SOUTHERN MARYLAND — Labor Day weekend brings plenty of ways to celebrate across Southern Maryland, from jousting tournaments and sunflower festivals to vineyard movies. You can paddle out in Solomons, laugh along at Mully’s “track and field” games, or gather your crew for some paintball battles. Take the opportunity to explore every corner of the region this long weekend with our full list of events.
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THINGS TO DO IN CALVERT COUNTY
Live Music at The Dock: Hyland Brothers on Aug. 29 (7 p.m.), located at The Dock at Rod ‘N’ Reel Resort, 4160 Mears Avenue, Chesapeake Beach, MD – Enjoy live waterfront entertainment with the Hyland Brothers, paired with great food, refreshing drinks, and scenic Chesapeake Bay views. Free admission.
158th Annual Calvert County Jousting Tournament on Aug. 30 (10 a.m. to 6 p.m.), located at Christ Church, 3100 Broomes Island Road, Port Republic, MD – Enjoy a church bazaar, children’s activities, and organ recitals before the noon jousting tournament, followed by a traditional church supper with homemade fare. Free admission.
Saturday Social Paddle on Aug. 30 (8 to 10 a.m.), located at Patuxent Adventure Center, 155 Holiday Drive, Solomons, MD – Join a group paddle on the water to meet old friends and new. Rentals available through Patuxent Adventure Center. Rental fees apply.
ACLT Guided Canoe Trip on Aug. 30 (7 to 10 a.m.), launching from Parkers Creek Preserve, Chesapeake Bay, MD – Paddle up the scenic Parkers Creek with expert guides from the American Chestnut Land Trust. Explore over 3,200 acres of preserved wildlands and forests while learning about the area’s natural history. Canoes are available to borrow or participants may bring their own. Trips are physically demanding and not recommended for very young children or pets. $15 per person, registration required.
Campfire & Hayride on Aug. 30 (8 to 10 p.m.), located at Navy Recreation Center Solomons, 13855 Solomons Island Road, Solomons, MD – Gather around the campfire pit for s’mores (first 75 guests receive kits), wagon hayrides, music, and the chance to meet new friends. Free admission, open to all with base access.
Mully’s Track & Field Day on Aug. 30 (4:30 to 7:30 p.m.), located at Mully’s Taproom, 141 Schooner Lane, Prince Frederick, MD – Cheer on teams as they take on a hilarious lineup of beer-themed challenges including pint-carrying relays, beer can tosses, sack races, keg tosses, and sprints with a pint in hand. The competition is full, but spectators are welcome to come watch the fun. Free admission.
Jimmy Buffett Day Cruise on Aug. 30 (1 p.m., 3:45 p.m., and 6:30 p.m.), located at Solomons Island, 14443 Solomons Island Road, Solomons, MD – Set sail on the Chesapeake for a tropical-themed cruise celebrating the music and vibe of Jimmy Buffett. Tickets required.
Films in the Vines: The Sandlot on Aug. 30 (6 to 10 p.m.), located at Running Hare Vineyard, 150 Adelina Road, Prince Frederick, MD – Watch the classic film under the stars with vineyard views, food, and local craft beer and wine for purchase. $10 ticket.
Labor Day Bingo on Aug. 31 (11 a.m.), located at Rod ‘N’ Reel Resort – The Overlook, 4150 Mears Avenue, Chesapeake Beach, MD – Enjoy a holiday bingo game with cash prizes, advance ticket perks, and limited seating of 100 players. $40 tickets; advance sales include $10 in Free Play.
Sea Squirts: Terrific Turtles on Sept. 4 (10:15 and 11:15 a.m.), located at Calvert Marine Museum, 14200 Solomons Island Road South, Solomons, MD – Designed for children ages 18 months to 3 years with an adult, this interactive program features music, stories, and a craft focused on turtles. Included with museum admission; no registration required.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
Community Yoga at The Wills Group Fountain on Aug. 30 (9 to 10 a.m.), located at The Wills Group Fountain, 102 Centennial Street, La Plata, MD – Join Zentral Station instructors for a free outdoor community yoga session designed to start your weekend with balance and connection. Free admission.
Cars & Coffee Saturday Morning on Aug. 30 (8 a.m. to 1 p.m.), located at Apehangers Bar & Grill, 9100 Crain Hwy, Bel Alton, MD – Bring out your hot rods, trucks, and bikes for a community meetup over coffee and cars. Free admission.
