SOUTHERN MARYLAND — There’s no shortage of things to do in Southern Maryland this week, with events popping up across Calvert, Charles, and St. Mary’s counties. Whether wandering through poppy fields in Chaptico, admiring vintage cars in Leonardtown, or stepping back in time at the Southern Maryland Heritage Festival, the region is packed with ways to enjoy the season. Families can also look forward to hands-on kids’ workshops, museum nights, and outdoor fun happening all weekend long.
To have your upcoming event featured, please enter your event information on our Events Calendar.
CALVERT COUNTY
Mom & Me LEGO Night on May 16 (5 to 7 p.m.), located at the Imaginarium – Enjoy an evening of pizza, juice/water, LEGO challenges, LEGO bingo, a LEGO flower craft, and a special photo opportunity with Mom by Flutter By Photography. $50 per family
DJ J-Spin on May 16 (9 p.m. to close), located at Rod ‘N’ Reel Resort: Gaming Building, 4150 Mears Avenue, Chesapeake Beach, MD – Catch DJ J-Spin live on the first floor of the Gaming Building for a night of non-stop music, pull-tab gaming, drinks, and dancing. Free admission.
Night at the Museum for Friends with Disabilities on May 16 (5 p.m.), located at Calvert Marine Museum, 14150 Solomons Island Road, Solomons, MD – Families, friends, and caregivers are invited to a special after-hours evening designed for guests with disabilities. Enjoy exhibits, live animal encounters, lighthouse tours, a calming room, and a cruise on the Wm. B. Tennison (at 5:00, 5:45, or 6:30 p.m.). FREE.
Wine and Line Dancing – May 16 (6 to 10 p.m.), located at Running Hare Vineyard, 150 Adelina Road, Prince Frederick, MD – Join instructor Carole Clark of Dancing by the Bay for an evening of fun for dancers of all experience levels. This activity will be held indoors in the Tuscan Villa. Wine and local craft beer will be available for purchase. $12 per person.
Public Archaeology Day on May 17 (Various Times), located at 10515 Mackall Road, Saint Leonard, MD – Enjoy a full day of outdoor fun and historical exploration at Jefferson Patterson Park & Museum. Start with Patterson House Serenity Flow and Garden Tour (8 to 10 a.m.), followed by Public Archaeology (9 a.m. to 3 p.m.), where participants can dig for artifacts and learn archaeological techniques. Village Days (10 a.m. to 3 p.m.) offers hands-on demonstrations and living history activities. FREE.
HIPPY Calvert Community Baby Shower on May 17 (9:30 a.m. to 12 p.m.), located at Calvert Library Prince Frederick, 850 Costley Way, Prince Frederick, MD – Expecting and new parents are invited to attend a free community baby shower sponsored by HIPPY/Healthy Families/PAT and the Calvert County Health Department. Enjoy resources, giveaways, and support from local organizations. FREE.
Big Bingo Game on May 18 (11 a.m. to 5 p.m.), located at Rod ‘N’ Reel Resort, 4150 Mears Avenue, Chesapeake Beach, MD – Don’t miss a full day of bingo fun, prizes, and excitement! Entry is $40, with tickets available at the door. Pre-order by May 17 to receive a $10 CBQ meal voucher. Tickets required.
Rock the Dock: Earth, Wind & Fire Tribute on May 22 (7 p.m.), located at Rod ‘N’ Reel Resort’s Bandshell, 4160 Mears Avenue, Chesapeake Beach, MD – Enjoy a high-energy performance celebrating five decades of Earth, Wind & Fire hits with this explosive tribute show on the waterfront. Tickets required.
For more Calvert County events, visit the Calvert County Maryland website.
CHARLES COUNTY
Lowe’s Kids Workshops– Spinning Trinket Box on May 17 (10 a.m. to 1 p.m.), located at Lowe’s Home Improvement, 2525 Crain Highway, Waldorf, MD – Children ages 4 and up are invited to build a Spinning Trinket Box during this free, hands-on DIY workshop. Each participant receives a workshop kit, apron, and commemorative badge. Registration required. FREE.
Potomac River Cleanup at Oxon Cove Park on May 17 (9 a.m.), located at Oxon Cove Park, 6411 Oxon Hill Rd, Oxon Hill, MD – Help protect the Potomac River by joining Potomac Conservancy for a 50-person trash cleanup. All supplies provided, but participants are encouraged to bring their own. Registration required. FREE.
