On September 27, 1966, the Reverend Harry Eid met with eight people at the local Methodist church to discuss the formation of a "senior group" for the Town of Winchester. At their second meeting in October of that year, there were twenty-eight people in attendance. In 1974, the State of Connecticut Department on Aging awarded the Town a grant to operate a senior center and the Winsted Senior Center opened at the St. Andrews Lodge Masonic Home on Wheeler Street. Blanche McCarthy was hired by the Town as the first Director. The Center remained at St. Andrews until 1983, when Mrs. McCarthy secured grant monies to purchase and renovate the Garibaldi Hall on the corner of Holabird Avenue and Chestnut Street.
In 1998, Blanche McCarthy (now Sewell) retired and Ellen Schroeder was named the second Director. In 2016, Ellen retired, and Jennifer Kelley was named the third Winsted Senior Center Director.
Over the years, Winsted Senior Center's mission has evolved to provide educational, recreational, and cultural activities, assistance with medical insurance, health clinics, daily lunches, van transportation, travel opportunities and intergenerational programs.