SOUTHERN MARYLAND — From live music and theater to community fairs and family festivals, this week’s calendar is filled with ways to get out and make memories. In Calvert County, kids and families can unleash their inner buccaneer at Pirate Day at the Calvert Marine Museum, complete with crafts, songs, and a chance to walk the plank. Across the region, Batman Day brings comic shop celebrations, cosplay contests, and movie marathons for fans of the Dark Knight. St. Mary’s County is complete with fairs, cultural events, and historic gatherings. Plus, Oktoberfest season has arrived — see the full guide here to plan where to raise a stein and join the festivities.
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THINGS TO DO IN CALVERT COUNTY
12 Angry Jurors by Twin Beach Players runs Sept. 19–Oct. 4, located at Boys & Girls Club, 9021 Dayton Avenue, North Beach, MD – The classic courtroom drama unfolds as twelve jurors deliberate the guilt of a teenager accused of murdering his father. Performances Fridays and Saturdays at 8 p.m., Sundays at 3 p.m. $18–$20 plus fees.
9th Annual North Beach American Film Festival on Sept. 20 (10 a.m. to 8 p.m.), located in North Beach, MD – A full day of independent cinema featuring documentaries, narratives, and visionary storytelling, including State Champions, Grandma’s Hands, America in the Dark, Sugar Beach, and Coffee with Golconda. Free admission (not suitable for children).
Village Days on Sept. 20 (10 a.m. to 3 p.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD – Step into Maryland’s past with demonstrations, activities, and historic village tours. Free admission.
Artsfest ’25 on Sept. 20–21 (10 a.m. to 5 p.m. each day), located at Annmarie Sculpture Garden & Arts Center, 13470 Dowell Road, Solomons, MD – Celebrate 33 years of Southern Maryland’s largest music and arts festival with over 40 live performers and 170+ artists. Enjoy food, beer, wine, and kids’ activities throughout the weekend. Tickets required.
Pirate Day on Sept. 20 (10 a.m. to 3 p.m.), located at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD – Dress like a pirate and enjoy crafts, toy boat building, tattoos, and walking the plank. Pirate songs at 12:30, 1:30, and 2:30 p.m. Included with museum admission (suggested $2 per toy boat).
“This Is Me” Color Run on Sept. 21 (8 a.m.), located at The Calverton School, 300 Calverton School Road, Huntingtown, MD – A colorful, family-friendly event with music, games, treats from the Novel Bakery, and community vibes. Early registrants received swag bags with sunglasses, a bandana, a bracelet, and a celebration color packet. Registration required.
Big Bingo Game on Sept. 21 (11 a.m.), located at Rod ‘N’ Reel Resort – The Overlook, 4150 Mears Ave., Chesapeake Beach, MD – Spend the day playing for cash prizes and enjoying an exciting atmosphere. Tickets are $40 and available at the door. Pre-order by Sept. 20 at 11:59 p.m. to receive a $10 meal voucher for CBQ. $40 admission.
STEAMLab Jr: Fireworks on Sept. 22 (6:30 to 7:30 p.m.), located at Twin Beaches Branch Library, 3819 Harbor Rd, Chesapeake Beach, MD – Kids in grades K–2 can explore STEAM topics by building, coding, counting, and creating in fun, hands-on activities. Free, registration required.
Free Trivia Night at CBQ on Sept. 24 (6:30 p.m.), located at CBQ, 4150 Mears Ave., Chesapeake Beach, MD – Test your wits with fun and quirky survey-style questions in a team trivia challenge. Bring friends, family, or co-workers for an evening of competition, laughter, and great food. CBQ favorites like pulled pork sandwiches, quesadillas, and signature cocktails will be available. Free, public event.
Calvert County Fair Sept. 25–28, located at Calvert County Fairgrounds, 140 Calvert Fair Drive, Prince Frederick, MD – A family favorite fair with carnival rides, food, games, livestock shows, educational exhibits, contests, and entertainment. Free daily admission except as specified in the schedule.
Capture the Flag & Flashlight Tag on Sept. 25 (7 to 8 p.m.), located at Chesapeake Hills Golf Course, 11352 H G Truman Rd, Lusby, MD – Kids ages 8–14 can join 30 minutes of capture the flag followed by 30 minutes of flashlight tag with glow sticks and flashlights. A fun evening of teamwork, bonding, and running in the dark. Free.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
September Comedy Night with Mr. K & Friends on Sept. 19 (8 to 11:30 p.m., doors 7 p.m.), located at Grace’s Event Center, 4045 Renner Road, Waldorf, MD – Laugh the night away with national headliners including Larry Lancaster, The Gwynn Factor, and Mr. K, plus music by DJ Ruii. Tickets required.
