Things To Do In Southern Maryland 22 Through May 28, 2026

SOUTHERN MARYLAND — Memorial Day weekend is packed with things to do across Calvert, Charles and St. Mary’s counties — from Renaissance fairs and veteran rides to baby goat yoga, live music and ceramic painting nights. Whether you are looking for family fun, live entertainment or a reason to get outside and explore Southern Maryland, there is no shortage of ways to make the most of the long weekend.

As you enjoy the holiday weekend, pause at 3 p.m. Monday for the National Moment of Remembrance, a one-minute tribute honoring those who died while serving in the U.S. military. U.S. flags are flown at half-staff until noon and returned to full staff afterward.

Rain is possible during parts of the holiday weekend, so check with venues before heading out. Start planning with our event calendar and our top picks below.

To have your upcoming event featured, please enter your event information on our Events Calendar.

Credit: Arlington National Cemetery | The 157th National Memorial Day Observance at Arlington National Cemetery 2025

THINGS TO DO IN CALVERT COUNTY

☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.

Bad Art Night: Adults-Only Fun! on May 22 (5 p.m.), at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Rd, Solomons, MD – An adults-only night of unconventional, unorthodox art-making; guests browse gallery works for inspiration, then create their own masterpieces using supplied materials. Finished artwork goes on display and attendees vote for “The Best of the Worst,” with prizes awarded. Admission required.

Ceramic Paint Night at WhataBoba Lusby on May 22 (6–8 p.m.), at WhataBoba Lusby, 232 Town Square Dr, Lusby, MD — Paint a ceramic trinket box or gnome ring holder with acrylic paints; finished pieces are glazed and ready to take home the same night; limited to 10 participants and no walk-ins permitted. Tickets required.

iNaturalist — North Beach Nature Center on May 23 (10 a.m.–noon), at Bayside History Museum, 4025 4th St., North Beach, MD — Naturalist-led presentation on the iNaturalist app with one-on-one support to help participants explore and identify local plants, birds and insects using their smartphones. Free admission.

Beyond the Displays: Artifact Stories on May 24 (1:30–2:30 p.m.), at Calvert Marine Museum, 14200 Solomons Island Road S, Solomons, MD — Museum educator Lori leads an exploration of the museum’s artifacts uncovering their origins and significance, including how World War II shaped Solomons and hidden details in the museum murals. Included with museum admission.

National Moment of Remembrance on May 25 (3 p.m.), wherever you are — Pause for one minute at 3 p.m. to honor those who died in service to the nation, as designated by Congress in 2000; flags should be raised to full staff at sunrise, lowered to half-staff until noon, then raised again for the remainder of the day.

Sketching for Beginners on May 26 (1–3 p.m.), at m.), at Kocen Arts Center, 22 Duke St., Prince Frederick, MD — Beginner sketching class covering the fundamentals of drawing, crafting a value tool to take home and exploring the interplay of light and value in artwork. Registration required.

I S.T.E.M. for Ice Cream on May 27 (10–11 a.m.), at Mt. Hope Community Center, Calvert County, MD — S.T.E.M. program for children ages 2–5 exploring the chemistry behind freezing as participants shake, mix and experiment their way to a delicious treat. Free. Preregistration required.

Laughs & Lagers on May 27 (3–9 p.m.), at Mully’s Taproom, 141 Schooner Ln, Prince Frederick, MD — Tell your best joke to taproom manager Kelsey and if you make him laugh, he’ll buy you a pint; dad jokes encouraged. Free admission.

Reading Buddies — Teen Buddy on May 27 (6:30–7:30 p.m.), at Calvert Library Prince Frederick, Prince Frederick, MD — Elementary-aged children read aloud and do activities with teen volunteers in a welcoming Teen Zone setting; teens earn one service learning hour for participating; bring a favorite book or borrow one on site. Free. Registration required.

Yoga on the Terrace on May 28 (6:30–7:30 p.m.), at Twin Beaches Branch — Terrace, 4100 5th St., Chesapeake Beach, MD — Gentle flow yoga class for all levels on the terrace overlooking the Bay, led by instructor Amy Melcher; bring a yoga mat and water; class canceled in inclement weather. Free. Registration required.

Trivia and Karaoke Night at Anthony’s on May 28 (7–11:30 p.m.), at Anthony’s Bar and Grill, 10379 MD-4, Dunkirk, MD — Five rounds of trivia kick off at 7 p.m. followed by karaoke; team or singles play with prizes awarded nightly; space is limited so arrive early. Free admission.

