About the Windham County Jail Building
When the Shire Town of Newfane moved from atop of Newfane Hill to its current location in the Village, the County Jail building and the County Courthouse were the first two structures erected on the Common in 1825. The County Jail building defines the East side of the Common and faces the County Court House across Main Street to the West.
The north side of the Jail building served as a secure jail right up until 1971. All original features were carefully restored during the extensive restoration of the building's interior in 2024 for the adaptive use of the building as the Historical Society's main County History Museum. The windows on the three floors of this section are still secured by iron bars. The six individual jail cells on the first floor and the women's jail quarters on the third floor are separated and secured by iron bars and iron doors from the rest of the building, which was used as the Sheriff’s living quarters and office space.
For over 150 years, a hotel wing (The County House) adjoined the jail building. The hotel accommodated visiting jurors and judges as (well as tourists) at a time when commutes to Newfane and the Courthouse required at least an overnight stay. The West River Railroad was a convenient mode of travel to Newfane at the time. The hotel’s cuisine rivaled many other establishments in the area, and was served to hotel guests as well as the “jailbirds.” After visiting the area, Theodore Roosevelt said he “would like to retire here, commit some ‘mild crime’ and eat his way through a cheerful old age.”
Windham County Jail Timeline
1825 - The site of the Shire Town of Newfane moves from atop of Newfane Hill to its current location in the valley. The County Courthouse and County Jail are the first public buildings erected in the Village.
1854 - The first improvements are made when both public buildings are renovated. The ell portion of the jail building is brought out square with the front and made a part of the main building. The front receives a two-story verandah surmounted by a large gable, which spans the entire facade. Inside, the barred walls for prisoners are built. The brick exterior is painted.
1895 - The hotel wing is built to accommodate County judges, lawyers, jurors, and the public. The Jail’s barn is detached and moved south to make way for the addition of the hotel. The Jail building’s width is almost tripled.
1914 - Sixty years after the first improvements in 1854, a second ‘modernization’ takes place when the Jail is made into a sanitary and fireproof institution. Each cell is provided with private lavatory, running water and electric lights.
1934 - Sheriff O’Keefe turns over his Jailer duties to Mabel and Charles Whitney so he can live in Brattleboro. The Whitneys run the Jail and the attached Hotel for the next 22 years.
1956 - Due to the declining occupancy in the Hotel (in large part a result of improved transportation to the area by automobile), the Windham County Hotel (or the County House as it was also called) is razed. The portion of the brick jail which contained five of the hotel’s 15 rooms, is made into living quarters for Sheriff Robinson and his family, with kitchen, living quarters, office, and reception room.
1971 - The Jail is closed under new legislation for an integrated state correctional system.
1974 - The Court reaffirms the protection of the historic Common in Newfane, the County Courthouse and Jail buildings.
1986 - The Jail building’s interior is modernized to serve the Windham County Sheriff’s Department.
2022 - The Windham County Sheriff’s Department moves to Brattleboro. The Historical Society of Windham County expands the History Museum into the County Jail Building.
*Excerpted from Robert Crowell’s Historic Newfane Village.