Shortly after WWII, at the request of The American Artists' Professional League in New York City, their board member, Gretchen Wood Call, was asked to form a chapter on the Eastern Shore of Maryland. Thus, in 1946, the Chestertown Arts League was born with Mrs. Call serving as its first President.
In the early years members met in the homes of its members. As the membership grew the League met at the Washington College Alumni House, the Old Railroad Station, the Parish Hall of Emmanuel Church, the Public Library, and the Townshend Building. In November, 1987, The Arts League moved to 204 Cannon Street in Chestertown. In September, 2000 The Arts League moved to its current facility at 312 Cannon Street. The new building includes a larger gallery and other facilities.

204 Cannon Street