Hawkins Road Trailhead, Bacon Ridge Natural Area, Crownsville
Protect the Health of YOUR Local Forest: Join us at Bacon Ridge Natural Area in Crownsville to spend a morning removing harmful invasive plants from along the trails! Scenic Rivers’…
Free
Bacon Ridge Natural Area 1555 Severn Chapel Road, Crownsville
Protect the Health of YOUR Local Forest: Join us at Bacon Ridge Natural Area in Crownsville to spend a morning removing harmful invasive plants from along the trails! Scenic Rivers’…
Annapolis City Dock Dock Street, Annapolis, Maryland 21401
Walk the floating docks during the Annapolis Sailboat Show, climb aboard gleaming yachts and center consoles, and explore everything from family cruisers to weekend fishing rigs. Whether you’re boat-curious, shopping…
$10 – $32
Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, Maryland 21403
Enjoy live music, an outstanding display of art, including ceramics, woodworking, jewelry, and painting, along with demonstrations and a variety of food trucks. There will be art activities for young…
$8
Oxon Hill Farm 6710 Oxon Hill Rd, Oxen Hill
As the temperature drops and the leaves start to change, join us for the Oxon Hill Farm Fall Festival – live music, sheep dog demonstrations, pumpkin painting, and a Community Showcase…
Free
Tilghman Island 5979 Tilghman Island Rd, Tilghman
Live music, Crab-picking, oyster-shucking, and boat-docking contests. Fresh seafood along with other food.
Free
St. Mary’s County Fairgrounds 42455 Fairgrounds Road, Leonardtown
US National Oyster Shucking Championship, Tasting Tent, Stories from a Mermaid, educational exhibits, live performances.
$50
Captain Avery Museum 1418 East West Shady Side Road, Shady Side, Maryland 20764
Captain Avery Museum Oyster Festival October 17th 11:00 am- 5:30 pm Raindate: October 18th Tickets are now on sale for the Captain Avery Museum 2026 Oyster Festival! Join us on…
$10 – $20
Captain Avery Museum 1418 East West Shady Side Road, Shady Side, Maryland 20764
Join Captain Avery Museum at their Oyster Festival! This event features good community company, fine regional music, an array of choice gifts for purchase, a cash raffle, local food and…
$10 – $20
Downtown Berlin Bay Street & Stephen Decatur Park, Berlin
Authentic Oktoberfest music featuring the Lost Lederhosen Band and the Dunehounds. A variety of OKTOBERFEST food featuring brats and knockwurst, pretzels, German chocolate cake, pie, ice cream, smoothies & more!…
Free
Rockville Civic Center Park 603 Edmonston Drive, Rockville
From Packard to Ferrari, the Rockville Antique and Classic Car Show showcases 33 car clubs, bringing together auto collectors and enthusiasts to share memories of classic cars from years past.…
Free
Patuxent River Park 16000 Croom Airport Road, Upper Marlboro
The American Indian Festival is a vibrant celebration of Native American culture, heritage, and traditions, offering live music and traditional and contemporary dances of Native America. DIY arts and crafts…
Free
Schifferstadt Architectural Museum 1110 Rosemont Ave, Frederick
Come enjoy great food and drink, lively German music, historic demonstrations, museum tours, and handmade products from many arts & crafts vendors. Our biggest event of the year!
Free
Patuxent River Park 16000 Croom Airport Road, Upper Marlboro
Celebrate Native American culture at the 18th Annual American Indian Festival, featuring traditional music, dance, crafts, food, storytelling, and family-friendly activities.
Free
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Doug Segree brings more than 30 years of live performance experience to the Beer Farm, blending acoustic, rock, pop, and classic favorites into an engaging set built around strong vocals,…
Pier 4 Marina 301 Fourth St, Annapolis, 21403, United States
What do Dragon Boats, breast cancer survivors, and Spa Creek have in common? DragonFest 2026, the annual fundraiser for the Annapolis Dragon Boat Club! Come out to Pier 4 in…
Free
Union Market 1309 5th St NE, Washington, DC
Introducing the DC Wine Fest®, a wine tasting experience that aims to stimulate all of your senses. Your ticket includes all wine tastings.
$61.64
Kinder Farm Park 1001 Kinder Farm Park Road, Millersville, Maryland
Fall Fun and entertainment over two weekends. Scarecrow-making, hayrides, farm animals, family games, and trunk-or-treat. Fee for some activities Saturday, October 17, 2026 From 12:00 PM to 3:00 PM Online…
Free – $11.20
CovingtonAlsina, 67 West St #200, Annapolis, MD 21401, USA West Street 67, Annapolis, Maryland 21401, United States
This workshop is designed to help middle school students (ages 12-14) make educated financial decisions as they enter into the next phase of life. We’ll talk about how to manage…
$25
Maryland Zoo One Safari Place, Baltimore
Kick off the weekend with a lively Friday night at OktoBEAR-Eve—an exclusive 21+ event featuring seasonal brews, festive vibes, and wild encounters (leave the cubs at home for this one).…
$35 – $85
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