October 1 - 21. Free Fall Baltimore. A free, city-wide arts extravaganza throughout the month of October. More than 300 free events, including music, art, dance, history, theater, and hands-on workshops. More info.
October 19. Annmarie After Hours. A casual adult evening at Annmarie Gardens and Arts Center. Enjoy art, wine and beer, and light hors d'oeuvres. More info. Solomons Island, MD.
October 19 & 20. Chestertown Wildlife Exhibition and Sale. Carvers, painters, photographers, and artists exhibit throughout town. Duck and goose calling competition, sportsman's pavilion, Shucker's Ball, Demonstrations, regional foods, beer and wine tasting, music. More info. Chestertown, MD.
October 19 & 20. Upper Bay Museum Decoy Show. Held at the North East Fire Hall on Mauldin Ave. Decoy show, demonstrations, auction. More info. North East, MD
October 19 - 21. Academy Art Museum Craft Show. Showcasing fine crafts from more than 60 national artists. Located in the Academy Art Museum and the Waterfowl Building. More info. Easton, MD.
October 20. Easton's Farmers Market. Every Saturday through mid December. 8:00am to 1:00pm. Harrison Street Public Parking Lot.More info. Easton, MD.
October 20. Bark in the Park. Easton, MD, dog walk, fun dog show, 10K race and 5k fun run/walk, plus other activities and food. A fundraising event for Talbot Humane. More info. Easton, MD.
October 20. Olde Towne Portsmouth Farmer's Market. 9:00am to 1:00pm. In the historic district, just outside the Portsmouth Art & Cultural Center Courtyard at Court and High Streets. More info. Portsmouth, VA.
October 20. Havre de Grace Fall Art Walk. 11:00am to 6:00pm. Combine walking for exercise and enjoying art around town. Stop by participating businesses to get your Art Walk flyer stamped for a chance to win prizes. There will be music, art demonstrations, and sales along the route. More info. Havre de Grace, MD.
October 20. Tilghman Day. Oyster shucking an crab picking contests, crab skiff races, docking contest, and more. More info. Tilghman Island, MD
October 20 & 21. Fall into St Michaels. Scarecrow competition, pumpkin carving competition, 5k Walk/Run, Ghost Tours, Jack Russell Races, Parade. More info. St. Michaels, MD.
October 20 -21. Cambridge Schooner Rendezvous. Schooners and other historic vessels gather at Cambridge's Long Wharf Park. Festivities include sails, entertainment and food. More info. Cambridge, MD.
October 20 - 21. St Mary's County Oyster Festival. Features the National Oyster Shucking and National Oyster Cook-Off competitions. Live entertainment, seafood, rides and games. Held at the St. Mary's County Fairgrounds in Leonardtown, MD. More info.
October 20 - 21. Town Point Virginia Wine Festival. This annual festival features over 200 Virginia wine varieties. More info. Norfolk, VA.
October 21. Oyster Festival at Captain Avery Museum. Food, live music, craft vendors, exhibits, activities for the kids. Shady Side, MD. More info.