SPARK! Places of Innovation Exhibit from May 17 through June 29 (8 a.m. to 5 p.m. daily), located at the CSM Velocity Center, 4465 Indian Head Hwy, Indian Head, MD – This Smithsonian traveling exhibit explores how innovation thrives in rural communities. Learn how small towns across America are meeting challenges, launching inventions, and creating positive change. FREE.
Dimensions of Black Women’s Health on May 17 (10 a.m. to 1 p.m.), located at Westlake High School (cafeteria), 3300 Middletown Road, Waldorf, MD – Presented by Alpha Kappa Alpha Sorority, Inc.® Nu Zeta Omega Chapter in partnership with Ivy and Pearls of Southern MD Community Charities, Inc. This empowering health event will explore critical issues affecting Black women’s wellness. FREE.
Huggy Lowdown & Friends Featuring HBO & BET’s Chris “The Mayor” Thomas on May 17 (7 to 8:30 p.m.), located at Hilton Garden Inn Waldorf, 10385 O’Donnell Place, Waldorf, MD – Don’t miss comedian Chris “The Mayor” Thomas from BET and HBO as part of the Pop-Up Comedy Festival, featuring acts from Shaq’s Showtime Comedy Special. TICKETS REQUIRED via Eventbrite or AllEvents.
The Hangover Brunch on May 18 (1 to 7 p.m.), located at Shark Bar and Seafood House, 2056 Robert S. Crain Hwy, Waldorf, MD – Enjoy a lively Sunday brunch experience with food, drinks, and entertainment hosted by Shark Bar Live. TICKETS REQUIRED.
Junior Ranger Day on May 18 (3:00 p.m.), located at the Maryland Veterans Museum at Patriot Park, La Plata, MD – Children are invited to participate in a fun and educational afternoon hosted in partnership with the National Park Service and DAR. Attendees will have the chance to earn a Junior Ranger Badge for the Washington Rochambeau Revolutionary Route. FREE.
CCYO Spring Concert on May 18 (3 to 5 p.m.), located at Thomas Stone High School, 3785 Leonardtown Rd, Waldorf, MD – Enjoy a free spring performance from the Charles County Youth Orchestra featuring all four ensembles: Prelude Strings, Encore Strings, Encore Band, and the full orchestra. The program includes works by Beethoven, Mozart, Vivaldi, and more. FREE.
Youth Empowerment Workshop: Voices Matter on May 19 (3 to 5 p.m.), located at Phoenix International School of the Arts (PISOTA), 95 Catalpa Drive, La Plata, MD – Hosted by Stella’s Girls, this free workshop for youth ages 12–17 aims to build leadership and advocacy skills through hands-on activities. Participants will explore language access, create civic engagement projects, and earn two Student Service Learning (SSL) hours. Registration is free and includes snacks and supplies. Register here. FREE.
For more Charles County events, visit the Charles County Maryland website.
ST. MARY’S COUNTY
SoMD Blooms Poppy Fest on May 16–18 (Friday, 5 to 9 p.m.; Saturday, 11 a.m. to 5 p.m.; Sunday, 12 to 4 p.m.), located at Goldpetal Farms, 37254 Manor Road, Chaptico, MD – Follow the yellow brick road through poppy fields and themed attractions including a 21+ evening, family fun day, and Armed Forces Appreciation Day with free admission for military families. Food trucks, games, and live entertainment all weekend. TICKETS REQUIRED.
Dungeons & Drafts – A D&D One-Shot at Brudergarten on May 20 (6 to 9 p.m.), located at Brudergarten, 22725 Duke Street, Leonardtown, MD – Join a one-night-only tabletop quest guided by experienced Dungeon Masters. Includes a Level 3 one-shot adventure, pre-made characters, and miniatures for an immersive experience. All levels welcome. $25 per person. Advance registration recommended.
Free Museum Admission for Military on Armed Forces Day on May 18 (10 a.m. to 5 p.m.), at St. Clement’s Island Museum and Piney Point Lighthouse Museum, St. Mary’s County – Active and retired military (with valid ID) receive FREE admission to both museums in honor of Armed Forces Day. Regular admission rates apply to other guests. Water taxi rides to St. Clement’s Island are $7 per person for all visitors. The Old Jail Museum also offers free admission to all year-round. FREE FOR MILITARY; REGULAR ADMISSION FOR OTHERS.
Spring Book Sale: Friends of the St. Mary’s County Library on May 16–18, located at the St. Mary’s County Fairgrounds, 42455 Fairgrounds Rd, Leonardtown, MD – Browse thousands of used books including fiction, nonfiction, young adult, children’s books, media, and rare finds. Friday, May 16 is exclusive to Friends of the Library members (sign up online or at the door). Saturday and Sunday are open to the public, with Sunday offering “Bargain Bag” day deals. Free parking is available.
