The town was only a short train ride from New York City, yet retained a rural character that appealed to artists.
Many of Twachtman's friends came to visit him at his home; among them were Hassam, J. Alden Weir, Theodore Robinson, Henry Fitch Taylor, and Robert Reid.
During the winter, Twachtman and Weir taught at the Art Students League of New York.
Probably beginning in 1890, Twachtman established summer art classes in Cos Cob; Weir taught with him in 1892 and 1893.
Among the artists who first visited Cos Cob as summer students were Elmer Livingston MacRae, Ernest Lawson, Allen Tucker, Charles Ebert, Mary Roberts Ebert, Alice Judson, and Genjiro Yeto.