SOUTHERN MARYLAND — Southern Maryland’s upcoming week is filled with community favorites, from a grand opening offering free bagels to the first 50 customers to holiday craft fairs, early Santa appearances, festive workshops and seasonal performances. The community can explore holiday bazaars, enjoy live shows, or unwind at a cozy “paws and popcorn” movie night, take part in a Toys for Tots Toy Drive at Solomons Inn, filled with food, games, and family fun. With creative, charitable and outdoor activities rounding out the week, there’s no shortage of ways to plan ahead in Southern Maryland.
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THINGS TO DO IN CALVERT COUNTY
Pink Friday Solomons – Calvert Marine Museum Store & Participating Solomons Shops on Nov. 21 (all day), located at Participating Shops Throughout Solomons, Solomons, MD – A community-focused shopping day inviting visitors to explore local businesses, enjoy special promotions and support Solomons merchants ahead of Black Friday. Free admission.
Campfire on the Beach on Nov. 21 (5:30 to 7 p.m.), located at 9023 Bay Avenue, North Beach, MD – Enjoy a cozy beach campfire with treats, warm beverages and nearby local shops offering unique seasonal finds. Free admission.
Toys for Tots Toy Drive on Nov. 21 (6 to 9 p.m.), located at Solomons Inn Resort & Marina, 155 Holiday Drive, Solomons, MD – Enjoy a complimentary buffet, games and giveaways while donating new, unwrapped toys to support Toys for Tots. Free admission.
Wine and Line Dancing on Nov. 21 (6 to 10 p.m.), located at Running Hare Vineyard, 150 Adelina Road, Prince Frederick, MD – Enjoy an evening of wine and line dancing led by instructor Carole Clark for dancers of all experience levels. Ticket required.
Ultimate Day of Live Boxing in Prince Frederick on Nov. 22 (3 p.m.), located at 2400 Solomons Island Road South, Prince Frederick, MD – Enjoy a full card of amateur boxing bouts and a special appearance by former world champion Demarcus “Chop Chop” Corley. Ticket required.
Holiday Bazaar on Nov. 22 (9 a.m. to 3 p.m.), located at American Legion Stallings-Williams Post 206, 3330 Chesapeake Beach Road, Chesapeake Beach, MD – Enjoy baked goods, raffles, kids’ crafts and local vendors, with food available for purchase and a visit from Santa. Free admission.
OLSS Christmas Bazaar on Nov. 22 (9 a.m. to 2 p.m.), located at 90 Alexander Lane, Solomons, MD – Enjoy a festive bazaar featuring vendors, crafters, a yard sale, concessions, a bake sale, a silent auction and a visit from Santa. Free admission.
Nautical Christmas Card Workshop on Nov. 24 (1 to 3 p.m.), located at Kocen Arts Center, 22 Duke Street, Prince Frederick, MD – Create festive nautical-themed watercolor art with provided supplies in a guided workshop for ages 12 and up. Ticket required.
Parent’s Morning Out on Nov. 26 (9 a.m. to 2 p.m.), located at Mt. Hope Community Center, 104 Pushaw Station Road, Sunderland, MD – Parents can drop off children ages 4–12 for supervised activities while they enjoy kid-free time to prepare for the holidays. Ticket required.
Thanksgiving Turkey Trot 5K on Nov. 27 (7 a.m.), located at Jefferson Patterson Park & Museum, 10515 Mackall Road, St. Leonard, MD – A family-friendly holiday run inviting the community to “strut their stuffing” while supporting Project ECHO and Jefferson Patterson Park & Museum. Ticket required.
For more Calvert County events, visit the Calvert County Maryland website.
THINGS TO DO IN CHARLES COUNTY
Audi Club at MIR – Four Rings, Full Send on Nov. 21 (9 a.m. to 5 p.m.), located at Maryland International Raceway, 27861 Budds Creek Road, Mechanicsville, MD – Audi owners can enjoy a full-day drag strip experience with open runs, safety meetings and pro-grade timing in this enthusiast-focused track event. Ticket required.
Thomas Stone High School – The Con by Tracy Wells on Nov. 21–22 (6:30 p.m.), at Thomas Stone High School, 3785 Leonardtown Road, Waldorf, MD – A suspenseful story of deception, intrigue, and clever twists. Tickets available through CCPS school sites.
Joseph and the Amazing Technicolor Dreamcoat on Nov. 21–23 (Nov. 21 at 8 p.m., Nov. 22 at 8 p.m., Nov. 23 at 3 p.m.), located at Port Tobacco Players Theater, 508 Charles Street, La Plata, MD – The Port Tobacco Players present a community musical retelling the story of Joseph with vibrant songs and colorful staging. Ticket required.
North Point High School – Peter and the Starcatcher on Nov. 21–22 (7 p.m.), at North Point High School, 2500 Davis Road, Waldorf, MD – The imaginative prequel to Peter Pan reveals how an orphan boy became a legend. Tickets available through CCPS school sites.
