History of the Inn at Woodstock Hill

Plaine Hill
Plaine Hill Road, Woodstock, CT
BUILT: 1816, with additions
OWNERS:Woodstock Inn Association (bldgs, 14 acres)


Plaine Hill is situated prominently at the southern approach to Woodstock Hill. The Inn’s main house, originally constructed in 1816 by John Truesdell for William Bowen, has undergone a number of reconstructions, renovations, and additions over the years. As it appears today, the massive clapboard house has a steeply pitched hip roof, and dormers on all faces. The main entrance is Aerial View of Innmarked by a segmental pediment, which, because of an addition to the north facade, is asymmetrically placed. A large attached barn, which extended to the south of the main house, recently collapsed and was removed, although there are plans to rebuild it in the future. There is also a small dwelling on the property to the south of the main house. Built in 1900 and renovated in 1987, the Cottage has a center chimney, two small dormers on the front, and a shed dormer across the full length of the back. The exterior is finished with wood shingles, and has recently been repainted.


William Bowen, for whom the 1816 house was built, was a descendant of Henry Bowen, one of the thirteen “Goers” who settled Woodstock in 1686, and was the grandfather of Henry C. Bowen who built nearby Roseland Cottage. William Bowen was, in his own right, a selectman of Woodstock, a founder of Woodstock Academy, a tavern keeper (see the Asa Bishop Tavern), and the town’s first postmaster. Following his death, the property passed to his son, Colonel Matthew Bowen, and then to his son, Andrew Williams Bowen, who sold it to his cousin, Henry C. Bowen. The Bowen family connection continued through Henry C. Bowen’s son, Herbert W. Bowen, a diplomat, who retired to Woodstock in the early part of the twentieth century, and Gardner Richardson, Herbert Bowen’s nephew.

The property remained in the Bowen family until after the death of Gardner Richardson’s widow, Dorothea, who bequeathed the farm to the University of Connecticut in 1981 as a memorial to Richardson’s son, Lt. Peter Bowen Richardson, USAF, who was killed in the Korean War. The farm was returned to the family in 1985, and the buildings and adjacent land were subsequently sold to a consortium of investors who converted the main house and barn to use as an inn and restaurant, known as “The Inn at Woodstock Hill.” Most of the farmland remains in the Bowen family as it has for three centuries. Plaine Hill is listed on the National Register of Historic Places.


Bowen, Clarence W., History of Woodstock, 1926.
Lyman, Alexandra, site inspection.
Richardson, Katharine, interview, 1995.
Wood, Elizabeth, A Walking Tour of Woodstock Hill.