Airness at Port Tobacco Players running Sept. 19 through Oct. 5, located at Port Tobacco Players Theatre, 508 Charles St., La Plata, MD – Follow Nina’s hilarious and heartfelt journey into the world of competitive air guitar as she discovers the joy of music, friendship, and self-expression. Airness is a high-energy comedy with a rock-and-roll spirit and a reminder that everything we need to shred is already inside us. Tickets required.
Lowe’s Kids Workshop: Football Spirit Board on Sept. 20 (10 a.m. to 1 p.m.), located at Lowe’s Waldorf, 2525 Crain Highway, Waldorf, MD – Kids can build and decorate a Football Spirit Board with guidance from Lowe’s team members. Supplies are provided, but space is limited. Hurry—registration closes today. Free, registration required.
Southern Maryland House of Nerf 10-Year Anniversary Blaster Battle on Sept. 20 (11 a.m. to 5 p.m.), located at Charles County Fairgrounds and Event Center, 8440 Fairground Rd., La Plata, MD – Celebrate a decade of foam-flinging fun with the Southern Maryland House of Nerf. Enjoy all-day Nerf battles, community games, and family-friendly action in this milestone event. Admission details available through organizers.
The Magnolia Market on Sept. 20 (10 a.m. to 4 p.m.), located at Serenity Farm at Benedict, 6932 Serenity Farm Road, Benedict, MD – Enjoy a day of shopping, live music, and family fun at Serenity Farm’s annual Magnolia Market. The event features local vendors, food trucks, and activities for all ages, rain or shine. Free admission; $10 parking fee per vehicle.
Batman Day 2025 on Sept. 20, celebrated across Southern Maryland – Fans of the Dark Knight can enjoy all-day events at Third Eye Comics in Waldorf and Lexington Park with discounts, free Batman comics, and cosplay contests, plus a two-day Batman movie marathon at Xscape Theatres Brandywine 14 featuring The Lego Batman Movie, Batman Begins, The Dark Knight, and The Dark Knight Rises. Free comic shop events; $5 movie tickets.
Veteran Service Dog Memorial Project Kick Off on Sept. 20 (12:30 to 3 p.m.), located at the Maryland Veterans Museum at Patriot Park, 11000 Crain Highway, Newburg, MD – Celebrate the launch of America’s first memorial specifically dedicated to Veteran Service Dogs during National Service Dog Month. The project honors the bond between veterans and their service animals, highlighting their role in recovery and independence. Free, public event.
Benedict Day Celebration on Sept. 20 (beginning at 11 a.m.), located at Endeavor Point, 7890 Mill Creek Rd., Benedict, MD – Foods and drinks for purchase, exhibits from Camp Stanton, Benedict memorabilia, oyster cans, Calvert Drive In, and a moon bounce. Free admission.
Moonlight Movie Nights on Sept. 20 (at dusk), located at The Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – Wrap up the summer season with one last free outdoor movie night for the whole family. Bring your blankets and lawn chairs for a cozy evening under the stars watching Garfield the Movie. Free admission.
Christopher J. Wright Memorial Car Show on Sept. 21 (registration 9 a.m. to noon, awards at 2 p.m.), located at Newburg Volunteer Rescue Squad & Fire Department, 12245 Rock Point Road, Newburg, MD – All years, makes, models, and motorcycles welcome. Features include door prizes, food, music, 50/50 raffle, vendors, and awards for Top 50, Top 3 Motorcycles, Special Class, and Best in Show. Free admission for spectators; $25 entry fee for participants. $25 entry fee (cars/motorcycles).
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
St. Mary’s County Fair 2025 on Sept. 19–21, located at St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD – Celebrate 78 years of agriculture and community with exhibits, rides, parades, livestock shows, auctions, food, and family fun. Wristband Day offers unlimited rides. $10 adults, $2 children ages 3–11, free under 3.
Lowe’s Kids Workshop: Football Spirit Board on Sept. 20 (10 a.m. to 1 p.m.), located at Lowe’s California, 45075 Worth Ave., California, MD – Kids can build and decorate a Football Spirit Board with guidance from Lowe’s team members. Supplies are provided, but space is limited. Hurry—registration closes today. Free, registration required.