For more Calvert County events, visit the Calvert County Maryland website.

THINGS TO DO IN CHARLES COUNTY

☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.

Baby Goat Yoga on May 22 (6–8 p.m.), at Idlewilde Farm, Idlewilde Farm Pl, La Plata, MD — Outdoor yoga session with Sonja from Zentral Station followed by baby goat feeding and petting 7–8 p.m. Tickets required.

BOO Bingo at Scary Strokes on May 22 (7 p.m.), at Scary Strokes, 2960 Technology Place, Suite 106, Waldorf, MD — Family-friendly bingo night with live number calling, free bingo cards and prizes including free passes, arcade cards and a $50 gift card; first come, first served with limited seating. Free admission.

Friday Night Summer Concerts on May 22 (7–10 p.m.), at La Plata Town Hall Lawn, 305 Queen Anne St., La Plata, MD — The Town of La Plata kicks off its Summer Concert Series with Girl Crush performing high-energy Pop Rock and Top 40 hits. Free admission.

Bird Walk at Piscataway MOS Sanctuary on May 23 (7:30–10:30 a.m.), at Piscataway MOS Sanctuary, 14300 Hardy Tavern Drive, Accokeek, MD — Free guided bird walk led by a Maryland Ornithological Society guide, open to all ages and experience levels; loaner binoculars available upon request. Free. Registration required.

Star Wars: Attack of the Clones — Scenario Event on May 23 (8 a.m.), at Southern Maryland Paintball, 11272 Edge Hill Rd, Newburg, MD — Real-life Star Wars paintball scenario event with massive missions and a giant battlefield; choose your side as the Republic (Clone Army) or the Separatists (Droid Army). Tickets required.

5th Annual Southern Maryland Gold Star Legacy Ride on May 23 (9:30 a.m.), at American Legion Riders Chapter 82, 6330 Crain Hwy, La Plata, MD — Scenic motorcycle ride through Southern Maryland hosted by the American Legion Riders of Harry White Wilmer Post 82 honoring veterans and raising funds for veteran-support organizations; includes free breakfast, free lunch, music, raffles and a $250 Best Hand Poker Run. Tickets required.

Explore. Learn. Thrive. Pop-Up Event on May 23 (11 a.m.–2 p.m.), at 8001 Sheriff Road, Landover, MD — Kickoff event for Prince George’s County Health Department’s community outreach campaign connecting residents with public health resources, programs and department staff; learn about upcoming district-level pop-up events countywide. Free admission.

Live Birds of Prey on May 23 (11 a.m.–2 p.m.), at Wild Birds Unlimited, 58 Shining Willow Way, La Plata, MD — Mike Callahan from Nanjemoy Creek Environmental Center shares live birds of prey and his knowledge of these remarkable animals at the store. Free admission.

Line Dance at Graces Event Center on May 23 (7–11 p.m.), at Graces Event Center, 4045 Renner Rd, Waldorf, MD — Spring line dancing party featuring DJ Double O Soul with plenty of dancing and a good time with friends. Tickets required.

80s Dress Up & Dance Party on May 23 (7 p.m.), at The Scuttlebutt, 12320 Cobb Island Rd, Cobb Island, MD — Dress up in your best 80s style for a night of dancing with a cash prize for best dressed. Free admission.

Moonbounce Monday — Chick-fil-A & Play on May 25 (1–4 p.m.), at My Gym Waldorf, 1148 Smallwood Dr W, Waldorf, MD — Drop-off event for kids featuring a 5-count chicken nugget Kids Meal with fruit cup and juice pouch, sports relay, and a STEAM craft building a mini foosball table. Tickets required.

Jazz Night at The Charles on May 27 (7–9 p.m.), at The Charles Restaurant and Bar, 417 E. Charles St., La Plata, MD — Weekly live jazz night featuring Ricardo L. Abbott and the NBAF Quartet in an intimate setting with dining and cocktails in downtown La Plata. Free admission.

For more Charles County events, visit the Charles County Maryland website.

THINGS TO DO IN ST. MARY’S COUNTY

☀️ See our Summer Camp Guide for Southern Maryland here.
🍦 See where Kids Eat Free in Southern Maryland here.

