SOUTHERN MARYLAND — Southern Maryland is packed with events this week as the region heads into peak springtime fun. From live music and community expos to Mother’s Day brunches and kids’ craft fairs, this week’s lineup includes dozens of opportunities to connect, create, and celebrate. Highlights include the Solomons Maritime Festival, food truck nights, hiring events, car shows, and outdoor movie screenings. Whether you’re planning a family outing or looking for something new in your neighborhood, there’s plenty happening across Calvert, Charles, and St. Mary’s counties.
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CALVERT COUNTY
Annmarie After Hours Presents: “Imaginary Worlds” on May 9 (5 p.m.), located at Annmarie Sculpture Garden & Art Center, 13470 Dowell Road, Solomons, MD – Enjoy an adults-only evening with extended gallery hours, live music by Aldous & Emma, and a cash bar featuring wine, local beer, and food from Bowl 29. $5 (AMG Members Free).
Food Truck Fridays at Annmarie on May 9 (5 to 7 p.m.), located at Annmarie Sculpture Garden and Arts Center, 13470 Dowell Road, Solomons, MD – Join us at Annmarie Sculpture Garden & Arts Center for extended hours! A food truck will be on site to serve you, as you wander our beautiful gardens and marvel at awe-inspiring sculptures and works of art.
DJ Big Tony on May 9 (9 p.m. to close), located at Rod ‘N’ Reel Resort: Gaming Building, 4150 Mears Avenue, Chesapeake Beach, MD – Join DJ Big Tony for a high-energy night of music and dancing on the first floor of the Gaming Building. Enjoy drinks, pull-tab games, and a lively atmosphere. Free admission.
11th Annual Calvert Arts Festival on May 10 (10 a.m. to 5 p.m.), located at All Saints’ Episcopal Church, 100 Lower Marlboro Road, Sunderland, MD – Sample flavorful wines and craft beers from Maryland makers for a $20 fee with your souvenir tasting glass and wristband. No fee to shop from outstanding local juried artisans. Enjoy delicious food and beverages, live entertainment, children’s crafts, raffles, bid on unique silent auction items & more. Tour our 1692 church & labyrinth. Event is rain or shine. Free admission and parking. Fee ($20) for wrist band and tasting glass for alcoholic beverages. Proceeds benefit community charities. To date, we have raised nearly $78,000.
Mother’s Day Maker’s Market at Annmarie on May 10 (9 a.m. to 12 p.m.), located at Annmarie Sculpture Garden & Art Center, 13470 Dowell Road, Solomons, MD – Shop a curated selection of handmade goods including jewelry, art, home décor, and small-batch foods—perfect for Mother’s Day gifting. FREE.
Mother’s Day Dinner Buffet on May 11 (3:30 to 7 p.m.), located at Rod ‘N’ Reel Resort, 4160 Mears Ave, Chesapeake Beach, MD – Treat mom to a waterfront buffet featuring prime rib, southern ham, flavorful sides, and decadent desserts. Includes coffee, tea, and lemonade; cash bar available. Celebrate with family in a relaxing, scenic setting. Tickets required.
Chesapeake Grille and Deli Fundraiser on May 13 (11 a.m. to 9 p.m.), located at Chesapeake Grille and Deli, 10092 Southern Maryland Boulevard, Dunkirk, MD – No cook Tuesday, come in or order out, proceeds will benefit the Humane Society of Calvert County.
Little Minnows: Hungry Caterpillar/Butterfly on May 15 (sessions at 10:15 a.m. and 11:15 a.m.), located at Calvert Marine Museum, Harms Gallery, 14200 Solomons Island Road South, Solomons, MD – Preschoolers (ages 3–5) and their caregivers are invited for themed story time and a craft, while supplies last. Sessions run 25–40 minutes. FREE with museum admission.
For more Calvert County events, visit the Calvert County Maryland website.
CHARLES COUNTY
Library Crate for Teens on May 9 (All Day), located at P.D. Brown Memorial Branch, 50 Village Street, Waldorf, MD – Teens ages 12–18 can register for a free personalized book box, which includes a library book to borrow and mystery goodies to keep. Registration is required and open while supplies last. FREE.
Reading Program and Animal Lovers Night on May 9 (6:35 p.m.), located at Southern Maryland Blue Crabs Stadium, 11765 Saint Linus Dr, Waldorf, MD – Students who complete the Pinch Onto Books reading program receive a free ticket and can participate in a pregame parade. The event also features a petting zoo and the Mutts Gone Nuts performance. Gates open at 5:30 p.m. Tickets Required.
JCPenney Kid Zone Craft Event on Saturday, May 10 (11 a.m. to 12 p.m.), located at JCPenney, 11130 Mall Circle, Waldorf, MD – Kids can enjoy a free craft activity, receive an ID badge, lanyard, and collector’s pin. Held on the second Saturday of every month. FREE.
Moonlight Movie Nights on May 10 (at dusk), located at The Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – Bring the whole family out for an evening under the stars with a free outdoor movie screening. Held the second Saturday of each month, May through September. Free admission. Rain date: May 17.