Bowling + Brotherhood: Dad’s Event on Aug. 30 (1 p.m.), located at AMF Waldorf Lanes, 11920 Acton Lane, Waldorf, MD – An afternoon of strikes, laughs, and connection for dads, granddads, uncles, and male caregivers. Hosted by the Charles County Autism & Developmental Disabilities Parent Support Group with Together We Thrive. Military discounts available; pay alley directly.
Rhythm & Soul Brunch on Aug. 30 (10 a.m. to 1 p.m.), located at The Space by LBI, 2901 Festival Way, Waldorf, MD – Enjoy live music from The Artist Yu’Niq and Saxy Entertainment with Antonio, plus great food and cocktails. $40 early bird; group/table reservations available.
Southern Maryland Sunflower Festival 2025 on Aug. 30–31 (10 a.m. to 4 p.m.), located at Serenity Farm, 6932 Serenity Farm Rd, Benedict, MD – Celebrate the season with hayrides, face painting, petting pen, local art, photo ops, and more. Food vendors and market goods available; leashed dogs welcome. $12 advance / $15 at the gate; children 7 & under free.
Summer Soul Music Festival: Rare Essence on Aug. 31 (12 p.m.), located at Charles County Fairgrounds, 8440 Fairground Rd., La Plata, MD – Rare Essence headlines a Labor Day Weekend celebration featuring Junkyard, DC Vybe, Black Alley, and Major League Band, with music by DJ Frisco and DJ Rico. Tickets required.
Labor Day Play Day at Southern Maryland Paintball on Sept. 1 (10 a.m. to 4 p.m.), located at Southern Maryland Paintball, 11272 Edge Hill Rd., Newburg, MD – Spend your day off dodging paintballs instead of chores. Enjoy free admission, free rental gun, and free rental mask; just buy one bag of 400 paintballs for $29.95. Advance registration recommended.
Wild Raft Craft: Will it Sink or Float? on Sept. 2 (5:30 to 6:30 p.m.), located at P.D. Brown Memorial Branch, 50 Village St., Waldorf, MD – Kids ages 5–9 can build mini rafts with natural materials and test if they sink or float in this fun STEM-based activity. Registration required. Free admission.
Golden Life Thursday Fish Fry starting Sept. 4 (12 to 3 p.m.), located at Graces Event Center, 4045 Renner Road, Waldorf, MD – Enjoy a monthly afternoon of food, music, and fellowship featuring a classic fish fry. Held the first Thursday of each month. $25 admission.
Cute and Courteous Canines on Sept. 4 (10:45 to 11:45 a.m.), located at Charles County Public Library – La Plata Branch, 2 Garrett Avenue, La Plata, MD – Meet and interact with certified therapy dogs courtesy of Southern Maryland Pets on Wheels. Free admission.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
Yard Sale Extravaganza on Aug. 29–30 (7 a.m. start), located at Mt. Zion United Methodist Church, 27108 Mt. Zion Church Rd., Mechanicsville, MD – Shoppers can browse collectibles, books, dishware, furniture, clothes (new and used), toys, and more at this two-day sale. Donations will be accepted Sunday, Aug. 24 (12 to 4 p.m.) and Monday–Thursday, Aug. 25–28 (9 a.m. to 3 p.m.). Contact Brenda at 301-643-0668 with questions. Free admission.
SMTMD Old Time (Slow) Jam on Aug. 29 (4 p.m.), located at Summerseat Farm, 26655 Three Notch Rd., Mechanicsville, MD – Bring your instrument, chair, and beverage, or simply come to listen and enjoy traditional tunes from the Bushwood Mill Jam tune list. Beginners and all ages are welcome at this free community gathering hosted by the Southern Maryland Traditional Music and Dance (SMTMD), a nonprofit dedicated to preserving folk culture in the region. Free admission.
U-Pick Chardonel Grapes at Dixon Family Farm on Aug. 29 (5 to 8 p.m.), located at Dixon Family Farm, 27075 S. Sandgates Rd., Mechanicsville, MD – Bring your own bins and hand-pick Chardonel grapes, a premium white wine variety prized for its crisp flavor and balance. These award-winning grapes were used in the 2023 Maryland Governor’s Cup First Place Sparkling White Wine. Limited quantities available at $0.50 per pound.
End of Summer Bash on Aug. 30 (5 p.m. to dark), located at Leonardtown Wharf, Leonardtown, MD – Celebrate summer’s close with live music by Midnight Sunsets and Hydrafx, food, drinks, games, a trolley, and fireworks over the water. Family-friendly. Free admission.
