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
B.I.G. Warehouse 451 Defense Highway, Annapolis
Books for International Goodwill (BIG) invites you to join us for our book sales. Thanks to generous donations, we have many new titles to choose from in all categories. Discover…
Free
Beer Farm @ Homestead Gardens 743 West Central Avenue, Davidsonville, MD 21035, United States
Michael McHenry, a seasoned artist, injects his performances with a unique blend of soulful, sexy, and psychedelic funk-rock. His profound love for music is evident in every note he plays.…
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
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
Maryland Hall 801 Chase Street, Annapolis, Maryland 21401, United States
A captivating tale of love and the supernatural with the Ballet Theatre of Maryland. Be transported to the rugged hills and misty skies of the Scottish Highlands in this quintessential…
$36 – $62
2002 Annapolis Mall Rd Annapolis, MD 21401 United States
Helen Hayes Award Recommendation for the Compass Rose production, a magical, fun musical for the whole family, following the antics of Charlie Brown and the Peanuts. Running until Oct 18.
$15 – $55
The Byzantium Event and Conference Center 2747 Riva Road, Annapolis, MD 21401, United States
Join Lace ‘Em Up for Libby for an evening themed with flannel and jeans to support the fight against childhood cancer. Swamp Donkey NewGrass will be providing the music so…
B.I.G. Warehouse 451 Defense Highway, Annapolis
Books for International Goodwill (BIG) invites you to join us for our book sales. Thanks to generous donations, we have many new titles to choose from in all categories. Discover…
Free
CovingtonAlsina, 67 West St #200, Annapolis, MD 21401, USA West Street 67, Annapolis, Maryland 21401, United States
Join us for a fun, hands-on workshop that teaches kids how to make and manage money. We’ll discuss the four things you can do with your money: Save, spend, give,…
$25
600 Quite Park Road, Annapolis, MD 21403 600 Quiet Waters Park Road, Annapolis, 21403, United States
The Friends of Quiet Waters are hosting the 36th annual Art @ the Park fine arts festival on October 17th and 18th from 10:00am until 4:00pm each day. The Park…
$8.00
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’…
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
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