St. Mary’s County Memorial Day Adoption Event on May 22–24 at St. Mary’s County Animal Adoption & Resource Center, 22975 Franklin Delano Roosevelt Blvd., California, MD — Fee-waived adoption event honoring the memory of beloved pets while helping shelter animals find new homes; standard application, screening and background check process applies. Free admission.

Trivia Night at Corteau Vineyards on May 22 (6–8 p.m.), at Corteau Vineyards, 38713 Golden Beach Rd, Mechanicsville, MD — Teams of up to six compete for gift card prizes; first place wins a $25 Corteau gift card, second place wins a $15 gift card. Free admission.

RenFest Southern Maryland on May 23–24 (10 a.m.–7 p.m.), at Brudergarten Beer Garden, 22725 Duke St., Leonardtown, MD — Two-day Renaissance faire featuring four stages of music, mischief and magic, a village of vendors and festival food; all ages and creatures welcome to escape reality and celebrate play. Tickets required.

Maryland Dove Public Sail on May 23 (10 a.m. and 1 p.m.), at Historic St. Mary’s City, 18751 Hogaboom Lane, St. Mary’s City, MD – Step aboard the Maryland Dove for a relaxed two-hour public sail on the St. Mary’s River aboard this beautifully crafted wooden vessel inspired by the original Dove of 1634. Ages 5 and up. Rain date May 30. Registration required.

Breakfast with the Animals on May 23 (10:30–11:30 a.m.), at Historic St. Mary’s City, 18751 Hogaboom Lane, St. Mary’s City, MD – Start the morning with a behind-the-scenes look at life on the Godiah Spray Tobacco Plantation; help feed the cows, chickens and pigs alongside plantation staff, learn about animal care and enjoy a guided tour of the site as the museum opens for the day. All ages; children 2 and under free. Space is limited. Registration required.

Southern Maryland Trivia Night on May 23 (doors open 5:30 p.m., trivia begins 6–8 p.m.), at The Potomac Gardens, 20254 Colton Point Rd, Coltons Point, MD — A night of Southern Maryland trivia hosted by St. Mary’s County Museum Division and Potomac Gardens; teams of five or fewer compete for prizes; bar and Farm.Fork.Soul food truck available; designated drivers receive free non-alcoholic beverages; donations welcome to support the museums. Free admission.

Rex Theatre Memorial Day Party on May 23 (8:30 p.m.), at The Rex Theatre, 22695 Washington St., Leonardtown, MD — Memorial Day weekend party featuring DJ Sammy Samz, Surfsides cocktails, and limited edition drinks, cups and punch buckets; sponsored by Guy Distributing. Tickets required.

Glass Blowing with McFadden Glass on May 24 (11:30 a.m.), at Port of Leonardtown Winery, 23190 Newtowne Neck Rd, Leonardtown, MD — Hands-on glass blowing experience in small hourly groups with McFadden Glass; create a custom glass piece of your choice with a glass of wine included; all ages welcome; spots limited. Tickets required.

Memorial Day Bourbon Tasting on May 25 (1–3 p.m.), at Tobacco Barn Distillery, Hollywood, MD — Special Memorial Day tasting honoring military personnel featuring the distillery’s exclusive D-Day Bourbon, the only bourbon aged airborne over Normandy. Tickets required.

Beginner Pickleball with Lucinda on May 26 (9–11 a.m.), at Garvey Senior Activity Center, 23630 Hayden Farm Ln, Leonardtown, MD — Free beginner class led by experienced player and volunteer Lucinda covering rules, tips and hands-on practice with loaner paddles and balls; wear comfortable clothes and tennis shoes and bring water. Advanced registration required.

NHRA Driver Meet & Greet at The Barns at New Market on May 28 (5 p.m.), at The Barns at New Market, 29133 Thompson Corner Road, Mechanicsville, MD — Exclusive meet and greet with NHRA-qualified drivers ahead of the inaugural NHRA Potomac Nationals with live music from Funkzilla, food, local wine, and a classic car show. Free admission.

For more St. Mary’s County events, check out the Visit St. Mary’s MD website.

SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS

Friday – May 22nd

3:00pm – Greg Barrick – Dockside Tiki Bar – Colonial Beach MD

3:45pm – Funkzilla – Big Kahuna Cruises – Solomons MD

5:00pm – Chris Dean – Greene Turtle Sports Bar – California MD

5:00pm – Mike Mead – Greene Turtle Sports Bar – La Plata MD

5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD

5:00pm – Jack Allen – Mully’s Brewery – Prince Frederick MD

5:00PM – Amish Outlaws – The TIKI Bar – Solomons MD

6:00pm – Karlee Ryce – The Local – Hollywood MD

6:00pm – 4th Wall Break – Seabreeze Tiki Bar – Mechanicsville MD

6:00pm – John Luskey – Stoney’s Clarkes Landing – Hollywood MD

6:00pm – Goodbye Vienna – Port Tobacco Restaurant – Port Tobacco MD

6:00pm – Amish Outlaws – The TIKI Bar – Solomons MD

6:00pm – Never 2 Late – Wheel House Beer Garden – North Beach MD

6:00pm – Wes Ryce – Dockside Restaurant & Sports Bar – Deale MD

6:00pm – Rob Blake – Southern Trail Distillery – Mechanicsville MD

6:30pm – Singer Songwriter Spotlight – Bugeye Grill – Solomons MD

6:30pm – Byron Ciotter – Ruddy Duck Brewery & Grill – Solomons MD

6:30pm – Mariah Jean – Trueman Vineyards & Winery – Aquasco MD

7:00pm – Girl Crush – Town Hall Concert Series – La Plata MD

7:00pm – Pete Best – Pirates Cove Dock Bar – Galesville MD

7:00pm – Smoke Signals – Swan Point Country Club – Swan Point MD

7:30pm – Shaun Gomban – Drift Inn Crab House – Mechanicsville MD

8:00pm – Nightcap – Olde Town Pub – Leonardtown MD

8:00pm – South Creek – Toots Bar – Hollywood MD

9:00pm – Myles Deep Band – Blackwall Hitch – Annapolis MD

Saturday – May 23rd

10:00an – Ricky McNutt – Community Event @ Park & Ride – Golden Beach MD

11:00am – Copper Pennies – Blueberry Fest @ Barefoot Farms – Avenue MD

12:00pm – Boogie Blues Explosion – The Bargain Barn – Hughesville MD

12:00pm – Greg Floberg – Running Hare Winery – Prince Frederick MD

1:00am – Ty Burkhardt – Xella Winery – Mechanicsville MD

2:00pm – Gloria’s Imagination Band – POL Winery – Leonardtown MD

2:00pm – High Energy Group – Robin Hill Vineyards – Brandywine MD

2:00pm – Mike Mallick – JaneMark Winery – Brandywine MD

2:00pm – Alan Prather – Corteau Vineyards – Mechanicsville MD

2:00pm – Fight Cancer Fest – Twisted Bar & Grill – Hollywood MD

———- Midnight Sunsets, HydraFX, Copper Pennies & Funkzilla –

2:30pm – Nightcap – NOVA Live – Manassas VA

3:00pm – Vicki Roberts Band – Skippers Pier – Deale MD

3:00pm – Kurt Gibbons – Pirates Cove Dock Bar – Galesville MD

3:00pm – Fess Up – The Boathouse @ Anchored Inn – Deale MD

3:00am – Callsine – Blueberry Fest @ Barefoot Farms – Avenue MD

5:00pm – Dakota Moss – Green Door Tavern – Park Hall MD

5:00pm – Mike Heuer – Dennis Point Marina & Campground – Drayden Md

5:00pm – John Luskey – Running Hare Winery – Prince Frederick MD

5:00pm – David Norris & The Bad Examples – . Marina – Tall Timbers MD

6:00am – South Creek – Southern Trail Distillery – Mechanicsville MD

6:00pm – Liquid A – The TIKI Bar – Solomons MD

6:00pm – Myles Deep Band – Wheelhouse Beer Garden – North Beach MD

6:00pm – John Hayward – Dockside Restaurant & Sports Bar – Deale MD

6:00pm – Thunderball – Port Tobacco Restaurant – Port Tobacco MD

6:00pm – Hat Trick Band – Blue Fish Pub – Solomons MD

6:30pm – Monkey Business – Bugeye Grill – Solomons MD

7:00pm – Mike Mallick – Neptune’s Seafood Pub – North Beach MD

7:00pm – Stephen Henson – Pirates Cove Dock Bar – Galesville MD

