SOUTHERN MARYLAND — From outdoor festivals and farm celebrations to sunset concerts and pride kickoffs, Southern Maryland has a full slate of events this week for all ages and interests. Whether you’re picking berries, catching a world premiere concert, or hiking by moonlight, there’s no shortage of ways to connect with your community across Calvert, Charles, and St. Mary’s counties.
To have your upcoming event featured, please enter your event information on our Events Calendar.
CALVERT COUNTY
DJ J-Spin on May 30 (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 Hike on May 30 (8:30 to 9:30 p.m.), located at Wetlands Overlook Park, 4030 11th St, North Beach, MD 20714 – Explore nature after dark with a guided evening hike led by a naturalist. Open to all ages. Dress for the weather and bring water, bug spray, and a flashlight. Free admission. Registration may be required.
Spring Fling on the Farm on May 31 (10 a.m. to 3 p.m.), located at King Family Farm, 655 Ray Rd, Sunderland, MD 20689 – Enjoy a fun-filled day with local crafters, vendors, and food trucks at this free spring celebration on the farm. Free admission.
Bill Butler Live on May 31 (7 p.m.), located at Bay Wine and Spirits, 9100 Bay Ave #103, North Beach, MD 20678 – Enjoy an evening of live music as Bill Butler returns to perform in this intimate coastal venue. Free admission.
Neptune’s 40th Anniversary Celebration on May 31 (starting at 12 p.m.), located at Neptune’s Seafood Pub, 8800 Chesapeake Ave, North Beach, MD 20714 – Celebrate four decades of local flavor with live music, cornhole tournaments, kids’ activities, raffles, and great food and drinks. The first 40 attendees will receive a commemorative 40th anniversary shirt. Free admission.
DJ Kobe on May 31 (9 p.m. to close), located at Rod ‘N’ Reel Resort: Gaming Building, 4150 Mears Avenue, Chesapeake Beach, MD – Dance the night away with DJ Kobe spinning live on the first floor of the Gaming Building. Enjoy music, pull-tab machines, and drinks in a lively atmosphere. Free admission.
Children’s Day on the Farm on June 1 (11 a.m. to 4 p.m.), located at Jefferson Patterson Park & Museum, Jefferson Patterson Park Entra Rd, St. Leonard, MD 20685 – Celebrate the 38th annual Children’s Day with wagon rides, crafts, games, live performances, food vendors, and hands-on exhibits exploring rural life past and present. Free admission.
DMV Wine and Chill Meetup on June 1 (12 p.m. to late), located at Running Hare Vineyard, 150 Adelina Rd, Prince Frederick, MD 20678 – Join DMV Does for an afternoon of wine, live music, food trucks, games, and springtime vibes. Perfect for wine enthusiasts, foodies, and those looking to connect socially in a beautiful outdoor setting.Tickets required..
Prekindergarten & Kindergarten Round Up on June 3 (5:30 to 7:00 p.m.), located at Barstow Elementary School, 295 J W Williams Road, Prince Frederick, MD – This annual event welcomes Calvert County families with children eligible for Pre-K or Kindergarten in the 2025–2026 school year. Families can engage in learning games, meet local agencies, and enjoy a frozen treat. Enrollment assistance will be available. Free admission.
Sea Squirts: Seasonal / Summer-Time on June 5 (10:15 a.m. and 11:15 a.m. sessions), located at Calvert Marine Museum, 14200 Solomons Island Road S, Solomons, MD 20688 – Children ages 18 months to 3 years, accompanied by an adult, are invited to explore the museum through music, stories, and hands-on seasonal activities. Each session includes story time and a themed craft (available while supplies last). Held at the Corbin Nature Pavilion, weather permitting, or indoors in the Harms Gallery. Free with museum admission.
For more Calvert County events, visit the Calvert County Maryland website.
CHARLES COUNTY
Town of La Plata Summer Concert Series with Steve Potter Blues Band on May 30 (7 p.m.), located at La Plata Town Hall Lawn, 305 Queen Anne Street, La Plata, MD – Bring a blanket or lawn chair and enjoy live music under the stars as the town’s beloved Summer Concert Series returns! Concerts run every Friday through August 23 with a mix of country, jazz, oldies, military bands, and classic rock. Free admission.