Ceremony of Return – Reinterment at the Brick Chapel on Sept. 20 (10 a.m.), located at Historic St. Mary’s City, 18751 Hogaboom Lane, St. Mary’s City, MD – A solemn and historic event reinterring early Maryland colonial remains uncovered during archaeological work at the Brick Chapel. The procession begins at the State House at 10 a.m., followed by remarks, the reinterment, and a light reception. Free and open to the public; seating limited in chapel, live-stream viewing tent available.
Quiet Birding: A Backyard Get-Together About Birds on Sept. 20 (9 to 11 a.m.), located in Wildewood, California, MD – Hosted by Jan de Regt, this no-walking, coffee-in-hand program is ideal for beginners and includes an introduction to using the Merlin Bird ID app. Free admission. Join the Audubon Society to support bird conservation in our region.
Drayden African American Schoolhouse Open House on Sept. 20 (11 a.m. to 2 p.m.), located at 18287 Cherryfield Road, Drayden, MD – Tour one of the nation’s best-preserved one-room African American schoolhouses and learn about its history and importance to education in St. Mary’s County. Staff will be on site to answer questions and provide information. Free, public event.
4th Annual Walk for Recovery on Sept. 20 (9 a.m.), located at Leonardtown Square, Leonardtown, MD – A free, family-friendly event to celebrate and support those in recovery. Attendees receive a t-shirt and water bottle (while supplies last) and can connect with recovery resources. Activities include DJ Recovery, poetry, lawn games, giveaways, Narcan training, rock painting, face painting, and peer support. Free, public event.
Birding the Fields and Trails of Historic Sotterley on Sept. 20 (9 a.m.), located at Historic Sotterley, 44300 Sotterley Ln., Hollywood, MD – Explore Sotterley’s scenic trails and river views while spotting Bald Eagles, songbirds, meadowlarks, sparrows, and more. All levels of birdwatchers welcome. Bring binoculars if you have them, wear comfortable shoes, and dress for the weather. Free, public event.
Maryland Dove Passenger Sail on Sept. 21 (10 a.m. to noon), located at Historic St. Mary’s City, 47414 Old State House Road, St. Mary’s City, MD – Experience a rare opportunity to sail on board the Maryland Dove, a spectacular wooden vessel. Minimum age to sail is 5 years old. $60 general admission / $50 HSMC members.
Lunchtöberfest – Bavarian-Style Luncheon with Rob Young on Sept. 25 (11 a.m. to 12:15 p.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Celebrate Oktoberfest with festive live music from Rob Young and a Bavarian-style lunch featuring bratwursts, potato salad, spiced apples, 3-bean salad, and fresh fruit. Advance registration is required. $7 for those under 60; donation for 60 and older.
Raíces Negras – Latin American Heritage Month Concert on Sept. 25 (4:30 to 6 p.m.), located at Carver Recreation Center, 7382 Lincoln Ave., Lexington Park, MD – Enjoy a free performance by Raíces Negras, a 12-piece ensemble led by Dr. Ceylon Mitchell. The group blends Afro-Brazilian, Afro-Cuban, and Latin American chamber music traditions for a unique cultural celebration. Free, public event.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – September 19th
4:00pm – Jack Allen – Island Music Company – La Plata MD
4:00pm – Highway Ramblers – JaneMark Vineyard – Brandywine MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Dillon Bodiford – Barefoot Farms – Avenue MD
5:00pm – WIP Acoustic – Greene Turtle Sports Bar – California MD
5:00pm – Richard Hayward – Greene Turtle Sports Bar – La Plata MD
5:30pm – Monkey Business – Running Hare Vineyard – Prince Frederick MD
6:00pm – Nightcap – Creekside Farm Brewery – King George VA
6:00pm – David Norris & Stu – Coast 2 Coast – Solomons MD
6:00pm – Byron Ciotter – The Local – Hollywood MD
6:00pm – Hyland Brothers – Happy Harbor Restaurant – Deale MD
6:00pm – Dead Flowers – Wheel House Beer Garden – North Beach MD
6:00pm – Joe Parsons – Southern Trail Distillery – Mechanicsville MD
