SOUTHERN MARYLAND — Ready to make the most of your week in Southern Maryland? From waterfront concerts and sunset cruises to kids’ LEGO night, glass blowing, silent discos, and Renaissance flair—there’s something for everyone happening May 23 through May 29. Whether you’re planning a family outing, date night, or solo adventure, Calvert, Charles, and St. Mary’s counties are packed with ways to unwind and explore.
Looking for ways to honor Memorial Day? See our full list of remembrance events across Southern Maryland and beyond.
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CALVERT COUNTY
Bad Art Night at Annmarie on May 23 (5 p.m.), located at Annmarie Sculpture Garden & Art Center, 13470 Dowell Road, Solomons, MD – Adults 21+ are invited for a fun, no-rules evening of outrageous art-making, music, and prizes for the “Best of the Worst.” Cash bar available. $7/person; FREE for members.
George W. Owings, III Stars & Stripes Ceremony & Festival on May 24 (10 a.m., with Family Fun Day from 12 to 2 p.m.), located at Veterans Memorial Park, 8217 Bayside Rd, Chesapeake Beach, MD – This annual Memorial Day weekend event honors military service and celebrates freedom with a patriotic ceremony featuring guest speakers and tributes. The celebration continues at Kellam’s Field with a Family Fun Day including games and activities for all ages. Free admission.
DJ All-In on May 24 (9 p.m. to close), located at Rod ‘N’ Reel Resort: Gaming Building, 4150 Mears Avenue, Chesapeake Beach, MD – Join DJ All-In for a high-energy night of music on the first floor of the Gaming Building. Enjoy tunes, test your luck on pull-tab machines, and grab a drink while you dance the night away. Free admission.
Jordan Davis with opener Dasha – Live in Concert on May 24 (5:30 pm), located at CMM’s Motto Mortgage Preferred and RE/MAX One Waterside Pavilion, 14200 Solomons Island Road S, Solomons, MD – Catch award-winning, multi-platinum artist Jordan Davis live on his Damn Good Time Tour, performing hits like “Buy Dirt” and “Next Thing You Know.” Platinum-certified singer-songwriter Dasha will open the show with her viral hit “Austin.” Tickets required.
Rock the Dock: The NoWhere Men on May 25 (2 p.m.), located at Rod ‘N’ Reel Resort’s Bandshell, 4160 Mears Ave, Chesapeake Beach, MD – Hear classic hits from soul, Motown, funk, and pop legends performed by The NoWhere Men, featuring award-winning musicians and a powerful horn section. Tickets required.
Music on the Water Cruise with Justin Allen on May 25 (6:30 p.m.), departs from Solomons Island, 14443 Solomons Island Rd, Solomons, MD – Enjoy a relaxing evening cruise featuring live music by Justin Allen, set against the backdrop of scenic waterfront views. Perfect for date night or a peaceful solo escape. Tickets required.
Military Appreciation Cruise on May 26 (1 to 3:45 p.m.), located at Solomons Island, 14443 Solomons Island Rd, Solomons, MD – Set sail on a tropical-themed tiki cruise to honor and celebrate our nation’s military service members. Enjoy waterfront views, island vibes, and a complimentary first drink for veterans and active-duty guests. Tickets required.
Dungeons & Drafts – A D&D One-Shot at Mully’s Brewery! on May 28 (6 to 9 p.m.), located at Mully’s Brewery, 141 Schooner Lane, Prince Frederick, MD – Join an epic Dungeons & Dragons one-shot adventure, “Sakura’s Last Bloom,” featuring level 3 characters, miniatures, and experienced Dungeon Masters. Open to all skill levels. $25 per person. Spots are limited; advance ticket purchase recommended.
Rock the Dock: StevieMac (Fleetwood Mac & Stevie Nicks Experience) on May 29 (7 p.m.), located at Rod ‘N’ Reel Resort, 4160 Mears Ave, Chesapeake Beach, MD – Enjoy an immersive tribute to Fleetwood Mac and its legendary members with StevieMac’s theatrical performance featuring authentic costumes, multimedia, and storytelling. Tickets required.
For more Calvert County events, visit the Calvert County Maryland website.