Mother’s Day Karaoke Brunch on May 11 (3 to 6 p.m.), located at Grace’s Event Center, 4045 Renner Road, Waldorf, MD – Celebrate Mother’s Day with brunch, a complimentary mimosa, and a fun-filled karaoke session.Tickets Required
World No Tobacco Day 2025 Art and Poetry Showcase on May 13 (6 p.m.), located at Westlake High School, 3300 Middletown Rd, Waldorf, MD – A creative evening highlighting youth voices through art and poetry, raising awareness about the dangers of tobacco and nicotine use among young people. Open to students in grades 6–12. Free admission; submissions accepted on-site.
14th Annual Southern Maryland Hiring Event on May 14 (10 a.m. to 4 p.m.), located at the College of Southern Maryland, La Plata Campus (N Campus Dr, BI Building), La Plata, MD – The region’s largest job fair returns to connect jobseekers with over 65 employers and 20 resource partners. This year’s event is especially important amid ongoing federal layoffs. Attendees can access a mobile app for resume sharing and job search tips, receive a free professional headshot, and explore career support services. Hosted by the Tri-County Council for Southern Maryland in partnership with the College of Southern Maryland and the Rural Maryland Council. Free admission. Full details at www.tccsmdg
Bike to Work Day 2025 on May 15 (6:30 to 9 a.m.), with over 100 pit stops across the DC Metro Region including DC, Suburban Maryland, and Northern Virginia – Join thousands of commuters for the 24th annual celebration of biking as a healthy, eco-friendly, and cost-effective way to travel. Enjoy giveaways, food, beverages, and a chance to win prizes. The first 18,000 registrants who attend a pit stop will receive a free Bike to Work Day T-shirt. Free with registration.
For more Charles County events, visit the Charles County Maryland website.
ST. MARY’S COUNTY
Spring Craft & Vendor Show – OPEN TO THE PUBLIC on May 9 (10 a.m. to 3 p.m.), located at Loffler Senior Activity Center, 21905 Chancellors Run Road, Great Mills, MD – Find unique Mother’s Day gifts, home décor, and crafts while supporting local crafters and seniors. Food trucks will be onsite. Free
Plant Sale at Summerseat Farm on May 10 (8 a.m. to 2 p.m.), located at Summerseat Farm, 26655 Three Notch Rd, Mechanicsville, MD – Browse a vibrant selection of perennials, annuals, native plants, vegetables, herbs, ornamental grasses, trees, and tropicals. Breakfast and lunch available on-site, plus “Llama Beans” organic fertilizer for sale. Free admission. Rain or shine.
Touch a Truck & Car Show on May 10 (10 a.m.), located at Father Andrew White School, 22850 Washington Avenue, Leonardtown, MD – Explore service vehicles, classic cars, and more at this family-friendly fundraiser for the FAW DI teams heading to the Global Finals Tournament. Enjoy raffles, door prizes, a State Trooper helicopter landing, and vote for your favorite car. Free admission; raffle tickets available on-site.
JCPenney’s Kid Zone on Saturday, May 10 (11 a.m. to 12 p.m.), located at JCPenney, 23415 Three Notch Rd, Ste 2016, California, MD – Kids can enjoy a free craft activity, receive an ID badge, lanyard, and collector’s pin. Held on the second Saturday of every month. FREE.
Reggie Rice – Fool of Illusions Show on May 10 (6:30 p.m.), located at The King’s Christian Academy, 20738 Point Lookout Road, Callaway, MD – Enjoy a night of laughs and magic with 3x DC Comedy Magician of the Year Reggie Rice, as he brings his high-energy, family-friendly illusion show to Southern Maryland.Tickets required at www.foolofillusions.com or www.kcaeagles.org.
SMTMD Contra Dance on May 10 (7 to 9:30 p.m.), located at Christ Episcopal Church Parish Hall, 37497 Zach Fowler Road, Chaptico, MD – The evening starts at 7 pm with a half hour beginner’s dance workshop followed by live music performed by the SOMD Open Band and dancing from 7:30 to 9:30 pm. Check the website calendar for the lineup of dances and callers. Admission: $8 for members; $12 for non‐SMTMD members; children 17 and under (when accompanied by a paying adult) and band members are free.
Mother’s Day Weekend – Mom’s Tours Are Free on May 10–11, located at Historic Sotterley, 44300 Sotterley Lane, Hollywood, MD – Celebrate Mother’s Day with a visit to Historic Sotterley, where moms receive free admission to guided Manor House tours. Tours will focus on the women who shaped Sotterley’s history and take place Saturday at 10:30 a.m., 12:30 p.m., and 2:00 p.m., and Sunday at 12:30 p.m. and 2:00 p.m. Other guests must purchase tickets at the Visitor Center. Grounds are open for picnics, trail walks, and more. Regular admission prices apply for non-mothers.
Pax River Quilters Guild Meeting on May 12 (6:30 p.m.), located at Hollywood United Methodist Church, Marvel Dean Road, Hollywood, MD – Join fellow quilting enthusiasts for the guild’s monthly meeting featuring guest speakers, show and tell, and community service projects. Open to quilters of all skill levels. Free to attend.
