a donation


✨Sea Glass and Craft Market @ Annmarie Garden

Beach-themed market celebrating all things summer

9-2


✨Live Music @ Perigeaux

Enjoy live music in the vineyards

2-6pm


✨July Drinks on the Beach @ NoThymetoCook

Listen to live music and grab a drink & delicious nibbles while sharing the space with friends

5-8pm, free


✨Manafest @ Last Drop Country Bar

Local artists playing at indoor and outdoor stages with axe throwing and glow party.

6pm, $10/person, doors open at 5pm


✨Film on the Flight Line @ Pax Naval Air Museum

Playing a variety of short films from their vast film collection. Bring chairs, snacks, and drinks!

7:30pm-9:30pm, $10/adult, $4/kid


Sunday

✨Live Music @ Running Hare Vineyard

1-5pm


✨Annual 4th of July Celebration @ Clarke’s Landing

California Ramblers play and fireworks at 9pm

5pm 


This Weekend: June 23rd, 24th, and 25th

Weekend Events


Happy Weekend!


There's tons of live music happening in Southern Maryland this weekend.


Friday

✨River Concert @ St. Mary's College

Bring a lawn chair and listen to music on the water. Food trucks on site.

7-9pm, FREE


Saturday

✨Beerfest @ Historic St Marys

Live music, food samples from local cuisine, and various regional craft brews. Family-friendly event.

12-8, $10-$35/person, kids under 15, FREE


✨Drink Maryland North Beach

Highlighting local craft beverages, crafters, food vendors, live music, pop-up open air market.

12-5, $20/erson


✨Calvert Bluegrass & Acoustic Music Festival @ Waters Memorial United Methodist Church

Local musicians and food truck, all proceeds support local wome’s’ shelter.

12-5 FREE


✨Live Music @ Running Hare

Hyland Brother and ShipWreckt play with Hungry Hare Food Truck on site.

12-9:30 pm


✨Live Music @ Generations Vineyard

Shane Graham plays, Mission BBQ food truck, Copper Compass Distillery, all to support Warfighter Advance.

1:30-4:30


✨Leonardtown Summer Music Festival @ Leonardtown Wharf

Bring a lawn chair and listen to Latrice Carr and the Rise Band show play. R&B line dance lessons.

5-8pm, FREE


Sunday

✨Live Music @ Running Hare

Summer Breeze plays with Hungry Hare Food Truck on site.

1-5pm


✨Live Music @ TikiBar

Night Cap takes the stage

2-6pm


Saturday + Sunday

Lavender Days Festival @ Susanna’s Watch

Live music, petting zoo, face painting, food trucks, beverage bar, vendors, floral workshops, etc all surrounded by beautiful lavender plants on a waterfront farm.

$35/person 


This Weekend: June 2nd, 3rd, and 4th

Weekend Events


Happy June Everyone!!!


Here's what's happening in Southern Maryland this weekend!!


Friday

✨First Friday in Leonardtown

Live music and special activities in the square.

5-8


✨Live Music @ Port of Leonardtown

Bootleggers play

5:30-8:30


Saturday

✨Sunrise Yoga @ Leonardtown Wharf

Bring a donation (cash or physical item) to donate to Animal Shelter or St. Mary’s County

7:30-8:30 am, free but must register in advance


✨Heritage Day @ St. Clements Island Museum

Discover the history + culture with crafts, games, demonstrations, lighthouse tours, traditional music, and more.

10-3, Free admission and taxi rides


✨Live Music & Eats @ Xella Winery

Music by Daniela + Farm.Fork.Soul food truck

12-5


✨Live Music @ Perigeaux

Susan St George plays!

2-6


✨Live music @ Tiki Bar

Shake the Room Rock band takes the stage

6:30pm


✨Comedy Night @ the Rex

Improv style comedy show with limited tickets left (forreal, I checked the site!)

8pm $12/person


Sunday

✨Summer Slice Party @ Slicehouse

Japanese City Pop by Juicebox Johnson and Japanese specials Tonkatsu pizza, Japanese beer, chu-hi cocktails

11-5


✨Children's Day on the Farm @ Jefferson Patterson Park

Celebrate St. Mary’s Rich cultural history with Demonstrations, hands-on activities, pony rides, games, live entertainment, food and beverages.

11-5, free


This Weekend: May 12th, 13th, and 14th

Weekend Events


Happy Mother's Day Weekend!


Here are some great events happening in Southern Maryland this weekend!


Friday

✨Friday Night on the Farm @ Lyon Family Farm

An evening of Strawberry picking with 8 food trucks, and face painting.

4-8pm


✨Plein Air Festival @ Leonardtown Wharf

Evening of community art. Bring your own supplies or join in on a community mural project. Live music and local food for purchase.

4:30-8:30, FREE


Saturday

✨Plant Sale @ Summerseat Farm

Tons of plants for sale with breakfast and lunch available for purchase

8-2pm


✨Mother’s Day Market @ Annmarie Garden

Tons of handmade, homegrown, and homemade gifts

9-2


✨Calvert Arts Fest @ All Saints Episocal Church

Local artisan gather with live music, food, wine and beer tasting

10-5; Entry is free but $20 for beer and wine tasting


✨Live Music @ Generations Vineyard

Shane Graham plays and Farm.Fork.Soul will have food for purchase

1:30-4:30


✨Live Music @ Perigeaux Winery

Folk Salad plays

2-6pm, FREE


✨Live Music @ Corteau Vineyards in Mechanicsville

Brian Lawrence plays and food truck onsite

3-6pm


✨2nd Monthly Community Coffee House @ St George's Episcopal Parish Hall

Come perform or support local artists!

5-8pm, FREE


Sunday

✨Free Admission for Moms @ St. Mary’s County Museums

Participating museums: St. Clements Island Museum, Piney Point Lighthouse, Old Jail Museum

All Day Sunday


✨Goat Trail Walking @ Hope the Goat in Prince Frederick

Enjoy a quiet trail walk with goats!