Wine & Whiff on Aug. 30 (5:30 p.m.), located at Breton Bay Golf & Country Club, 21935 Society Hill Rd, Leonardtown, MD – Couples are invited for a fun nine-hole golf outing paired with drinks from The Ironwood Grill. Enjoy an evening of relaxed competition, good conversation, and great refreshments. Free for members / $30 per non-member player.
Patina Party 2025: Car Show, Swap Meet & Drag Race on Aug. 31 (10 a.m. to 4 p.m.), located at Maryland International Raceway, 27861 Budds Creek Road, Mechanicsville, MD – A full day of hot rods, rat rods, patina cars and trucks, vendors, food, drag racing, and family fun. Track entry $20, Car Show entry $5, Swap Meet entry $5 (one vehicle).
Sweet Summer Nights at Sotterley on Aug. 31 (7:30 to 9:30 p.m.), located at Historic Sotterley, 44300 Sotterley Lane, Hollywood, MD – Explore nature after dark with a guided night hike through fields and forests, calling owls, spotting foxfire, and identifying frog calls. Best for children ages 8+. Bring a flashlight—participants will receive an adapter to use at home. $5 non-members / free for members.
Afternoon Pickleball 101: Double Your Fun on Sept. 2 (2 p.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Lane, Leonardtown, MD – A three-week beginner-friendly class with twice-weekly sessions teaching the fundamentals and strategies of pickleball. Participants should bring water, non-marking shoes, and a paddle if they have one. Ticket required.
Beginner Beekeeping in Southern Maryland on Sept. 3 (4 p.m.), located at Garvey Senior Activity Center, 23630 Hayden Farm Lane, Leonardtown, MD – Learn the fundamentals of local beekeeping with Dee Wellons, President of the Association of Southern Maryland Beekeepers, including livestock comparisons and training opportunities, with an observation hive available weather permitting. Ticket required.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – August 29th
5:00pm – Chris Dean – Greene Turtle Sports Bar – California MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Brian Grumbine – Greene Turtle Sports Bar – La Plata MD
5:00pm – Stripped – Mully’s Brewery – Prince Frederick MD
5:00pm – Kevin Lee – Happy Harbor Restaurant – Deale MD
5:00pm – One Foot in the Groove – Corteau Vineyard – Mechanicsville MD
5:30pm – Sister Midnight – Running Hare Winery – Prince Frederick MD
5:30pm – Eddie Anderson – Robin Hill Vineyards – Brandywine MD
6:00pm – John Luskey – Stoney’s Clarkes Landing – Hollywood MD
6:00pm – Billy Breslin – The Local – Hollywood MD
6:00pm – Jason Bishop – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Ryan Forrester – Wheel House Beer Garden – North Beach MD
6:00pm – Midnight Sunsets – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – David Norris & Stu – Coast 2 Coast Seafood Bar – Solomons MD
6:00pm – Dixon Hall – Blue Fish Pub – Solomons MD
6:00pm – Thunderball – The TIKI Bar – Solomons MD
6:30pm – Ben Connelly – Bugeye Grill – Solomons MD
7:00pm – One Trick Pony – Fitzies Marina & Pub – Leonardtown MD
7:00pm – Russell Strange – The Taphouse 1637 – California MD
8:00pm – GrooveSpot Band & Show – Toots Bar – Hollywood MD
8:00pm – HydraFX – The Scuttlebutt – Cobb Island MD
8:30pm – Mariah Jean – Action Lounge & Billiards – Leonardtown MD
8:30pm – Taboo – Ollie’s Bar & Grill – La Plata MD
Saturday – August 30th
12:30pm – Nightcap – Serenity Farm Sunflower Fest – Benedict MD
12:00pm – Doc Lohn – Two Lions Vineyards – Upper Marlboro MD
1:00pm – Justin Trawick – Running Hare Winery – Prince Frederick MD
2:00pm – Eddie Pasa – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Folk Salad – Perigeaux Winery – Saint Leonard MD
2:00pm – Lawrence & Miner – Courteau Vineyards – Mechanicsville MD
2:00pm – Logan Kraft Band – POL Winery – Leonardtown MD
