Upcoming Chestertown Events

Festivals, arts, boating events, and other community happenings in the Chestertown area.

Saturdays, Year-Round – Chestertown Farmers Market – 8:00 a.m. until noon. Located on the 300 & 200 Block of High St.

May 24 – 26, 2024 – Chestertown Tea Party Festival – Annual festival centered around the reenactment of the 1774 tossing of tea cargo into the Chester River in protest of the British Parliament’s closing of the port of Boston. The festival includes Tea Toss Reenactment, Colonial Parade, street tarty, raft race, street performances, colonial crafts, strolling musicians, local fare, and more. Chestertown, MD.

November 1 – 3, 2024 – Schooner Sultana Downrigging Weekend Festival – One of the largest tall ship gatherings in North America – plus a bluegrass music festival. Tall Ship sails, tours, incredible live bluegrass music, lectures, exhibits, family activities, regional food and more. Held at Chestertown Marina.