Chestertown Events

September and October Events


Chestertown Farmers’ and Artists’ Marketchestertown1_fountain-park
Every Saturday , 8 a.m. – 12 p.m. at Fountain Park in the center of town

KidSPOT Children’s Creativity Center
Every Saturday, 9 a.m. – 12 p.m.chestertown2_downrigging_weekend
Open every Saturday free of charge to kids accompanied by an adult, KidSPOT provides an opportunity for children ages 2-12 to expand creative expression and creative problem solving.

Schooner Sultana Public Sail
Saturdays in September
Departing and returning from Sultana’s home port of historic Chestertown, two-hour public sails are a great way to sail the Chester River onboard a traditional schooner.

Chestertown Jazz Festival
September 12, 12 p.m.
Featuring national and regional jazz, playing something for everyone: straight ahead, Latin, smooth jazz, instrumentalists and vocalists. Local beer, wine and food available at the park.

Chestertown First Friday
The first Friday of every month, 5 p.m. – 9 p.m.
Visit Historic Chestertown, while enjoying extended shop hours and arts and entertainment throughout downtown.

chestertown4_silent maidChestertown Riverfest
September 26, 12 p.m. – 7:30 p.m.
The community event features the unveiling of a large, floating, solar-powered sculpture on the river, the 9th annual cardboard boat regatta, kayak and canoe races, a poker run, as well as live music, food and kids activities.

RiverArts 16th Annual Studio Tour
October 24-25 and October 31-November 1, 10 a.m. – 5 p.m.
This fascinating, free, self-guided journey will lead you to discover amazing work by artists, many of whom are known and recognized for their achievements throughout the art world.

Downrigging Weekend
October 30, 8 a.m.- November 1, 5 p.m.
Sultana’s Downrigging Weekend is one of the largest annual tall ship and wooden boat festivals on the East Coast. See more at public-programs/sultana-public-sails/downrigging-weekend- 2/#sthash.SXjmGocJ.dpuf. *

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