Westlake High School – The Bugs on Nov. 21–22 (7 p.m.), at Westlake High School, 3300 Middletown Road, Waldorf, MD – A quirky comedy exploring teamwork and transformation through the eyes of insects. Tickets available through CCPS school sites.
LifeStyles Walk to End Homelessness on Nov. 22 (9 a.m. to noon), located at La Plata Town Hall, 305 Queen Anne Street, La Plata, MD – Join LifeStyles of Maryland for a community walk supporting housing stability and raising awareness for neighbors experiencing homelessness. Ticket required.
2025 Indian Head Turkey Trot 5K & 10K on Sat. Nov. 22 (7:30–10:30 a.m.), at Indian Head Rail Trail, 10410 Theodore Green Blvd, White Plains, MD – Flat, scenic 5K and 10K courses along the Indian Head Rail Trail with optional virtual race, finisher’s medal, event shirt, and chip timing; benefits Lovepaws. Registration required.
NCAC’s 6th Annual Giving Fair on Nov. 22 (10 a.m. to 1 p.m.), located at Grace Lutheran Church and School, 1200 Charles Street, La Plata, MD – Kids rotate through craft stations to create handmade gifts with local artisans, with additional activities including face painting and a hot chocolate bar. Free admission.
St. Charles High School – Harry Potter and the Cursed Child (High School Edition) on Nov. 21–22 (7 p.m.) and Nov. 23 (2 p.m.), at St. Charles High School, 5305 Piney Church Road, Waldorf, MD – Return to Hogwarts with the next generation of wizards in this spellbinding two-part adaptation. Tickets available through CCPS school sites.
Holiday Market with Santa & Craft Vendors on Nov. 22 (9 a.m. to 2 p.m.), located at Benedict Fire Department, 18210 Hyatt Avenue, Benedict, MD – Enjoy holiday shopping with unique craft vendors, Santa photo opportunities and festive seasonal treats. Free admission.
Shutdown Support Food Relief Distribution on Nov. 23 (10 a.m. to 1 p.m.), located at American Legion Post 82, 101 Catalpa Drive, La Plata, MD – A drive-through food distribution for active-duty military, veterans and federal workers, offered in partnership with LifeStyles of Maryland while supplies last. Free admission.
Rochambeau Reception on Nov. 23 (3 to 5 p.m.), located at Maryland Veterans Museum at Patriot Park, 11000 Crain Highway, Newburg, MD – Celebrate the 250th Anniversary Victory Towns with march, music and memory along the Revolutionary Route to Victory, including a special appearance by Dr. Iris de Rode of the Ken Burns PBS documentary American Revolution. Free admission.
For more Charles County events, visit the Charles County Maryland website.
THINGS TO DO IN ST. MARY’S COUNTY
Bunco! on Nov. 21 (12:30 to 3:30 p.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Enjoy an afternoon of Bunco with chances to win prize money and socialize with fellow players. Ticket required.
Paws & Popcorn Night at Meow Dyer Cat Cafe on Nov. 21 (6 to 8 p.m.), located at Meow Dyer Cat Cafe, 41665 Fenwick Street #13, Leonardtown, MD – Enjoy two hours of cat lounge time, popcorn, drinks and a family-friendly movie during a cozy Thanksgiving-themed night. Ticket required.
Farndale Avenue Housing Estate Townswomen’s Guild Dramatic Society’s Production of A Christmas Carol on Nov. 21 (8 p.m.), located at Three Notch Theatre, 21744 South Coral Drive, Lexington Park, MD – A comedic twist on Dickens’ classic, this production features lively characters, audience participation and festive theatrical chaos. Ticket required.
Boone’s Bagels Grand Opening on Sat. Nov. 22 (time not listed), at Boone’s Bagels, 41654 Fenwick Street, Leonardtown, MD – Celebrate the grand opening with free bagels for the first 50 customers at this new local bagel shop. Free admission.
FCTC SkillsUSA Fall Festival on Nov. 22 (10 a.m. to 3 p.m.), located at Dr. James A. Forrest Career and Technology Center, 24005 Point Lookout Road, Leonardtown, MD – The SkillsUSA chapter hosts a fall festival featuring vendors, a car show and program information. Free admission.
Craft Fair on Nov. 22 (5 p.m.), located at Swords and Spoons, 22599 MacArthur Blvd Suite 126, California, MD – Browse handmade goods and seasonal items from local crafters. Free admission.
Sip and Flow Saturdays: Friendsgiving at Copper Compass Craft Distillery on Nov. 22 (11 a.m. to 1 p.m.), located at 4317 Charles Crossing Drive, White Plains, MD – Enjoy a 50-minute mat Pilates session followed by a sound bath and curated drink in a wellness-focused social experience. Ticket required.
Thanksgiving Centerpiece Workshop on Nov. 22 (10 a.m. to noon), located at 22720 Duke Street, Leonardtown, MD – Create a festive floral centerpiece using provided tools, materials, fresh flowers and a pumpkin base, with hot apple cider and a cookie included. Ticket required.