CHARLES COUNTY
George Lynch at Island Music Company on May 23 (5 to 7 p.m.), located at Island Music Company, 403 Charles Street, La Plata, MD – Legendary guitarist George Lynch will host a free music clinic followed by a meet-and-greet session. Don’t miss this opportunity to learn from and meet a rock icon. Free admission.
Town of La Plata Summer Concert Series: Girl Crush on May 23 (7 p.m.), located at La Plata Town Hall Lawn, 305 Queen Anne Street, La Plata, MD – Kick off the summer concert season with a high-energy performance by Girl Crush, bringing country hits and crowd favorites to the heart of town. Bring your lawn chairs, picnic blankets, and friends for a fun, family-friendly night of music. Free admission.
The 4th Annual Southern Maryland Gold Star Legacy Ride on May 24 (9:30 a.m. to 5:30 p.m.), located at American Legion Post 82 – Harry White Wilmer, 6330 Crain Highway, La Plata, MD – The American Legion Riders of Post 82 in La Plata, Maryland, are excited to announce the 4th Annual SoMD Gold Star Legacy Ride on May 24, 2025. This year’s scenic ride through Southern Maryland will conclude with a finalè celebration at Harry White Williams American Legion Post 82, featuring music, food, drinks for sale, raffles, local vendors, and photo opportunities.
Southern Maryland House of Nerf May 2025 Blaster Battle on May 24 (11 a.m. to 5 p.m.), located at Charles County Fairgrounds and Event Center, 8440 Fairground Road, La Plata, MD – Join the Maryland Foam Alliance for an action-packed day of competitive scrimmages and player-versus-player Nerf battles. All skill levels welcome. Tickets required.
Kids Sneaker Ball Paint Party on May 24 (5 to 8 p.m.), located at Paint N Sip, 11110 Mall Circle, Waldorf, MD – Kids are invited to dress up and get creative at this fun sneaker-themed paint party inside the St. Charles Mall. Expect music, painting, and party vibes all evening long. Tickets required.
SPARK! Places of Innovation Exhibit on May 27 (10 a.m. to 6 p.m. ), located at CSM Velocity Center, 4465 Indian Head Hwy, Indian Head, MD – This traveling Smithsonian exhibit highlights how rural communities across America spark creativity, solve problems, and drive innovation through collaboration and ingenuity. Free admission.
All About LEGOs on May 27 (6 to 7 p.m.), located at Somers Community Center, La Plata, MD – Kids ages 6 to 12 can unleash their creativity through LEGO projects, games, and building challenges. Each session features a new theme for imaginative play and collaboration. $12 for residents / $14 for non-residents. Registration required.
For more Charles County events, visit the Charles County Maryland website.
ST. MARY’S COUNTY
SMTMD HomeSpun CoffeeHouse Open Mic on May 23 (7 to 9:30 p.m.), located at Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – Acoustic musicians of all skill levels are welcome to perform their favorite tunes or enjoy a night out listening to some local talent. A keyboard can be made available by prior arrangement. Contact Chris Dudley in advance (ccdudley@rocketmail.com) to sign up as a performer. Admission is $8; children 17 and under (when accompanied by a paying adult) and performers are admitted free of charge.
Summer Splash: Silent Disco on May 23 (5 to 10 p.m.), located at Leonardtown Wharf, 22500 Washington Street, Leonardtown, MD – Grab a headset and dance the night away to your choice of three music streams featuring DJ FMM, DJ TJ, and a request line. Food available from Scratch Mobile Kitchen (5–8 p.m.). Bring a chair if you need a break from the beats. $20 per headset.
Glass Blowing at the Winery on May 24 (3:30 to 5:30 p.m.), located at Port of Leonardtown Winery, 23190 Newtowne Neck Road, Leonardtown, MD – Create your own glass art piece with help from McFadden Art Glass Studio’s mobile team. Choose from a wine glass, vase, ornament, and more. Includes a glass of wine, sangria, or slushie. Projects available for pickup two days later. Tickets required.
RenFest Southern Maryland on May 24 and May 25 (10 a.m. to 8 p.m.), located at Shepherd’s Old Field Market, 22725 Duke Street, Leonardtown, MD – RenFest Southern Maryland is the region’s premiere renaissance faire! Here fantasy, history, and humor transcend both time and realm, welcoming all people and creatures to escape reality and celebrate play. The faire boasts three stages full of music, mischief, and magic, a village of vendors, and feastable food fit for a king. We invite you to spend a weekend immersed in fellowship and fun in the better world of our dreams! Tickets required.