Photo Scavenger Hunt on May 16–18, located in Downtown Leonardtown, Washington Street, Leonardtown, MD – Capture themed spring photos throughout town for a chance to win prizes and be featured in the St. Mary’s County Times and by the St. Mary’s County Arts Council. Open to all ages. FREE.
Lowe’s Kids Workshops– Spinning Trinket Box on May 17 (10 a.m. to 1 p.m.), located at Lowe’s Home Improvement, 45101 First Colony Way, California, MD– Children ages 4 and up are invited to build a Spinning Trinket Box during this free, hands-on DIY workshop. Each participant receives a workshop kit, apron, and commemorative badge. Registration required. FREE.
Southern Maryland Heritage Festival taking place May 17 and May 18 (11 a.m. to 5 p.m.), located at Historic Sotterley, 44300 Sotterley Lane, Hollywood, MD – Historic Sotterley is excited to host the 2nd Southern Maryland Heritage Festival. The two-day festival will be a celebration of Southern Maryland food, culture, history and the people that make it unique. While exploring the site, guests will be able to tour and learn about the shared realities that have shaped our region and country, shop local with artisan vendors, sample local and traditional food, wine and beer, learn from exhibits and demonstrations, and listen to a range of country, rock, gospel and jazz at various stages. The event will be family-friendly with a dedicated kids’ area for demonstration and play. Tickets required.
Spring Fling Car Show & Running of the Balls on May 18 (8 a.m. to 4 p.m.), located at Leonardtown Square, 22670 Washington St, Leonardtown, MD – Enjoy a day of classic cars, trucks, and motorcycles at the annual Spring Fling hosted by St. Mary’s Rod & Classic Car Club. Featuring music, food, raffles, prizes, and the return of the crowd-favorite Running of the Balls race. Trophies will be awarded to the top 60 entries, with dash plaques for the first 250 vehicles. $5 spectator fee; proceeds benefit Hospice of St. Mary’s and local nonprofits.
Strawberry Festival at Christ Church Chaptico Parish Hall on May 18 (12:30 to 4 p.m.), located at Christ Episcopal Church Chaptico Parish Hall, 37497 Zach Fowler Rd, Chaptico, MD – Enjoy a day of old-fashioned fun featuring strawberry shortcake with “The Works,” strawberry pies and desserts, Mike’s Barbecue, quality artisans, live music by The Bushmill Band and Folk Salad, and a performance by the So. MD Bootscooters at 1:30 pm. Proceeds support local charities in St. Mary’s County. Free admission.
College Sailing Nationals at St. Mary’s College of Maryland from May 20–23, located at The James P. Muldoon River Center and The Teddy Turner Waterfront, 47498 Trinity Church Rd, Lexington Park, MD – Watch as 36 college teams from across the country compete in the ICSA Women’s Fleet Race National Championships. Teams will race in semifinals to earn their spot in the finals and a shot at the national title. FREE for spectators.
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 16th
4:00pm – Copper Pennies – Lyon Family Farm – Mechanicsville MD
5:00pm – Dust on the Bottle – Running Hare Winery – Prince Frederick MD
5:00pm – Loose Change – Happy Harbor Restaurant – Deale MD
5:00pm – Brian Grumbine – Greene Turtle Sports Bar – La Plata MD
5:00pm – Jack Allen – The Slice House – Leonardtown MD
5:00pm – One Foot in the Groove – Mully’s Brewery – Prince Frederick MD
5:00pm – Greg Barrick & David Hamner – C & R Pub – Towson MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:30pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Doc Lohn – The Local – Hollywood MD
5:00pm – Ryan Forrester – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Hyland Brothers – Kellam’s Field – Chesapeake Beach MD
6:00pm – John Luskey – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Doc Marten & the Flannels – The TIKI Bar – Solomons MD
6:00pm – Joe Parsons – Southern Trail Distillery – Mechanicsville MD
6:00pm – Funkzilla – Wheel House Beer Garden – North Beach MD
6:30pm – Billy Breslin – Ruddy Duck Brewery & Grill – Solomons MD
6:30pm – Ben Connelly – Bugeye Grill – Solomons MD
7:00pm – Shane Graham – O’Gannigan’s Pub – Prince Frederick MD
