WINY first signed on the air on May 3, 1953 under the call letters WPCT. The station was financed by three French Canadian businessmen from Central Falls, Rhode Island: named Goyette, Albert Lanthier, and Rene Cote. The station was managed by Daniel Hyland with an original announcing staff of Dick Alarie, Ed Read, and Frank Carroll.

The call letters were changed to WINY in September 1960 when the station was purchased by the Herbert C. Rice family and the Winny Broadcasting Company. The call letters were changed to represent the station's new mascot, "Winny, The Community Gal," who was a counterpart to the mascot at sister station WILI, "Willie, The Community Man." The family combined the operations of the two stations into Nutmeg Broadcasting Company, which would go on to own a total of five radio stations throughout Connecticut, including WNTY Southington, WLIS Old Saybrook and WILI-FM Willimantic.

WINY changed hands in 1990 to the Gerardi Broadcasting Corporation, and once more in 2001 to the current owners, the Osbrey Broadcasting Company.

WINY produces its own programming between 06:00-18:00. Programming from 18:00-6:00 is provided by Dial Global.