College Sailing Nationals at St. Mary’s College from May 27–30, located at The James P. Muldoon River Center and The Teddy Turner Waterfront, 47498 Trinity Church Rd, Lexington Park, MD – Watch top collegiate teams from across the U.S. compete in the ICSA Open Fleet Race National Championships on the St. Mary’s River. Enjoy four days of thrilling races as teams vie for the national title. FREE for spectators.
500 by 5 Celebration! on May 27, 2025 (10 to 11 a.m.), located at Leonardtown Library, Meeting Rooms 1 & 2, 23630 Hayden Farm Lane, Leonardtown, MD – Celebrate early literacy milestones with a special storytime, crafts, coloring, and a dance party for toddlers and preschoolers. Registration is required for children only. FREE.
Little Explorers: Personal Gardens on May 28 (10 to 11 a.m.), located at Historic St. Mary’s City, 18751 Hogaboom Lane, St. Mary’s City, MD – Preschoolers ages 3–5 and their caregivers are invited for a fun-filled morning of discovery through stories, art, science, and nature. This session’s theme is Personal Gardens. $4 per child general / $3 members; one adult free with child. Full-day museum admission included.
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 23rd
5:00pm – Chris Dean – Greene Turtle Sports Bar – La Plata MD
5:00pm – WIP Acoustic – Greene Turtle Sports Bar – California MD
5:00pm – Dust on the Bottle – Mully’s Brewery – Prince Frederick MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – John Luskey – Happy Harbor Restaurant – Deale MD
5:30pm – Sister Midnight – Running Hare Winery – Prince Frederick MD
5:30pm – Greg Barrick – Dockside Tiki Bar – Colonial Beach VA
5:30pm – David Norris & Stu – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Rayon Walker – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Fresh Pint – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Byron Cottier – The Local – Hollywood MD
6:00pm – Doc Lohn – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Chris Turner – Southern Trail Distillery – Mechanicsville MD
6:00pm – Never 2 Late – Wheel House Beer Garden – North Beach MD
6:00pm – Audra & Johnny – Ruddy Duck Brewery & Grill – Solomons MD
7:00pm – The Reagan Years – The TIKI Bar – Solomons MD
7:00pm – Girl Crush – Town Hall Concert Series – La Plata MD
7:00pm – One Trick Pony – Fitzies Marina & Pub – Leonardtown MD
7:00pm – Todd Murry – Swan Point Country Club – Swan Point MD
7:00pm – The Reagan Years – The TIKI Bar – Solomons MD
8:00pm – Rattlesnake Pete – Toots Bar – Hollywood MD
8:00pm – Mike Mead & Eric Wolf – Phil’s Place – Hughesville MD
8:00pm – Jump (Van Halen tribute) – The Rex Theatre – Leonardtown MD
8:00pm – Myles Deep Band – The Taphouse 1637 – California MD
9:00pm – Last Shot Band – Twisted Bar & Grill – Hollywood MD
Saturday – May 24th
10:00am – Byron Ciotter – Bugeye Grill – Solomons MD
10:00am – RenFest Southern Maryland – Brudergarten – Leonardtown MD
12:00pm – Mark & da Sharks – Running Hare Winery – Prince Frederick MD
12:30pm – Nate Yelding – Two Lions Vineyards – Upper Marlboro MD
1:30pm – Sons of Pirates – The TIKI Bar – Solomons MD
2:00pm – High Energy Group – Robin Hill Farm – Brandywine MD
2:00pm – David Sparrow – Port of Leonardtown Winery – Leonardtown MD
2:30pm – Nightcap – Farm Brew Live! – Manassas VA
3:00pm – Midnight Sunsets – The Boathouse @ Anchored Inn – Deale MD
4:00pm – Justin Myles & Prophessor – Dennis Point Marina – Drayden MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – The Highway Ramblers – Cryer’s Back Road Inn – Compton MD
5:00pm – Mike Mead & Eric Wolf – Running Hare – Prince Frederick MD
6:00pm – Fat Whiskey – Happy Harbor Restaurant – Deale MD
6:00pm – Red Bullitt – Traders Seafood & Ale – Chesapeake Beach MD