1-2pm, $14/person, sign up online


✨Live Music @ Perigeaux Winery

Susan St. George is playing

2-6pm, Free 


This Weekend: May 5th, 6th, and 7th

Weekend Events


Happy Cinco de Mayo weekend everyone!


There are so many fun events happening in SOMD this weekend!


All Weekend

✨Spring Festival @ St. Mary’s County Fairgrounds

Carnival rides, live music, entertainment, food, yard sale, tractor pull

Fri 5-10pm, Sat 10am-10pm, Sun 10am-6pm; FREE, tickets for rides are $1.25/each


✨These Shining Lives @ Three Notch Theater

Come see the Newtowne Players newest production.

Fri + Sat 8pm, Sun 3:30 pm


Friday

✨Cinco de Mayo First Friday in Leonardtown

Community art show, fun events, and restaurants are open later.

5-8


✨Open house @ Fen Holistic in Leonardtown

Amazing vendors: coffee, food, flowers, photographer + more.

4-7pm


✨After Hours @ Annmarie Garden.

Opening Reception for a new exhibit with live music and food trucks.

5-7pm, $5/person, members free


Saturday

✨International Women’s Mountain Bike Day @ St. Mary’s River State Park

Ride the trail with other women. Coffee, snacks, small skills clinic, and bike mechanic on site.Email joey@pacpaddle.com if you need to borrow a bike.

9am, FREE


✨May Day @ Historic St. Mary’s

Celebrate spring with May Day traditions: play games from the 17th century + hands-on nature activities.

10 am - 4pm. $10/person, $6 (6-18), under 5 FREE


✨Solomons Maritime Festival @ Calvert Marine Museum

Antique boats and motors, cooking demonstrations, traditional music, toy boat building, and boat rides offer something for all members of the family! Free 30-minute cruises on the Wm. B. Tennison.

10-4pm, FREE


✨Truck Mania @ Maryland International Raceway

Massive truck show, races, Daisy Dukes Challenge, burnout challenge.

10-8pm, $25/person, $10 (12-15), $5 (6-11)


✨Cosmic Symphony Concert @ St. Mary’s College

“Love and Loss”, our county orchestra performs with Blue Wind selling refreshments.

3-4:30, FREE 

This Weekend: April 28th, 29th, and 30th

Weekend Events


Get in some highland games, music, and fun in between the rain this weekend!


Friday

✨Lulu's Fate Maritime Performance Series at Calvert Marine Museum

Appalachian and country blues musical performance; covers and original music

7 PM - 9 PM

$25 admission


Saturday

✨ Southern Maryland Celtic Festival at Jefferson Patterson Park

Rugby, Highland games, craft demonstrations, food and activities

10 AM - 6 PM Rain or shine

$25 admission for adults, FREE admission for kids under 12 with an adult ticket


✨ Island Vibes Weekend @ Tiki Bar in Solomons

Headlining Band Ballyhoo @ 8 PM; Other performances by Harbor Boys (5 PM) and Sons of Pirates (Sunday at 2 PM)


✨ Leonardtown Summer Music Festival @ Leonardtown Wharf

Free performance by Leonardo Garcia Y Son Horizonte

6 PM - 8 PM

FREE Admission


Sunday

✨Spring Fling Car Show @ Leonardtown Square

Check out the range of vintage cars, hot rods, and other vehicles and enjoy food and other festivities

8 AM - 4 PM

$3 Spectator Admission

This Weekend: April 21st, 22nd, and 23rd

Weekend Events


Southern Maryland is showing up strong for Earth Day this year!


There really are SO many great events happening this weekend.


Friday

✨Leonardtown Luau/Bar Crawl

Live music, DJs, specialty drinks and fun activities in restaurants throughout L-town

12pm-12am


✨Live music @ Social Fenwick

Krys Baker + Becky Titus perform

3-7


✨Luau Party @ Brudegarten

Djs, hula dancers (at 8), axe throwing, cocktails, great food!

5pm-midnight


Saturday

✨Earth Arts Fest @ Annmarie Garden

Nature experiences, earth art, inspired learning, kids activities, music, food trucks, drinks, and green shopping. Annmarie Garden literally has the BEST festivals and we are so excited about their newest one!

9-2, $5/person, members FREE


✨Leonardtown Earth Day Celebration @ Leonardtown Square

Neighborhood litter cleanup, a clothing swap, free yoga and kayak demos, planting, live music, organic and Vegan food offerings, art great activities!

Starts at 9 and lasts all day


✨Earth Day Celebration @ Summerseat Farm

Exhibits, local farmers' market, recycled or repurposed arts and crafts, and info on sustainable living

11-4, FREE


✨Live Music @ Port of Leonardtown

Earth Day music by David Sparrow and food from Jamaican Grill

12-5pm, FREE but wine is encouraged :)


✨Opening Weekend for Tiki Bar in Solomons

Reagan Years 80s Tribute Band kicks off the weekend and there’s an allstar line-up of bands all day.

1pm-midnight


✨Live Music @ Generations Vineyard

Folk Salad performs at the vineyard!

1:30-4:30, FREE but wine is encouraged :)


✨Live Music @ Perigeaux

Susan StGeorge plays classic pop, rock, folk songs and top hits from the 80s, 90s + 2000s!

2-6pm


✨Plein Air Painting @ Leonardtown Wharf

Painting, wine, food, ice cream, mousic

4:30-7:30


✨Relay for Life Remembrance Walk @ St Marys College

Remembrance walk, Zumba, fun activities, performances, food trucks at the athletic center.

6-9pm


✨US Navy Band Sea Chanters @ St Mary’s College

20 person choral group performing at Dodge Performing Arts

7-8:30, FREE


Sunday

✨Evolve Yoga and Wellness @ Leonardtown Wharf

9:30 a.m. – 10:30 a.m.


