The Keeler Tavern Museum occupies Lott II of the original 1708 Main Street plan of the Proprietors of Ridgefield. By about 1713 Benjamin Hoyt had built the home where he and his wife raised their family. In 1769 Timothy Keeler, Benjamin's grandson, purchased the property from his Uncle David. Timothy and his wife Esther turned the building into T. Keeler's Inn in 1772.
On April 27. 1777, after the Battle of Ridgefield during the Revolutionary War, the Tavern was fired on by British troops proceeding south on Main Street. Timothy, a patriot, was making musket balls in the basement. One British cannonball was imbedded in a corner post where it remains today.
William Keeler inherited from his father in 1815 and ran the now W. Keeler's Hotel with his sister Anna, who inherited the property upon the unmarried William's death in 1827. Timothy Keeler had become 3rd Postmaster of Ridgefield in 1803, and upon his death William took his father's place. After William died neighbor and cousin Thaddeus Keeler became Postmaster with the Post Office remaining in the Keeler Tavern.
Anna Keeler married Abijah Resseguie in 1829 and the hotel name was changed to Resseguie Hotel. Anna Marie, Ann, and Abijah's only child, born in 1830, and her father ran the hotel after Anna's death in 1862 with the help of Phillis Dubois, a free black woman who spent her life as a member of the Resseguie family.
In 1907 Cass Gilbert purchased the property from Anna Marie. It became his family's summer home. Cass Gilbert, architect of the Custom House (NYC), the Woolworth Building (NYC), the Supreme Court Building (Wash.,DC) and many state capitols, and other buildings, made extensive improvements to the Tavern building, and designed the Garden House and Barn.
In 1957, the Gilbert's daughter Emily sold her parents home. Ridgefield residents, concerned about the future of the historic property, formed the Keeler Tavern Preservation Society, Inc., raised funds and purchased in 1965 what in 1966 opened as the Keeler Tavern Museum.