6:00pm – Justin Allen – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Basement Snakes – Wheel House Beer Garden – North Beach MD
6:00pm – Smoke Signals – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Chris Dean – The Local – Hollywood MD
6:00pm – Greg Barrick – Southern Trail Distillery – Mechanicsville MD
6:30pm – Shane Graham – Bugeye Grill – Solomons MD
7:00pm – Timothy Ridgell – Pax River Ale House – Lexington Park MD
7:00pm – Blair Rich Band – The Potomac Gardens – Coltons Point MD
7:00pm – Funkzilla – Blue Fish Pub – Solomons MD
7:00pm – Jordan Davis / Dasha – Calvert Marine Museum – Solomons MD
7:00pm – Mike Trujillo – The Brass Tap – California MD
7:30pm – The Amish Outlaws – The TIKI Bar – Solomons MD
8:00pm – Reggie Rice Comedy & Magic – Taphouse 1637 – California MD
8:00pm – The Rise Band & Show – Coast 2 Coast – Solomons MD
8:00pm – Monkey Business – Huntt’s Tavern – Pomfret MD
8:00pm – Social – Toots Bar – Hollywood MD
8:00pm – Concerts on the Creek – Sunset Creek @ Vera’s – Lusby MD
————- Deadbeat Holiday, The Young Swains, Vivid Vertigo, SMIBS –
8:30pm – 4th Wall Break- Ollie’s Bar & Grill – La Plata MD
9:00pm – Lookout – Buckets Bar & Grill – Lusby MD
9:00pm – Buffalo Velcro – Twisted Bar & Grill – Hollywood MD
Sunday – May 25th
12:00pm – Midnight Sunsets – The TIKI Bar – Solomons MD
1:00pm – Run Catch Rain – Running Hare Winery – Prince Frederick MD
1:00pm – One Way Acoustic – Twisted Bar & Grill – Hollywood MD
2:00pm – Never 2 Late – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Jack Allen – Southern Trail Distillery – Mechanicsville MD
2:00pm – Richard Wagner – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Shari Flowers-Sweeney – Robin Hill Farm – Brandywine MD
2:00pm – Sold Separately – Wharf 38 – Deale MD
2:00pm – John Luskey – Pirates Cove Dock Bar – Galesville MD
3:00pm – Ryan Forrester – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Peter James – Happy Harbor Restaurant – Deale MD
3:00pm – James Cornett – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Mike Mead & Eric Wolf – Traders Seafood – Chesapeake Beach MD
3:00pm – Justin Myles – The Pier – Solomons MD
3:00pm – Greg Barrick – The Scuttlebutt – Cobb Island MD
3:00pm – Maryland Monroe – Potomac Speedway – Budds Creek MD
5:00pm – One Trick Pony – Blue Fish Pub – Solomons MD
5:00pm – Funkzilla – Bugeye Grill – Solomons MD
5:00pm – Thunderball – The TIKI Bar – Solomons MD
6:00pm – Levi Stephens – Wheel House Beer Garden – North Beach MD
8:00pm – Dagenhart – Toots Bar – Hollywood MD
Monday – May 26th – Memorial Day
1:00pm – The Bootleggers – Pier 450 Restaurant – Ridge MD
1:00pm – Folk Salad – Port of Leonardtown Winery – Leonardtown MD
1:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
2:00pm – Sick Setlists in the Sand – Seabreeze Bar – Mechanicsville MD
————- Changing Scene, shallowDeep, Intentionally Blank, Mike Trujillo
2:00pm – Nightcap – The Boathouse @ Anchored Inn – Deale MD
2:00pm – Peter James – Wharf 38 – Deale MD
3:00pm – Doc Lohn – Pirates Cove Dock Bar – Galesville MD
3:00pm – Whiskey Brothers – Happy Harbor Restaurant – Deale MD
3:00pm – Byron Ciotter – Traders Seafood & Ale – Chesapeake Beach MD
3:00pm – Chris Dean – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Mariah Jean – The Scuttlebutt – Cobb Island MD
Tuesday – May 27th
5:00pm – Catey Peters – Heritage 485 – Prince Frederick MD
6:30pm – Greg Barrick – The Tavern – Saint Leonard MD
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – May 28th
5:00pm – 3 of a Kind – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Billy Breslin – The Pier – Solomons MD
6:00pm – Mike Heuer – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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