6:00pm – Sister Midnight – Kellam’s Field – Chesapeake Beach MD
6:00pm – Funkzilla – The TIKI Bar – Solomons MD
6:00pm – Doc Lohn – Dockside Restaurant & Sports Bar – Deale MD
6:30pm – Steve Potter Band – Town Hall Series – La Plata MD
7:00pm – Billy Breslin – Ruddy Duck Brewery & Grill – Solomons MD
7:00pm – John Luskey – Pirate’s Cove Dock Bar – Galesville MD
7:00pm – Run Catch Rain – O’Gannigan’s Irish Pub – Prince Frederick MD
8:00pm – Ephitol – Toots Bar – Hollywood MD
8:00pm – Hinder / Robert’s Revenge – The Rex Theatre – Leonardtown MD
8:30pm – Dead Eye Stare – Ollie’s Bar & Grill – La Plata MD
Saturday – September 20th
12:00pm – Jason Mitchell – Magnolia Market @ Serenity Farm – Benedict MD
12:00pm – Lookout Band – ArtsFest @ Annemarie Gardens – Solomons MD
1:00pm – Kelly Micheala – ArtsFest @ Annemarie Gardens – Solomons MD
1:00pm – Shane Graham – Xella Winery & Vineyard – Laurel Grove MD
2:00pm – Swamp Weasels – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Dust on the Bottle – Corteau Vineyards – Mechanicsville MD
2:00pm – Michael Ferro – Ketch 22 Restaurant – North Beach MD
2:00pm – GrooveSpan – Perigeaux Vineyards & Winery – Saint Leonard MD
2:00pm – High Energy Group – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – The Bootleggers – ArtsFest @ Annemarie Gardens – Solomons MD
3:00pm – Waters Edge Band – Apehangers Bar & Grill – Bel Alton MD
5:00pm – Joseph Norris – Morris Point Restaurant – Abell MD
5:00pm – Whiskey Brothers – American Legion #206 – Chesapeake Beach MD
6:00pm – Red Jam – Seabreeze Tiki Bar – Mechanicsville MD
6:00pm – Loose Change – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Monkey Business – Stoney’s Clarles Landing – Hollywood MD
6:00pm – Midnight Sunsets – Wheel House Beer Garden – North Beach MD
6:00pm – Jack Allen – Barely Naked Brewing – Stafford VA
6:00pm – Chris Dean – The Local – Hollywood MD
6:00pm – Nightcap – Southern Trail Distillery – Mechanicsville MD
7:00pm – Rise Band & Show – Blue Fish Pub – Solomons MD
7:00pm – Girl Crush – Dockside Tiki Bar – Colonial Beach VA
7:00pm – 4th Wall Break – Pax River Ale House – Lexington Park MD
7:00pm – Chris Turner – The Brass Tap – California MD
7:00pm – The Blair Ritch Project – The Potomac Gardens – Coltons Point MD
7:00pm – South Creek w/Donald Quade – Back Road Inn – Leonardtown MD
8:00pm – The Basement Snakes – Buckets Bar & Grill – Lusby MD
8:00pm – Framing the Tin Man – Toots Bar – Hollywood MD
8:30pm – Mike Newberry & the Availables – Ollie’s Bar & Grill – La Plata MD
9:00pm – Brian Grilli – Apehangers Bar & Grill – Bel Alton MD
9:00pm – Tommy McGee Band – Huntt’s Tavern – Pomfret MD
9:00pm – Dillon Bodiford – Betty Russell’s Store & Bar – Valley Lee MD
Sunday – September 21st
11:00am – SOMD Jazz Trio Jonah Orevillo – Pier 450 – Ridge MD
11:00am – The Friskies – Blue Fish Pub – Solomons MD
2:00pm – John Luskey – Wharf 38 – Deale MD
2:00pm – Shortcut Sunny – Robin Hill Farm & Vineyard – Brandywine MD
2:00pm – Swingaway Jazz – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Monkey Business – Apehangers Bar & Grill – Bel Alton MD
3:00pm – Audra & Johnny – Dockside Restaurant & Sports Bar – Deale MD
3:00pm – Girl Crush Acoustic – The Boathouse @ Anchored Inn – Deale MD
3:00pm – Billy Breslin – Pirates Cove Dock Bar – Galesville MD
3:00pm – Richard Wayward – Happy Harbor Restaurant – Deale MD
3:00pm – Doc Lohn – Wheel House Beer Garden – North Beach MD
3:00pm – Funkzilla Unplugged – The Pier – Solomons MD
4:00pm – Steve Potter Band – PTR Waterfront – Port Tobacco MD
Monday – September 22nd
7:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – September 23rd
5:00pm – Michael Ferro – Heritage 485 – Prince Frederick MD
6:30pm – Wes Ryce – Apehangers Bar & Grill – Bel Alton MD
6:30pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – September 24th
5:00pm – Pete Best – The Boathouse @ Anchored Inn – Deale MD
6:00pm – Nightcap – 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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