NCAC’s 5th Annual NatureFest on May 31 (10 a.m. to 2 p.m.), located at College of Southern Maryland, 8730 Mitchell Road, La Plata, MD – Explore the wonders of nature through hands-on activities, educational exhibits, and outdoor fun at this free community event for all ages. Free admission.
Prep for Pride on May 31 (6 to 9 p.m), located at Center for Abused Persons, 2670 Crain Hwy, Waldorf, MD 20601 – Get ready to celebrate and connect at this community-focused kickoff to Pride Month. Hosted by FreeState Justice, this event features LGBTQ+ resources, refreshments, affirming spaces, music, and conversations centered around identity, support, and empowerment. Allies and advocates welcome. Free admission.
World Premier Concert on May 31 (5 to 6:00 p.m.), located at Christ Church, 112 Charles St, La Plata, MD – A special father-son concert featuring Dr. Osman Kivrak and Andrew Kivrak performing viola and organ works. Highlights include the world premiere of Oliver’s Journey for Viola and Organ by Rob Vuono, Jr., alongside pieces by Sowerby, Eccles, W.F. Bach, and Widor Free; donations accepted.
Mommy and Me Royal Tea Party on May 31 (11 a.m. to 4 p.m.), located at Classique Atelier, 4409B Southern Business Park Dr, White Plains, MD – Enjoy a magical afternoon of fancy dress-up, delicious treats, and tea-time fun for mothers and children alike. Tickets available on Eventbrite.
Beats, Rhymes, & Rhythms on May 31 (2 to 4 p.m.), located at College of Southern Maryland, 8730 Mitchell Rd, La Plata, MD – Explore the power of music through rhythm and lyricism in this creative and engaging performance experience. Free admission.
4 The Cool In You Wine and Music Festival on May 31 (12 to 9 p.m.), located at 8440 Fairground Rd, La Plata, MD 20646 – Enjoy an afternoon of wine tasting, live music, and vibrant entertainment at the 9th annual celebration hosted by Tricky Entertainment. Ticketed event.
Kids Night Out: Luau Adventure on May 31 (6 to 9:30 p.m.), located at My Gym Waldorf, 3303 Plaza Way, Waldorf, MD 20603 – Aloha, young adventurers! Join us for a fun-filled tropical journey through the gym with Hawaiian-themed crafts, a volcano experiment, island snacks, and a movie screening of Lilo & Stitch. Kids will make real flower lei necklaces, learn Hawaiian fun facts, and enjoy hands-on activities throughout the night. Don’t forget to wear your coolest Hawaiian shirt and bring your My Gym gripper socks and a water bottle! Ticketed event.
Golden Years at Graces on June 4 (12 to 3 p.m.), located at Graces Event Center, 4045 Renner Road, Waldorf, MD 20602 – A monthly celebration for the 50+ community featuring live entertainment and a lavish buffet, hosted by BRECORE Entertainment and Graces Event Center. A great time of music, food, and fellowship. $30 per person.
6th Annual Drive for Life Golf Tournament on June 5 (9 a.m.), located at Swan Point Yacht and Country Club, 11550 Swan Point Boulevard, Issue, MD – Support the Catherine Foundation at this charity golf tournament benefiting pregnant women and young families. In operation for over 40 years, the nonprofit provides free services and material assistance in Waldorf. Unique highlight: tee off with an AR-15 golf ball launcher on Hole 6 and send your shot soaring 300 yards. It’s literally a blast! Ticket Required.
For more Charles County events, visit the Charles County Maryland website.
ST. MARY’S COUNTY
Barre Class on May 30 (2 p.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Lane, Leonardtown, MD – This low-impact class from Zen Well Studio is designed for seniors to improve strength, flexibility, and balance through gentle, guided movements. $40. Advance registration required.