✨Live music @ Port of Leonardtown Winery featuring the Billy Breslin from

2 p.m. - 5 p.m.FREE, but wine is encouraged :) 

This Weekend: April 14th, 15th, and 16th

Weekend Events


So many great events with food and music this weekend! Indoor and outdoor options, so make plans for rain or shine!


Friday

✨Dinner @ Enso’s

Beef + Vegetarian with a side of homemade chips to benefit Chancellors Point Club

5-7:30


✨Live Music with James Cornet @ Generations Vineyard

5:30-8:30


Saturday

✨Asian American Pacific Islander Cultural Festival @ Prince Frederick Library

dancing, food, art projects, games, etc celebrating this heritage

10-2, FREE


✨Chopteeth Afrofunk Big Band Concert

7-8:30pm; $10/person


Sunday

✨Spring Kids Bingo @ Ridge Volunteer Fire Department

Bingo for kids with great prizes!

1pm


✨Southern Maryland Bluegrass Festival @ Calvert Elks Lodge #2620

High Fidelity Performs

2-5pm; $20/person, kids under 12 FREE

This Weekend: March 31st and April 1st and 2nd

Weekend Events


Friday

Comedy Juggler: Michael Rosman @ The Rex

Unique show combining comedy, juggling, circus performing, and magic. This looks SO good. 

8pm, $20/person-$125/person


Saturday

Growing for Good Planting Day @ Sotterly

Help plant acres of potatoes that will be given to local food pantries. 

9-12, kids 5+ welcome to help!


3rd annual First Landing Wine & Arts Festival

Wine, music, crafts, kids activities, food trucks 

10-5pm, event entry is FREE but additional costs 


Easter Extravaganze @ Town Market in  Leonardtown 

Easter bunny, egg decorating, petting zoo, tons of vendors!

10-3


Community Easter Egg Hunt @ Real Life Church

Egg hunt, face painting, bounce house, games, crafts, face painting, food trucks. 

10am, FREE


Maryland Osprey & Nature Festival @ Drum Point Circle

See live raptors up close, attend lectures with wildlife experts, birdwatching, live music, food trucks, and FREE Rita’s Italian Ice to children. Parking at Drum Point Club is limited. Overflow parking will be at Patuxent High School and a shuttle bus will provide transportation.

11-4, $5/person, $10/family


Easter Egg Festival @ St Mary’s County Fairgrounds

Egg hunts, arts and crafts, face painting, entertaining performers, tasty food trucks, products and craft exhibitors, Easter Bunny

11:30-4; $5/child


Opening Weekend @ Running Hare

Live music and food trucks to celebrate the opening weekend

12-9, 21+ $5/person cover charge 


Annual Easter Bunny Visit @ Ruddy Duck Brewery 

Easter bunny photos, complimentary crafts, casual egg hunt

2-4pm, FREE


Bowling with the Easter Bunny @ Lord Calvert Bowl

Bowl with Easter Bunny, egg hunt, fun activities

3:30-5:30pm


The Art of Listening Lecture @ St Marys College

Ann Deavere Smith an actor, playwright, and professor will lecture and do a book signing at the new Dodge performing arts building

7-8:30, FREE


Sunday

Coffee & Cars Season Opener @ Laurel Glen Parking Lot

Car hobby enthusiasts can gather with their cars and enjoy coffee.

8-12


Opening Weekend @ Running Hare

Live music and food trucks to celebrate the opening weekend

12-6, 21+ $5/person cover charge 


Modern Miami Fusion @ Pier450

Three Course, Prix Fixe chef’s tasting menu inspired by Miami. 

6-8pm, $54/person

This Weekend: March 24th, 25th, and 26th

Maryland day weekend is here!! Check out these amazing events!


Opening Weekend for Music Man @ Leonardtown High School

Amazing show out on by high schoolers!!!

7pm, $8/students; $12/adults


Final weekend of Grease @ Great Mills High School

Incredible show put on by high schoolers!!

7pm Fri, 12pm + 7pm Sat


Friday

Live Music @ Port of Leonardtown

2-5pm


Teen Take Over @ Annmarie Arts

Art, music, and food

7-10pm FREE, but for teens only


Comedy Night @ Taphouse1637

Enjoying laughing with 6 stand up comedians!

8:30pm, $15/person


Saturday

OtterMania @ Calvert Marine Museum

So many fun activities to learn about otters!

10-5pm; $11/adult, $6/kid


Maryland Day @ St Clements Island

Food trucks, special exhibits, public ceremony

10-5, FREE admissions and water taxi rides (9-2)


Maryland Day @ Historic St Mary’s City

Soap making, new MD Dove, hide tanning, 17th century games

10-4; ceremony at 1pm, $10/adults, $6/kids (6-18)


Savor Solomons Food Truck Fest

Come out to Solomons and eat well with a ton of food trucks!

11-5


Wine & Girl Scout Cooking Pairing @ Xella Winery

Wine and Girl Scout cookies in a beautiful setting!

12-5


Maryland Day Celebration @ St Mary’s County Library

Crafts + activities celebrating MD

1-2pm, Ideal for elementary school kids


Squid Inc @ Social

Live music and great drinks!

7-10pm


Sunday

Breakfast with the Easter Bunny @ Solomons Volunteer Rescue

9-11 Kids under 12, FREE


This Weekend: March 17th, 18th, and 19th

Weekend Events


Opening weekend for Grease @ Great Mills High School


$12/adults, $8/ students

Fri + Sat @ 7pm


Friday

Throw Like a Leprechaun @ Brudergarten 

Viking Axe throwing. 