7:00pm – Shane Graham – The Brass Tap – California MD

8:00pm – Top Dead Center – Buckets Bar & Grill – Lusby MD

8:30pm – Buff Huskey – Green Door Tavern – Park Hall MD

9:00pm – Winston – The Taphouse 1637 – California MD

9:00pm – Social – Apehangers Bar & Grill – Bel Alton MD

11:30pm – South Creek – Green Door Tavern – Park Hall MD

Sunday – May 24th

12:00pm – Funkzilla – Amer. Legion Special Olympics Pig Roast – Lusby MD

1:00pm – Fran Scuderi – Running Hare Winery – Prince Frederick MD

2:00pm – Midnight Sunsets – Seabreeze Tiki Bar – Mechanicsville MD

2:00pm – One Foot in the Groove – POL Winery – Leonardtown MD

2:00pm – Chris Dean – Robin Hill Farm & Vineyards – Brandywine MD

2:00pm – Steve Potter Band – Apehangers Bar & Grill – Bel Alton MD

2:00pm – Scoglio Duo – Pirates Cove Dock Bar – Galesville MD

2:00pm – Sold Seperately – Wharf 38 – Deale MD

2:00pm – Pete Best – Skipper’s Pier – Deale MD

2:00pm – Motorboat Co – Southern Trail Distillery – Mechanicsville MD

3:00pm – American Darling – The Boathouse @ Anchored Inn – Deale MD

3:00pm – Joe Cox – Toots Bar – Hollywood MD

3:00pm – Monkey Business – Stoney’s Clarkes Landing – Hollywood MD

3:00pm – Jambros – The Pier River Bar – Solomons MD

3:00pm – Water’s Edge Band – Port Tobacco Restaurant – Port Tobacco MD

3:00pm – Greg Barrick – Dockside Restaurant & Sports Bar – Deale MD

5:00pm – The Reagan Years – The TIKI Bar – Solomons MD

5:00pm – The Nighthawks – Fitzies Restaurant & Pub – Leonardtown MD

6:00pm – Faith & The Faithful – Pirates Cove Dock Bar – Galesville MD

6:00pm – I & I Riddim – Wheel House Beer Garden – North Beach MD

6:00pm – The Prophessor – Bugeye Grill – Solomons MD

Monday – May 25th – Memorial Day

1:00pm – The Bootleggers – Pier 450 Restaurant – Ridge MD

2:00pm – Doc Lohn – Pirates Cove Dock Bar – Galesville MD

2:00pm – Jeremy Robinson – Traders Seafood & Ale – Chesapeake Beach MD

2:00pm – Patrick Ward – Port of Leonardtown Winery – Leonardtown MD

2:00pm – Girl Crush Acoustic- The Boathouse @ Anchored Inn – Deale MD

2:00pm – Michael Ferro & Friends – Wharf 38 – Deale MD

2:00pm – The Hometown Band – Port Tobacco Restaurant – Port Tobacco MD

2:00pm – About Last Night – The TIKI Bar – Solomons MD ????

2:00pm – Set Lists in the Sand – Seabreeze Tiki Bar – Mechanicsville MD

——— Others May Fall, shallowDeep & KarOshA –

3:00pm – Vicki Roberts Band – Dockside Restaurant & Sports Bar – Deale MD

3:00pm – Whiskey Brothers – Happy Harbor Restaurant – Deale MD

Tuesday – May 26th

5:00pm – Jambros – Heritage 485 – Prince Frederick MD

6:00pm – River Rock Band – Apehangers Bar & Grill – Bel Alton MD

6:30pm – Greg Barrick – The Tavern – Saint Leonard MD

7:00pm – Open Mic w/Derek Norris – Twisted Bar & Grill – Hollywood MD

Wednesday – May 27th

12:00pm – Hump Day Band – Cryer’s Back Road Inn – Leonardtown MD

4:30pm – Run Catch Rain – No Thyme To Cook – Solomons MD

5:00pm – Pete Best – Ketch 22 Restaurant – North Beach MD

5:00pm – Ryan Webster – The Boathouse @ Anchored Inn – Deale MD

5:00pm – Shaun Gomban – Trifecta Restaurant – Solomons MD

6:00pm – Catey Peters – Pirates Cove Dock Bar – Galesville MD

6:00pm – Mike Heuer – Brick Wood Fired Bistro – Prince Frederick MD

6:30pm – Comedy Open Mic – Twisted Bar & Grill – Hollywood MD

7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD

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