Turkey Trot 5K on Nov. 23 (9 a.m.), located at Lexington Manor Passive Park, 21675 South Coral Drive, Lexington Park, MD – St. Mary’s County Recreation and Parks hosts its annual 5K run and walk to support the youth scholarship fund. Ticket/admission info: registration required.
Fall Craft Fair on Nov. 23 (10 a.m. to 3 p.m.), located at 24801 Three Notch Road, Hollywood, MD – Browse seasonal crafts, enjoy lunch options including stuffed ham and visit the bake sale table hosted by the Ladies Auxiliary of the Hollywood Volunteer Fire Department. Free admission.
Southern Maryland History in Story & Song, with Joe Norris on Nov. 25 (10 to 11 a.m.), located at Northern Senior Activity Center, 29655 Charlotte Hall Road, Charlotte Hall, MD – Enjoy a sponsored performance featuring original songs and stories about Native American history in Southern Maryland. Free admission.
SOUTHERN MARYLAND LIVE MUSIC SCHEDULE BROUGHT TO YOU BY LYNN’S MUSIC LISTINGS
Friday – November 21st
5:00pm – Chris Dean – Greene Turtle Sports Bar – La Plata MD
5:00pm – Doc Lohn – Greene Turtle Sports Bar – California MD
5:00pm – Dust on the Bottle – Mully’s Brewery – Prince Frederick MD
5:00pm – Jack Allen – The Slice House – Leonardtown MD
6:00pm – Jayce Gallagher – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – HydraFX – Wheel House Beer Garden – North Beach MD
7:00pm – Justin Myles – Ruddy Duck Brewery & Grill – Solomons MD
7:00pm – Shane Graham – O’Gannigan’s Irish Pub – Prince Frederick MD
7:30pm – John Luskey – Pirates Cove Dock Bar – Galesville MD
8:00pm – Tommy McGee Band – Toots Bar – Hollywood MD
8:00pm – Nightcap Trio – Action Lounge & Billiards – Leonardtown MD
Saturday – November 22nd
12:30pm – Marianne Styles – Two Lions Vineyard – Upper Marlboro MD
1:00pm – Hyland Brothers – Running Hare Winery – Prince Frederick MD
2:00pm – Doc Lohn – Port of Leonardtown Winery – Leonardtown MD
2:00pm – Alan Prather – Robin Hill Farm & Vineyards – Brandywine MD
5:00pm – Monkey Business – PTR Waterfront – Port Tobacco MD
6:00pm – Rayon Walker – Dockside Restaurant & Sports Bar – Deale MD
6:00pm – Chris Dean – The Local – Hollywood MD
6:00pm – Byron Ciotter – Pax River Ale House – Lexington Park MD
6:00pm – Never 2 Late – Wheel House Beer Garden – North Beach MD
7:00pm – Shane Graham – The Brass Tap – California MD
7:00pm – The Basement Snakes – O’Gannigan’s Pub – Prince Frederick MD
8:00pm – Women of Country tribute – The Rex Theatre – Leonardtown MD
8:00pm – Hate The Toy – Toots Bar – Hollywood MD
8:00pm – Sister Midnight – The Tavern – Saint Leonard MD
8:00pm – The Mike Mead Band – Buckets Bar & Gril – Lusby MD
8:00pm – HydraFX – Cryer’s Back Road Inn – Leonardtown MD
8:30pm – Blazin’ Keys Dueling Pianos – Taphouse 1637 – California MD
8:30pm – Yani – Ollie’s Bar & Grill – La Plata MD
9:00pm – Steve Potter Band – Huntt’s Tavern – Pomfret MD
9:00pm – Justin Taylor Band – Apehangers Bar & Grill – Bel Alton MD
Sunday – November 23rd
1:00pm – Run Catch Rain – Running Hare Winery – Prince Frederick MD
2:00pm – Funkzilla Unplugged – POL Winery – Leonardtown MD
3:00pm – Catey Peters – Pirates Cove Dock Bar – Galesville MD
Monday – November 24th
6:00pm – Open Mic w/ Will Benthal – Toots Bar – Hollywood MD
Tuesday – November 25th
7:00pm – Open Mic w/Mike Trujillo – Twisted Bar & Grill – Hollywood MD
Wednesday – November 26th – Thanksgiving Eve
2:00pm – Joseph Norris – Port of Leonardtown Winery – Leonardtown MD
4:00pm – Blake & Hamner – Southern Trail Distillery – Mechanicsville MD
5:00pm – Madisun Bailey – Ketch 22 Restaurant – North Beach MD
5:30pm – Mike Heuer – Baia Coastal Kitchen – Chesapeake Beach MD
5:30pm – Funkzilla – Ruddy Duck Brewery & Grill – Solomons MD
6:00pm – Ben Heemstra – Brick Wood Fired Bistro – Prince Frederick MD
7:00pm – Open Mic w/Steve Nelson – The Tavern – Saint Leonard MD
8:00pm – Franklin Square – Apehangers Bar & Grill – Bel Alton MD
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