7:00pm – Mike Mead Band – Seabreeze Tiki Bar – Mechanicsville MD
8:00pm – Hot Ice – Phil’s Place – Hughesville MD
8:00pm – Carpool (Cars tribute) – The Rex Theatre – Leonardtown MD
8:00pm – Tommy McGee Band – Toots Bar – Hollywood MD
8:30pm – Others May Fall – The Tavern – Saint Leonard MD
Saturday – May 17th
10:00am – Byron Ciotter – Bugeye Grill – Solomons MD
11:00am – David Norris – Historic Sotterley Plantation – Hollywood MD
11:30am – Joseph Norris – Historic Sotterley Plantation – Hollywood MD
12:00pm – Fran Scuderi – Running Hare Winery – Prince Frederick MD
12:30pm – Mark Tatum – Two Lions Vineyards – Upper Marlboro MD
1:00pm – All Funked Up – Historic Sotterley Plantation – Hollywood MD
1:00pm – Ryan Forrester – Happy Harbor Restaurant – Deale MD
2:00pm – The Lucky Few – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Reluctant Jazz Band – Corteau Vineyards – Mechanicsville MD
2:00pm – Shortcut Sunny – Robin Hill Farm & Vineyards – Brandywine MD
2:30pm – Copper Pennies – Historic Sotterley Plantation – Hollywood MD
3:00pm – The Websters – Wheel House Beer Garden – North Beach MD
3:00pm – Noel Duke & Friends – The Scuttlebutt – Cobb Island MD
3:00pm – BK Fest – Twisted Bar & Grill – Hollywood MD
————– SMIBS, Assembly 6, Stone Brew, Censored Image,
————— (Mystery Band),Vivid Vertigo, Red Skies Dawning & Slic –
4:00pm – Thunderball – Apehangers Bar & Grill – Bel Alton MD
5:00pm – Dust on the Bottle – Anthony’s Bar & Grill – Dunkirk MD
5:00pm – Josh Airhart – Running Hare Winery – Prince Frederick MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:30pm – Faith Noel – Blue Fish Pub – Solomons MD
6:00pm – Eli Young Band & Blanco Brown – Regency Stadium – Waldorf MD
6:00pm – Monkey Business – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Kavoossi – Wheel House Beer Garden – North Beach MD
6:00pm – Loose Change – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Be Kind Rewind – The TIKI Bar – Solomons MD
6:00pm – Nightcap – Southern Trail Distillery – Mechanicsville MD
6:30pm – John Luskey – Bugeye Grill – Solomons MD
7:00pm – Sean P – Pax River Ale House – Lexington Park MD
7:00pm – Billy Breslin – Neptune’s Seafood Pub – North Beach MD
7:00pm – Lunatic Fringe – Seabreeze Tiki Bar – Mechanicsville MD
8:00pm – EchoKarma – Buckets Bar & Grill – Lusby MD
8:00pm – Midnight Sunsets – Toots Bar – Hollywood MD
8:30pm – Comedy Night – The Taphouse 1637 – California MD
8:30pm – Jack Allen – The Sky Bar – Fredericksburg VA
9:30pm – Girl Crush – Apehangers Bar & Grill – Bel Alton MD
Sunday – May 18th
11:00am – Chaptico Songworks – Sotterley Plantation – Hollywood MD
11:30am – Joseph Norris – Historic Sotterley Plantation – Hollywood MD
12:00pm – Jack Allen – Miller Farm Strawberry Festival – Clinton MD
1:00pm – Hyland Brothers – Running Hare Winery – Prince Frederick MD
1:30pm – Wes Ryce – Historic Sotterley Plantation – Hollywood MD
2:00pm – Shortcut Sunny – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Pete Best – Wharf 38 – Deale MD
2:00pm – Nightcap – Port of Leonardtown Winery – Leonardtown MD
2:30pm – HydraFX – Historic Sotterley Plantation – Hollywood MD
3:00pm – Billy Breslin – Coast 2 Coast Seafood Bar – Solomons MD
3:00pm – 3 of a Kind – Wheel House Beer Garden – North Beach MD
3:00pm – Matt Guilherme – Toots Bar – Hollywood MD
3:00pm – John Luskey – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Vikki Roberts Band – Happy Harbor Restaurant – Deale MD
3:00pm – Joe Matthews Band – The Potomac Gardens – Coltons Point MD
3:00pm – Side Hustle – Seabreeze Tiki Bar – Mechanicsville MD
3:00pm – Social – The TIKI Bar – Solomons MD
3:00pm – Audra & Johnny – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Funkzilla Unplugged – The Pier – Solomons MD
5:00pm – Doc Lohn – Bugeye Grill – Solomons MD
Monday – May 19th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – May 20th
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – May 21st
5:00pm – John Luskey – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Chris Dean – The Pier – Solomons MD
6:00pm – Levi Stephens – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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