12pm-12am


St. Patrick’s Day Celebration @ Brick WFB

Live music, giveaways, food specials

2-9pm


MC Hammer @ Social Fenwick

Jack McNutt and David Hammer playing

8pm-12am; doors open @ 7


St Patrick’s Day Celebration @ Tiki Bar

Live music and $3 drink specials

3pm-12am


St. Patrick’s Day Celebration @ Ruddy Duck Brewery

12pm-10pm


St Patrick's Day Celebration @ Pier450

Special menu, Irish cocktails, celebrations!

4-10pm


St Patty’s Day @ Olde Town Pub 

Live music and drink specials

4-10pm


St . Paddy’s Weekend @ Taphouse1637

Live music and drink specials

8-12, FREE



Saturday

Leprechaun Hunt @ ACLT Northside Trail 

Scavenger hunt, solve all the clues and receive your treasure

10am-3pm; $5/family, register online


Cherry Blossom Festival @ Lexington Manor Passive Park

Performances, activities, food trucks, and more!

12-4pm, FREE


Saint Patrick’s Celebration @ Perigeaux 

Live music, wine, and plat of Mediterranean or Irish Food

12-5pm, $40/person


St . Paddy’s Weekend @ Taphouse1637

Live music and drink specials

2pm-12am, FREE


This Weekend: March 10th, 11th, and 12th

Weekend events!


Friday

Live Music and Bowling at Lord Calvert Bowling Center

10 PM - 12 AM


Once Upon a Mattress - Musical Comedy by Port Tobacco Players

Port Tobacco Players in La Plata, MD

8 PM - 10:30 PM


Saturday

STEAM Day at Patuxent River Naval Air Museum

Multiple interactive exhibits presented by local vendors representing organizations involved with Science, Technology, Engineering, Art, and Math.

10 AM - 3 PM

Free Admission for children under 13 and high school students with a valid school ID; $10 admission for adults


Concert by Cosmic Symphony - The Life of an Artist

St. Mary's College Performing Arts Center

3 PM

Free Admission - Donations Appreciated


Saturday and Sunday

R.A.D. Self Defense Class for Women and Teens

Free class to learn new skills to protect yourself and others

Lexington Park Library

Register Here!

March 11th 10 AM - 4:30 PM

March 12th 1:30 PM - 4:30 PM


This Weekend: March 3rd, 4th, and 5th

Weekend events!


Friday

After hours @ Annmarie Gardens

Opening Reception for new exhibit. Enjoy Hot Dog Hideout food truck. 

5-7pm


First Friday @ Leonardtown Square

4-8


Live Music @ Port of Leonardtown 

Farm.Fork.Soul Food Truck

5:30-8:30


SMCM Orchestra Concert @ St. Mary's College of Maryland

Listen to great music in the new Dodge Performing Arts Auditorium

7pm, FREE


Saturday and Sunday

Food Truck + Live Music @ Port of Leonardtown

2-5


Solo Performance by the Piano Man @ Taphouse 1637

8pm, $10/person


Sunday

Annapolis St Patrick's Day Parade

1-3pm

This Weekend: February 24th, 25th, and 26th

Weekend events!


All Weekend 

Moll Dyer Weekend in Leonardtown

Opening ceremony @ Tudor Hall Manor, scavenger hunt, ghost walk, Moll Dyer Cocktail contest at local restaurants, free trolley, crafting

Events start Friday @ 6 PM and last all weekend


Friday

Carnaval Celebration @ Ruddy Duck Brewery and Grill in Solomons

Enjoy Brazilian-themed specials; Entertainment and Samba Dancing!

7-10 PM


Saturday

Puppy Yoga @ Hypehouse Cycle and Fitness

Spend time playing with puppies looking to be adopted and get a yoga workout in! Sign up for the class through their portal here.

11 AM - 12 PM, $15 for the class


SMMB Trail Fundraiser and Winter Social @ Patuxent Adventure Center

Fundraiser for tools and materials to maintain St Mary's River Trails. Potluck, socialize, and learn about St Mary's River State Park

4-7, FREE 


BRU Winter Games @ Brugarten

Compete for prizes in Cornhole, Pyramid Stack, Paper Pull, Kan-Jam, Axe Throwing

12-4 


Salsa Dancing @ Port of Leonardtown Winery

All skill levels are welcome to dance at the winery!

6-9:30 $30/person includes glass of wine and lesson


Improv Comedy Show with Somd Improv Comedy Club @ Last Drop Country Bar

A “Whose Line Is It Anyway” style show with stand-up comics from the DMV and SOMD’s local improv comedy troupe.

7 PM - 9 PM, $16.49/ticket


Sunday

SMMB Sunday Social Ride @ St Mary’s Lake

Show up and ride the trails!

9 am, FREE to ride, but there is a $3/car park entry fee. 

This Weekend: February 17th, 18th, and 19th

Weekend events!


Saturday

Show Some Love Unguided Tour @ American Chestnut Land Trails

Hike the trails and hunt for painted rocks. 

Trails open at 8am. FREE


Spirit of Southern Maryland @ Pax Naval Air Museum

Sample incredible distilled spirits, learn about preparing unique cocktails, and experience hand-crafted cocktail mixers–all while learning about this awesome local industry.

1:30-7; $40-$55/person



Sunday

Family Skate @ Leonard Rec Center

Come out and roller skate!

2-5; $5/person, $2.50/skates


Fly4ACure Winter Festival @ Leonardtown High School

carnival games, food trucks, and raffles to support the Leukemia & Lymphoma Society. Fun for the whole family!

$10/person, children under 4 FREE


All Weekend!

Sound of Music @ Newtowne Players

$18/person, $13/child

8pm, Fri + Sat

3:30pm, Sun



This Weekend: February 10th, 11th, and 12th

The groundhog says it's not spring yet, but in SoMD it feels like the weather has turned. Get out and enjoy it!