Spaghetti Dinner Dine-In or Carry-Out on May 31 (5 p.m.), located at 2nd District Social Hall, 45245 Drayden Rd., Valley Lee, MD – Enjoy a hearty dinner featuring spaghetti with meat or veggie sauce, green beans, garden salad, garlic bread, and dessert. Adults: $15; Children 6–12: $7; Kids 5 & under eat free.
For the Love of Our Animals on May 31 (11 a.m. to 2 p.m.), located at Summerseat Farm, 26655 Three Notch Rd, Mechanicsville, MD 20659 – Celebrate the animals of Summerseat Farm with family-friendly fun, including feeding stations, games, and a scavenger hunt. Meet sheep, goats, pigs, rabbits, donkeys, llamas, and more. Free event; donations appreciated.
Best of Both Berries on May 31 (All day, 7 hours), located at Lyon Family Farms, 39010 Lyon Ln, Mechanicsville, MD 20659 – Celebrate the sweetest time of the year with both strawberries and blueberries in season. Enjoy berry picking, a moon bounce, yard games, and treats from local food trucks, including OTP Wing Wagon, Sonny Boy Donuts, and Lucky Dog Snow Cones. Free admission.
Indoor Yard Sale on May 31 (7 a.m. to 1 p.m.), located at Mt. Zion United Methodist Church, 27108 Mt. Zion Church Road, Mechanicsville, MD – Free admission.
Women Veterans Paddle on May 31 (9 a.m. to 12 p.m.), located at St. Mary’s River Watershed Park, 21250 Camp Cosoma Road, Leonardtown, MD – Join a guided group paddle for women veterans and active duty service members. Beginners and wounded warriors welcome. Kayaks provided or bring your own. Lunch provided by Operation Second Chance. Free for eligible participants. Registration required.
Afroman Concert on June 1 (5 to 7 p.m.), located at The Rex Theatre, 22695 Washington St, Leonardtown, MD 20650 – Catch the legendary Afroman live with special guests The Copper Pennies Band in an unforgettable night of music, comedy, and storytelling. Doors open at 4:00 p.m. Tickets start at $42.
Magazine Flower-Making Class on June 4 (2:30 p.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Ln, Leonardtown, MD – Turn magazines into decorative flowers. All supplies and glass vases provided. Advance registration required. Tickets $5.
Morning Pickleball 101: Just Dink It on June 4 (9 to 11 a.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Ln, Leonardtown, MD – Learn pickleball fundamentals, including shot techniques, scoring, rules, and court strategy. Loaner paddles provided. Advance registration required. Free admission.
Digital Photography for Beginners: Presentation & Workshop on June 5 (1 to 4 p.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Learn photography fundamentals with expert Orlando Thompson during this free educational session and hands-on workshop. Topics include lighting, composition, and storytelling through images. Bring your own camera. 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 30th
5:00pm – Chris Dean – Greene Turtle Sports Bar – California MD
5:00pm – Doc Lohn – Greene Turtle Sports Bar – La Plata MD
5:00pm – Levi Stephens – Happy Harbor Restaurant – Deale MD
5:00pm – Dust on the Bottle – Corteau Vinyards – Mechanicsville MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
6:00pm – GypsySol – Blue Fish Pub – Solomons MD
6:00pm – Good Talk Russ – Wheel House Beer Garden – North Beach MD
6:00pm – Bicycle Day – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Richard Wagner & Rosemarie Stanek – Ruddy Duck – Solomons MD
6:00pm – Mike Mead – The Local – Hollywood MD
6:00pm – HydraFX – The TIKI Bar – Solomons MD
6:30pm – Audra Keeler & Johnny Brown – American Legion 274 – Lusby MD
6:30pm – Billy Breslin – Bugeye Grill – Solomons MD
6:30pm – John Luskey – Fitzie’s Bar & Marina – Leonardtown MD