3:00pm – John Luskey – The Boathouse @ Anchored Inn – Deale MD
5:00pm – HydraFX / Midnight Sunsets – The Wharf – Leonardtown MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Justin Crenshaw – PTR Waterfront – Port Tobacco MD
5:00pm – Byron Ciotter – Port Oysteria & Brewery – Fredericksburg VA
5:30pm – Josh Airhart – Running Hare Winery – Prince Frederick MD
6:00pm – Karlee Ryce – The Local – Hollywood MD
6:00pm – Troll Tribe – Wheel House Beer Garden – North Beach MD
6:00pm – Red Jam – Traders Seafood Pub – Chesapeake Beach MD
6:00pm – Arkansas Williams – Happy Harbor Restaurant – Deale MD
6:00pm – Vicki Roberts Band – Dockside Restaurant & Bar – Deale MD
6:00pm – SouthBound 4 – Southern Trail Distillery – Mechanicsville MD
6:00pm – Doc Marten & The Flannels – The TIKI Bar – Solomons MD
7:00pm – Marianne Styles – The Brass Tap – California MD
7:00pm – Tornado Rose – Pax River Ale House – Lexington Park MD
7:00pm – One Trick Pony – Blue Fish Pub – Solomons MD
7:00pm – Funkzilla – Goose Bay Campground – Welcome Acres MD
8:00pm – Rattlesnake Pete – Buckets Bar & Grill – Lusby MD
8:00pm – Latrice Carr – Coast 2 Coast Seafood Bar – Solomons MD
8:00pm – 4th Wall Break – Wild Bill’s – Ocean City MD
8:00pm – Hate The Toy – Seabreeze Tiki Bar – Mechainicsville MD
8:00pm – Copper Pennies – Toots Bar – Hollywood MD
9:00pm – Myles Deep band – 219 Restaurant – Alexandria VA
9:00pm – Chris Dean & Matt Silkworth – Huntt’s Tavern – Pomfret MD
9:00pm – Sister Midnight – Twisted Bar & Grill – Hollywood MD
Sunday – August 31st
1:00pm – Monkey Business – Seabreeze Tiki Bar – Mechanicsville MD
1:00pm – Out of Order – Running Hare Winery – Prince Frederick MD
2:00pm – Pete Best – Wharf 38 – Deale MD
2:00pm – Blakbyrds – Wheel House Beer Garden – North Beach MD
2:00pm – Coastal Flats – Port of Leonardtown Winery – Leonardtown MD
2:00pm – John Luskey – Pirates Cove Dock Bar – Galesville MD
2:00pm – Alan Peather – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Sundown – Apehangers Bar & Grill – Bel Alton MD
2:00pm – David Murphy – Southern Trail Distillery – Mechanicsville MD
3:00pm – Wes Ryce – Potomac Speedway – Budds Creek MD
3:00pm – Joe Lewis Reggae – Coast 2 Coast Seafood Bar – Solomons MD
3:00pm – Port Tobacco Pickers – The Scuttlebutt – Cobb Island MD
3:00pm – Elena Barrett – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Richard Hayward – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Mike Mead & Eric Wolf – Traders Pub – Chesapeake Beach MD
3:00pm – The Reagan Years – The TIKI Bar – Solomons MD
3:00pm – Doc Lohn – The Pier – Solomons MD
4:00pm – Peter James – Happy Harbor Restaurant – Deale MD
6:00pm – Faith Noel – Bugeye Grill – Solomon MD
6:00pm – Myles Deep Band – Wheel House Beer Garden – North Beach MD
6:00pm – Bangerz Only – Seabreeze Tiki Bar – Mechanicsville MD
8:00pm – Never 2 Late – Toots Bar – Hollywood MD
Monday – September 1st – Labor Day
1:00pm – GrooveSpan Band – Pier 450 – Ridge MD
2:00pm – Jack Allen – Wharf 38 – Deale MD
2:00pm – 4th Wall Break – Seabreeze Tiki Bar – Mechanicsville MD
2:00pm – Kurt Scheslinger – PTL Winery – Leonardtown MD
3:00pm – Monkey Business – Stoney’s Clarkes Landing – Hollywood MD
3:00pm – The Whiskey Brothers – Happy Harbor Restaurant – Deale MD
3:00pm – John Luskey & Ryan Forrester – Dockside Sports Bar – Deale MD
3:00am – Byron Ciotter – Traders Seafood & Ale – Chesapeake Beach MD
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
7:00pm – Eclipse (Journey tribute) – Rod ‘N’ Reel – Chesapeake Beach MD
Tuesday – September 2nd
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – September 3rd
6:00pm – Justin Myles – The Pier – Solomons MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
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