Friday


After Hours @ Annmarie Art

Celebration of two new exhibits with live music by Johnny Placido, a signature cocktail "Valentine Spritzer", Dan D's Catering & Concessions food truck

5-7pm; $5/person; FREE for members


Saturday


Valentine Maker's Market @ Annmarie Gardens

Find thoughtful and locally made gifts, and homegrown products. Food truck too! 

9-2, FREE


Hot for Chocolate 5k Race @ Jefferson Patterson

5k Race to benefit Project Echo and friend of JPP.

8am; $40/person


Bowling Day in the USA @ Lord Calvert Bowl

Buy 2, get 1 free games, face painting, decorate a bowling pin, and other games and activities.

12-3pm, free


Live Music @ Port of Leonardtown

Music + Food Truck

1-5


Southern Maryland Bluegrass @ Elks Lodge in Prince Frederick

Award winning Lonesome River Boys Band takes the stage

2pm, $20/person, kids under 12 free with paying adult


Contra Dance @ Christ Episcopal Church Parish Hall

SOMD Traditional Dance and Music is hosting a Contra Dance!

7-10pm; class @ 7, dance starts @ 7:30


Sunday


Show Some Love Unguided Hike @ American Chesnut Land Trust Trail

Hunt for painted rocks on your hike and share with captions of what you love about park, stream, or your sweetheart.

Starts at 8am and lasts all day.


Live Music @ Port of Leonardtown

Music + Food Truck

1PM-5PM


All Weekend 


Valentine Flower Pop Up Shop @ Marie and Nash

Sat 10-5, Sun 10-4. Tues 10-5


Sound of Music @ Newtowne Players

$18/person, $13/child

8pm, Fri + Sat

3:30pm, Sun


Tues Feb 14th


Valentines Comedy Dinner @ Antoinette’s Garden

Comedy show with Huggy Lowdown! Ticket includes dinner, dessert, 1 bottle of wine and champagne toast

9-11; $50/person

This Weekend: February 3rd, 4th, and 5th

Happy Friday! Lots of indoor opportunities for a cold February weekend!

Friday

First Friday @ Leonardtown

 

Port of Leonardtown 

Swing Away, Gato Tacos @ Port of Leonardtown


Saturday

Cover your 6- Chaptico Market @ Port of Leonardtown


Winter Blast  @ Hollywood Vol Fire Department

Pro wrestling event with a Meet and Greet with current and former pro wrestlers.

Doors open @ 6, event starts at 7:30


 Sunday 

John Luskey-Heidi’s Eats @ Port of Leonardtown


Barre, Breathe and Create event along with Quality Street Kitchen and Board & Brush! When: February 5th 5pm-8pm Cost: $73/person

This Weekend: January 27th, 28th, and 29th

It's FRIDAY and you guessed it, time for your weekly SOMD weekend events!!


Friday

✨Drop in Basketball 50+yrs @ Willows Rec Center


Saturday

Good Morning Yoga @ Calvert Health Medical Center

8:30, $12/person

Appraiser Fair at St. Clement's Island Museum

Bring your treasured possession to have expert appraisers determine their value

Appraisers for various types of items will be available at the museum. Appraisers for fine arts, coins and currency.

10-3, free but $5/appraisal

✨Winter Classic Viking Tournament @ Bru

Ax throwing competition with prizes. Call to register: 240-346-9654

2pm

✨Music @ Port of Leonardtown

Nightcap is performing and Heidi's Eats & Sages Treats will be available onsite for food!

2-5pm

Southern Maryland Traditional Music and Dance Open Mic Night @ Christ Church Parish Hall

Acoustic music performed by local talented singers and songwriters.

7-10pm, $7/person (unless you’re performing!)

✨Hammer & McNutt @ Social

Listen to great music and enjoy great drinks!

7pm

✨Reggie Rice @ The Rex Theater

Comedy night at the new theater in Leonardtown!

8:30-10:30, $20/person 

This Weekend: January 20th, 21st, and 22nd

Happy Friday! Here is a quick sampling of local events for southern Maryland this weekend. In between showings and an open house this weekend, you might run into us at Clarke's Landing for some light rugby practice or Port of Leonardtown for some free music!

Friday

Blind Draw Volleyball Tournament @ Willows Rec Center

$30 Adults/ $25 Students if registering today; Sign up as an individual and choose your division!

7:00 PM

Stand Up Comedy @ Taphouse 1637

$15 for tickets

8:30 PM


Saturday

✨Glow-N-Dark and Laser Tag Party @ My Gym

Laser tag, gymnastics, tumbling, crafts, a movie on a blow-up screen, and pizza provided!

$40 or $45 for non-members

6:00PM-9:30 PM

✨Pre-Season Touch Rugby Practice and Fitness Conditioning with Pax River Rugby

Open to anyone! No experience needed; men, women, and children are welcome to come learn the sport, meet team members, and get some good conditioning in!

11:00 AM - 1:00 PM


Sunday

Live music at Port of Leonardtown Winery - Doc Lohn

Music is free! Food truck from Grizzly Mountain BBQ

2-5 PM

This Weekend: January 6th, 7th, and 8th

Happy Weekend!

Lots of local businesses are taking a *much deserved* winter break so there are fewer events happening on the first weekend of January 2023.


Friday

First Friday in Leonardtown

Come out and Support local businesses and enjoy a fun atmosphere!

5-8pm

Live Music @ Port of Leonardtown

Mulled wine, hot chocolate, wine tastings

6:30-8:30


Saturday

✨Farmers Markets

Homegrown Market 

9-1

✨Explore Calvert Cliffs

3.6 Mile Hike and Fossil Hunting

10-12, $5/car

✨Exhibition Reception @ ArtWorks@7th

See how local artists respond to their own “cabin fever”. Light refreshments will be served

1-4

Live Music @ Port of Leonardtown

Mulled wine, hot chocolate, wine tastings

music by Joe Parsons; food from Heidi's Eats & Sage's Treats

2-5 

This Weekend: December 16th, 17th, and 18th

School's out and it's almost officially winter! Check out some of our recommendations for holiday cheer and let us know if we missed something good! We will be glad to update and share!