7:00pm – Steve Potter Band – Town Hall Concert Series – La Plata MD
8:00pm – Latrice Carr – Coast 2 Coast – Solomons MD
8:00pm – Framing The Tinman – Toots Bar – Hollywood MD
9:00pm – Justin Taylor Band – Twisted Bar & Grill – Hollywood MD
Saturday – May 31st
10:00am – Byron Ciotter – Bugeye Grill – Solomons MD
12:00pm – John Singleton – Running Hare Winery – Prince Frederick MD
12:00pm – The Blakbyrds – Neptunes Seafood Pub – North Beach MD
12:30pm – Vince Borelli – Two Lions Vineyards – Upper Marlboro MD
2:00pm – Chris Dean – Bayard House – Chesapeake City MD
2:00pm – Nightcap – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Justin Moyar – Port of Leonardtown Winery – Leonardtown MD
3:00pm – Morgan Tripp Band – Neptunes Seafood Pub – North Beach MD
4:00pm – Richard Hayward – Happy Harbor Restaurant – Deale MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Monkey Business – Running Hare Winery – Prince Frederick MD
5:00pm – Audra Keeler & Johnny Brown – Bugeye Grill – Solomons MD
5:30pm – The Rise Band & Show – Blue Fish Pub – Solomons MD
5:30pm – Sister Midnight – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Troll Tribe – Wheel House Beer Garden – North Beach MD
6:00pm – Copper Pennies – Southern Trail Distillery – Mechanicsville MD
6:00pm – New Normal – The TIKI Bar – Solomons MD
6:00pm – Midnight Sunsets – Seabreeze Tiki Bar – Mechanicsville MD
7:00pm – The Neverland Band – Brüdergarten @ SOF – Leonardtown MD
7:00pm – Chandler Finch – Pax River Ale House – Lexington Park MD
7:00pm – Joey Tippett – The Brass Tap – California MD
7:00pm – Radio Redline – The Scuttlebutt – Cobb Island MD
7:00pm – Moose Jaw Bluegrass – Neptunes Seafood Pub – North Beach MD
7:00pm – Women In Country – Dodge Perf. Arts Center – St. Mary’s City MD
8:00pm – Sam L Smith – The Potomac Gardens – Coltons Point MD
8:00pm – Twist of Fate – Toots Bar – Hollywood MD
8:00pm – Hot Ice – Martini’s Lounge – White Plains MD
8:00pm – Hit or Miss – The Rex Theatre – Leonardtown MD
8:30pm – Blazin’ Keys Dueling Pianos – The Taphouse 1637 – California MD
8:30pm – Jack Allen – The Sky Bar – Fredericksburg VA
8:30pm – Greg & Friends- Ollie’s Bar & Grill – La Plata MD
———- Greg Barrick, John Luskey, Mike Trujillo & Justin Myles –
9:00pm – Dying Breed – Apehangers Bar & Grill – Bel Alton MD
Sunday – June 1st
1:00pm – Levi Stephens – Running Hare Winery – Prince Frederick MD
2:00pm – Peter James – Robin Hill Farm & Vineyards – Brandywine MD
2:00pm – Sister Midnight – Rod & Reel Resort – Chesapeake Beach MD
2:00pm – Audra & Johnny – Wilderness Run Vineyard – Spotsylvania VA
2:00pm – Justin Myles – Wharf 38 – Deale MD
2:30pm – Brian Grumbine – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – Hyland Brothers – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Kevin Lee – Wheel House Beer Garden – North Beach MD
3:00pm – Boys of Summer – The TIKI Bar – Solomons MD
3:00pm – Andy, Shawn & Todd – The Pier – Solomons MD
3:00pm – Emegran – Coast 2 Coast Seafood Bar – Solomons MD
3:00pm – Viands & Co. – Traders Seafood & Ale – Chesapeake Beach MD
3:00pm – St. Maries Choral Arts – Dodge Arts Center – St. Mary’s City MD
3:00pm – Nightcap – Seabreeze Tiki Bar – Mechanicsville MD
3:00pm – Greg Barrick – Toots Bar – Hollywood MD
4:00pm – Ryan Forrester – Happy Harbor Restaurant – Deale MD
5:00pm – Afroman / Copper Pennies – The Rex Theatre – Leonardtown MD
5:00pm – Doc Lohn – Bugeye Grill – Solomons MD
Monday – June 2nd
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – June 3rd
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – June 4th
6:00pm – Nightcap – The Pier – Solomons MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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