Chess Club at Swords and Spoons on May 13 (6 to 8 pm), located at Swords and Spoons, 22599 MacArthur Boulevard, Suite 126, California, MD – Join the Pax Strategy Club at Swords and Spoons for a night of chess. Free entry.
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 9th
5:00pm – Greg Barrick – Mully’s Brewery – Prince Frederick MD
5:00pm – Swamp Weasels – Running Hare Winery – Prince Frederick MD
5:00pm – Jason Bishop – Happy Harbor Restaurant – Deale MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:30pm – David Norris – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Jayce Paris – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – John Luskey Duo – Dockside Tiki Bar – Colonial Beach VA
6:00pm – Mike Ferro – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Turning The Tide – The TIKI Bar – Solomons MD
6:00pm – Mallow Hill – Wheel House Beer Garden – North Beach MD
6:00pm – Byron Ciotter – Bugeye Grill – Solomons MD
6:00pm – Smoke Signals – Swan Point Country Club – Swan Point MD
7:00pm – 4th Wall Break – Seabreeze Tiki Bar – Mechanicsville MD
7:00pm – Cheers To Comedy – Running Hare Winery – Prince Frederick MD
7:00pm – Jack Allen – O’Gannigan’s Irish Pub – Prince Frederick MD
8:00pm – In Too Deep – Toots Bar – Hollywood MD
8:30pm – Flying Ivories Dueling Pianos – The Tavern – Saint Leonard MD
Saturday – May 10th
11:00am – Audra & Johnny – Dockside Tiki Bar – Colonial Beach VA
11:00am – Joseph Norris – Summerseat Farm – Mechanicsville MD
11:00am – Food Truck Fest – Calvert Co Fairgrounds – Prince Frederick MD
————– 12:45 – Cosmic Symphony, 2 – Hyland Brothers, 3:15 – Blakbyrds –
12:00pm – Pork Donut – Southern Trail Distillery – Mechanicsville MD
12:00pm – Ryan Webster – Running Hare Winery – Prince Frederick MD
12:30pm – Michael Kelly – Two Lions Vineyards – Upper Marlboro MD
1:00pm – Richard Hayward – Neptunes Seafood Pub – North Beach MD
2:00pm – Levi Stephens – JaneMark Winery – Brandywine MD
2:00pm – Logan Kraft Band – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Mike Mead – Robin Hill Farm & Vineyards – Brandywine MD
3:00pm – Arkansas Williams – Happy Harbor Restaurant – Deale MD
3:00pm – Girl Crush – The Boathouse @ Anchored Inn – Deale MD
4:00pm – HydraFX – The Taphouse 1637 – California MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Bandwidth No Name – Running Hare Winery – Prince Frederick MD
5:00pm – Squid Inc – Billiken’s Smokehouse – Fredericksburg VA
6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Hyland Brothers – Skippers Pier – Deale MD
6:00pm – Stacy Brooks – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Weird Science – The TIKI Bar – Solomons MD
6:00pm – Shane Graham – The Local – Hollywood MD
6:00pm – Loose Change – Wheel House Beer Garden – North Beach MD
6:30pm – 15 Strings – Blue Fish Pub – Solomons MD
7:00pm – Basement Snakes – O’Gannigan’s Irish Pub – Prince Frederick MD
7:00pm – Bangerz Only – Seabreeze Tiki Bar – Mechanicsville MD
7:30pm – Levi Stephens – Pax River Ale House – Lexington Park MD
8:00pm – Linwood Taylor & Still Standing – Buckets Bar & Grill – Lusby MD
8:00pm – Drivetrain – The Tavern – Saint Leonard MD
8:00pm – Ally Venable Band / Byron Ciotter – Rex Theatre – Leonardtown MD
9:00pm – Sister Midnight – Twisted Bar & Grill – Hollywood MD
Sunday – May 11th – Mothers Day
10:00pm – T&T Steel Drum Band – Apehangers Bar & Grill – Bel Alton MD
12:00pm – Jack Allen – Miller Farm Strawberry Festival – Clinton MD
1:00pm – Out of Order – Running Hare Winery – Prince Frederick MD
2:00pm – Waters Edge Band – Apehangers Bar & Grill – Bel Alton MD
2:00pm – Justin Allen – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Coastal Jazz – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Just Us – Wharf 38 – Deale MD
3:00pm – Charles Co. Youth Orch. – Thomas Stone High – Waldorf MD
3:00pm – Richard Wayward – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Jason Bishop – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Andy Kuhn & Shawn – The Pier – Solomons MD
3:00pm – The Betas – Wheel House Beer Garden – North Beach MD
3:00pm – Hyland Brothers – Happy Harbor Restaurant – Deale MD
3:00pm – Wes Spangler – Seabreeze Tiki Bar – Mechanicsville MD
3:00pm – Rob Blake & David Hamner – Dockside Sports Bar – Deale MD
Monday – May 12th
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – May 13th
6:00pm – Hyland Brothers – Ketch 22 Restaurant – Deale Md
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – May 14th
5:00pm – Pete Best – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Greg Barrick – The Pier – Solomons MD
6:00pm – Hyland Brothers – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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