Friday

🌲1637 Taphouse

Music Trivia

8 - 9 PM

Saturday

🌲Perigeaux Vineyards and Winery

Holiday Open House - Complimentary holiday cookies and mulled wine!

12 - 6 PM

🌲Pier 450

Winter Beach Happy Hour - Christmas lights, hot chocolate, spiked eggnog, and special holiday martinis

3:30 PM - 5:30 PM

Sunday

🌲No Thyme to Cook

Holiday Market - Local artisans and photos with Santa!

11 - 4 PM

This Weekend: December 9th, 10th, and 11th

Sorry for the delay in getting out the weekly events! We had a week of sickness (the only one NOT affected was Ari) that really cramped our style.

But there's LOADS of fun events happening this weekend to get you in the holiday season. Tell us what you're up to this weekend in the comments!

Saturday

🌲Annmarie Holiday Market

Shop from tons of great local vendors!

9-2

🌲1st Season Celebration @ Two Lions Vineyard

Wine flights, mulled wine, Beezknees Ice cream, Honey Boards Charcuterie

11:30-6

🌲Vintage Christmas Market @ Wildberry Farm + Market

Santa, light walk, beer garden, unique gifts

3-7pm

🌲Cosmic Symphony Concert @ Patuxent Presbyterian Church

3-4:30 pm, FREE

🌲Solomons Christmas Walk + Lighted Boat Parade

4-9pm; boat parade starts @ 6

🌲Chesapeake Beach Holiday Lights Tour

5-8pm

🌲Annmarie Garden in Lights

5-9pm

🌲Madrigal Dinner @ Historic St Marys

Cocktails, apps, dinner, and choral concert

6pm, $130/person, register in advance

🌲Clue @ Newtowne Neck Theaters

8-10pm, $13/person


Sunday

🌲St. Clements Island Museum Doll + Train Exhibit

10-5

🌲Gingerbread Bash @ Lexington Park Methodist Church

Build a Gingerbread Nativity Scene

12-2, FREE , register in advance

🌲Cosmic Symphony Concert @St. John Vianney Catholic Church

3-4:30 pm, FREE


🌲Clue @ Newtowne Neck Theaters

3:30-5:30 pm, $13/person 

This Weekend: December 2nd, 3rd, and 4th

December is here, and Southern Maryland does a lot to celebrate it! Join in the celebrations this weekend!

Friday

1st Friday @ Leonardtown Square 

Live Music, Local craft markets, Art, and axe throwing!

 

Saturday

Saturday Holiday Market @ The Barns at New Market in Mechanicsville

9:00 AM - 4:00 PM


Sunday

Holiday Open House @ St. Clement's Museum

Children's games, music, and refreshments!


All Weekend

Garden in Lights @ Annmarie Garden

The lights are up! Beautiful, unique light displays throughout the garden paths. Sign up ahead of time and bring all the kids!

This Weekend: November 18th, 19th, and 20th

Happy Almost Thanksgiving Weekend!

Way more fun events happening this weekend than we were expecting!!!


Saturday

26th Annual Thanksgiving 5k @ Historic St. Mary’s

5k race, prediction 5k, and fun run with all proceeds going to Special Olympics

8:30am


Guided Hiking Tour @ Jefferson Patterson Park

Meet at the visitor center parking lot and hike through the ground and learn about the 9,000 years of history uncovered through the park.

10-12:30, FREE


Wine Tasting @ Two Lions Vineyard

Bring a picnic and enjoy live music. Icecream and charcuterie available for purchase.

11:30-5


PAC and Jubilee Social Ride @ Jubilee Farm

2 mile relaxed bike course followed by socializing, beer, and a pot luck-bring a side dish if you’d like!

3-6pm, FREE


The Park at Dark @ Jefferson Patterson Park

Enjoy a guide for a 1-mile lantern-lit walk of the Park.

5:30pm; $10 per group/family


Dinner & A Movie @ NoThymeToCook

Watch Clue and enjoy a 3-Course meal from food featured in the film.

6-9pm, $75


Swing Dance Social with Beginner Lesson @ St. John’s

7-8 swing lesson, 8-10 open dancing

7-10pm, FREE


Pre-Thanksgiving Extravaganza @ the Green Door

Awesome live music!

8pm, $5/person, 21+


Sunday

Bow + Throw @ Bru

Kids of all ages can throw kid-sized axes and decorate and learn to shoot their own bows. All materials and instruction included.

1-4pm


Saturday and Sunday

Live Music @ Port of Leonardtown

2-5 

This Weekend: November 11th, 12th, and 13th

Happy Weekend Friends!

Here are the highlights of what's happening in Southern Maryland this weekend!


Friday

Food Truck & Live Music @ Generations Vineyard

Chaptico Market & Justin Allen

5-8:30


Robbie Boothe Band Farewell Show @ Hollywood Firehouse

Great music and food and drinks on site

6-9pm $10/person 18+. $5/person 6-17yrs


Saturday

Coastal Arts Market @ Leonardtown Wharf

Makers Market

9-3


NovemBEER @ Historic Sotterley

Lawn Game, live music, artisan vendors, beer and wine

1-5pm $25/person, kids under 6 FREE


Live Music @ Port of Leonardtown 1-5

Running Hare 1-4


Happy Birthday to USMC @ Bru

Cake Cutting Celebration open to the public

7pm


Sunday

15th Annual Ornament Show & Sale @ Annmarie Gardens

10–5pm


Chef’s Tasting @ Pier450

3 course meal highlighting Afghan hospitality.

5:30pm, $48/person, order in advance


Don't forget to support our local farmers at the farmers markets throughout Southern Maryland on Saturday morning!

