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
Whalen Commons 19701 Fisher Avenue, Poolesville
Annual Fall Festival featuring live music, local breweries, and plenty of kids activities!
Free
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Mark your calendars for this weekend at the Beer Farm, where Mike Heuer will take the stage with his unique blend of Alt/Folk-Pop! With 14 years of experience as a…
Bayhead Park 1661 Bay Head Rd, Annapolis
SpookyFest brings back your absolute favorite traditions alongside brand-new, upgraded experiences the whole crew will love. Your favorite Fall Festival classics—like the Haunted House, Halloween movies in the theatre, and…
$11 – $27
New Germany State Park 349 Headquarters Lane, Grantsville
Celebrate the season by completing the Trick-or-Treat Trail for kids age 12 and under, or a Haunted Hike spooky adventure. Trick or Treat Trail for ages 12 and under. 5-6:30 p.m.…
Free
Dance like it’s 1776 to lovely live music as was done throughout the American colonies, including right here in Annapolis. Dances are held the 3rd Saturday of each month at…
$5 – $15
Annapolis Friends Meetinghouse 351 Duboise Rd., Annapolis, 21401, United States
Dance like it’s 1776 to lovely live music as was done throughout the American colonies, including right here in Annapolis. Dances are held the 3rd Saturday of each month at…
$5 – $15
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
Maryland Avenue Annapolis Maryland Ave and State Circle, Annapolis, Maryland 21401
Entertainment, food, demonstrations and shopping along Maryland Avenue.
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
Carroll Creek Linear Park Frederick
Join us for a day of family fun and community spirit! Live Music, Handmade Goods & Local Art. Delicious Food, Treats & More Free Kids’ Activities like twisted balloons and…
Free
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