This Weekend: November 4th, 5th, and 6th

Happy Weekend! How in the world is it already November?!

Here are the events you don't want to miss this weekend:


Friday

✨First Friday @ Leonardtown Square

Music, food, shopping, fun activities in the square!

5-10pm


Saturday

War of 1812 Invasion Demonstration @ Point Lookout

Costumed Interpreters will provide living history programs, exhibits and firing demonstrations about the War of 1812 Invasion.

9-4, $3/car

✨Goat Yoga @ Prosperity Farms, Sunderland MD

Yoga + Goat Snuggles.

10-11am, $35/person, purchase in advance

American Indian Heritage Day @ Jefferson Patterson

Local native dancers, educational demonstrations, and tons of activities!

11-4, FREE

Annual Community Carnival, Craft & Vendor Fair @ KCA

40+ carnival games, including a Zip Line, Pony Rides, Big Baller, Mobile Ninja Warrior Obstacle Course, Laser Tag! 30+ Crafters & Vendors. Food for sale.

12-6pm, FREE

✨Justin Taylor Band @ Last Drop Country Bar

9-1am; $5/person


All Weekend

Haltech World Cup Finals @ Maryland International Raceway

This five-day event attracts racers from over ten different countries who race for a financial prize pool of over $180,000.

$35/person


PLUS Live music @ all the local wineries.

This Weekend: October 28th, 29th, and 30th

So Many Fun events happening in Southern Maryland this weekend!!!


Friday

✨Grown Up Halloween Beach Bash @ Pier450

Includes appetizers and 1 drink, plus DJ, fire pits, costume contest and more!

7-11, $40/person


✨Halloween Dance Party @ Slicehouse II Go

9pm-2am


Saturday

Halloween Party @ Bru 1pm-

Axe throwing (8pm), DJ(9pm), costume costume(10pm), Smash House burgers (1pm)


Fright Line @ Pax River Naval Air Museum

Trick or Treat, Arts + crafts

2-3:30 Kids in costume, FREE, adults $7


Halloween Family Fun Night @ Kellam’s Field

Trick or Treating, live music, movie showing- Hotel Transylvania (6:30pm)

5-8:30


LITVAR live in concert 7pm @ St. Inie’s


Monday (Halloween)

Trick or Treat @ the Wildewood Center

4:30-6:30pm; Come in Costume for trick or treating from the shops!


✨Fall Fest @ Cornerstone Presbyterian Church

Trunk or treat, moon bounce, games, activities, and free dinner + hot cocoa by the firepit!

5-7pm, FREE


Fri + Sat

As You Like it @ Chopticon High School

6pm; $10/person


Sat + Sun

Cosmic Symphony’s a Haunting Return

Pax Presbyterian Church Sat @ 3:pm

St. John Vianney Life Center Sun @ 3pm FREE


Nightmare on Sotterley Lane @ Sotterley Plantation!

A walking tour of some of their favorite creepy spaces and places.

7pm, $15/person, Recommended ages 8+, order tickets online 

This Weekend: October 21st, 22nd, and 23rd

It’s getting chillier, but with a sweater or flannel, you will still be able to enjoy some Halloween thrills and fall festivities in southern Maryland this weekend!

Friday

✨Chopteeth Afrofunk Big Band @ St. Mary’s College of MD

12 piece band bringing the funk to SMCM’s new performing arts building.

7-8:30; $12-$25/person

Saturday

Halloween Movie Fest @ Port of Leonardtown Park, 5:00 PM - 8:30 PM. Enjoy a costume contest, trick-or-treating, kids activities, and a free movie showing. This is probably more our speed.

✨St. Mary's County STE(A)M Festival @ St. Mary’s Fairgrounds

Fun activities for kids of all ages, interactive, hands-on experiences, food trucks, and more.

10-2pm, Free


✨Fun on the Farm @ Summerseat Farms

Buffalo, farm animals, hayrides. Games, pumpkin painting, picnic concert

11-3; $10/fam suggested donation


Fri+ Sat Night


Nightmare on Sotterley Lane @ Sotterley Plantation!

A walking tour of some of their favorite creepy spaces and places.

7pm, $15/person, Recommended ages 8+, order tickets online

Sunday

Make S’Mores @ Brudergarten, 11:00 AM - 6:00 PM. They have campfire rings set up outside and S’mores kits available for purchase!

Oktoberfests


✨Oktoberfest @ Southern MD Biergarten + Running Hare

live music, delicious food + beer!

Fri: 4-10, Sat 12-10pm, Sun 12-8pm


✨Oktoberfest @ Susanna’s Watch

Great German food, drink, songs, live music, photo booth included in the price.

Dress like a Bavarian!

11-6; $135/person, reserve tickets online


Trick or Treats


✨Halloween in the Garden @ Annmarie Gardens

Trick or Treat through the Gardens!

10-4pm; $5/non-members; reserve tickets in advance.


✨Trunk or Treat @ St. Mary’s Fairground

Come in your best costume + snag some goodies and treats.

2-5pm, $2person


✨Trick or Treat @ Historic St. Marys

The trick-or-treating event will weave through the Town Center area, with games + pirates

5-8pm. FREE


✨Trunk or Treat @ Port of Leonardtown Park

Trick or treating followed by a screening of Beetlejuice at 6:30

5-6:30

This Weekend: October 14th, 15th, and 16th

It’s going to be a beautiful weekend so take advantage of this great weather and spend time outside at one of these LOCAL events.


Quick word about the Oyster Fest- unpopular view: we are NOT oyster people and we LOVE the Oyster Fest. It is the epitome of small town festival that draws 11,000 people over the weekend. National oyster shucking competition and the winner goes to the WORLD oyster shucking championship and look for the oyster king + queen.


Here are some bonus details about some of these events:


Oyster Fest- 10-5 National oyster shucking competition, celebration of oysters, family-friendly shows, live music local vendors, beer tent.

$15/day; $20/two-day pass. Kids under 10 FREE


Sotterley- pumpkin painting, sensory bins, corn hole, basketball and more. Small pumpkin for all kids 12 and under

$5/person. Under 6 FREE


✨Blacksmithing @ Jefferson Patterson

Learn the basics of blacksmithing and make your own fire poker. $40/person


✨Don’t like anything you see?

Walk around Leonardtown square which is looking particularly spooky and pick up a Basic Witch Latte from Social and Euphoria Bakehouse macarons at Heritage Chocolates. Or throw axes and drink great beer at Brugarten. 

This Weekend: October 7th, 8th, and 9th

Saturdays are for Oktoberfest and Sundays are for cruises.


Here are some more details about all the fun events happening in SOMD this weekend. Share with a friend!!


Friday


Fall Crawl in Leonardtown 1-7pm

Special Food + Drink and live Music all afternoon @ Olde Town Pub, Brüdergarten, The Front Porch, Social Coffeehouse Antoinette’s,The Rex, The Slice House


Saturday


Craft + Storytime @ Dean Lumber 9am

Craft, story, and snack. FREE


✨Pumpkin and Apple Cider Donuts @ Forest Hall Farm. Go a little early before they sell out!

Pumpkin Patch, animals, play area $9/person


✨Artisan Fair @ Greenwell 9-3

Crafts fair with multiple vendors, pony rides, food trucks in a beautiful park setting


Patuxent river appreciation day @ Calvert Marine Museum10-5

To recognize and celebrate the impact of Pax River! Free boath rides, kids activities, arts + crafts, petting zoo, live music + environmental exhibits

FREE event


Bruderfest @ Brüdergarten .

Dachsund Races, live music, German beer, local craft beers, spirits, delicious light fare foods, live entertainment, contests, games.

11 @ Leonardtown Square- Parade of Brewers + dog costume contest.

11am-11pm $5/person


✨Oktoberfest @ NoThymeToCook 11-7

food from Steamers, Live music, Beer related classes throughout the day on our second floor.

4pm Costume Contest for best Bavarian attire.

21+ $15/person, 7-20 $7/person, Under 6 FREE


Sunday


Dinner + Cruise @ St. Clements Island 2-6pm

Guided water tour, dinner at Morris Point Restaraunt, dessert at St. Clements Island Museum

$75/person, $140/couple, register online


Afternoon Cruise @ Leonardtown Wharf 11-2

$35/person register online


Sunset cruise@ Pier 450 4:45-6:45

$35/person, register online 

This Weekend: September 30th, October 1st and 2nd

Rain has canceled most of the regularly scheduled events. Here are some of our favorite indoor spaces.

Grab a glass of award winning wine and listen to live music @ Port of Leonardtown 2-5

See the fossils, boats, fish, and otters @ Calvert Marine Museum from 10-5

Annmarie Gardens has a great indoor space. Enjoy their gallery and kids will love their nature nook and creating art from recycled goods in their art lab

Imaginarium is a great indoor play space for kids. Think giant indoor playground with extra toys! $14/kid, $10/additional sibling

This Weekend: September 23rd, 24th, and 25th

Saturday + Sunday:

St. Mary’s County Fair!!!

Fri + Sat 9am-10pm. Sun 9-7. Ticket prices vary per day


Seasonal Opening of Bowles Farm Corn Maze!

Sat 10-6, Sun 10-5

$15/person, children under 3 are FREE


Saturday Line-Up:

Group Fossil Hunt @ Flag Ponds

10-12, $7/per vehicle


Riverfest @ St. Mary’s State house

Celebrate our waterways with free activities, entertainment, and learning about the environment through informative and hands-on exhibits.

11-4 FREE


Toy Boat Building @ CMM

1pm in outdoor pavilion


Life Journey Writing @ Prince Frederick Library

Incredible experience to be led by an expert through documenting your life experiences.

2-4


Free afternoon live music @ our local wineries

Sip some great wine and enjoy great music at Perigeaux, Running Hare, Port of Leonardtown, Xella


Sunday Spotlight

Artisan Sip & Shop @No Thyme to Cook

11-5. FREE

September 16th, 17th, and 18th

Sat + Sun:

Artsfest @ Annmarie Gardens

No one does festivals like Annmarie Gardens. So much to do, eat, listen to, and local vendors to support. This seriously is a must-attend event.

10-5. $10/person

North beach Film Festival @ various locations + times around North Beach

$15/screening block


Sat:

Coastal Arts Market @ Leonardtown Wharf. 9-3

Pirate Day @ Calvert Marine Museum

Make a pirate flag, build a toy pirate boat, get a pirate tattoo, sing pirate songsand walk the plank! 10-5 $7/person

Live Music @ Running Hare Winery. 12-4

Leonardtown Summer Music Festival @ Port of Leonardtown. 2-5

Amish Outlaw Band @ Tiki Ba. 7 pm


Sun:

SOMD Coffee and Cars @ Laurel Glen Shopping Center. 8-5pm

Sunset Cruises @ Pier 450. 5:15-7:15 $35/person

If you ever have questions about what to do in Southern Maryland or what's happening with the real estate market, send us a message! We love talking about all things Southern Maryland.

Regular Events

There are special events that happen on the first Friday of every month in Leonardtown! There are regularly performances by local music groups, art exhibitions, and holiday celebrations. Businesses stay open late and may offer specials for First Friday customers! Stop by, walk the square, eat good food, and take in the festive atmosphere!

Trivia and Open Mic Nights at St. Inie's Coffee in Lexington Park

St. Inie's continues to foster community through exceptional coffee, personable staff, and regular events like open mic performances by artists such as Dog Army, and trivia nights outside of regular hours! St. Inie's is open from 7AM to 3PM Monday through Saturday, with special events at 6PM!