The Matthew Bowen Homestead / The Inn at Woodstock Hill

The house now known as the Inn at Woodstock Hill was constructed in 1816 by William Bowen and later became known as the Matthew Bowen Homestead. Located on Plaine Hill Road, it was part of a working farm owned by generations of the Bowen family, one of Woodstock’s most prominent early families.

The original house was a five-bay Federal-style farmhouse. As the needs and tastes of its residents changed, the property was enlarged and updated. During the 1880s, Henry Chandler Bowen, owner of nearby Roseland Cottage, oversaw an extensive expansion that included Victorian porches and a turret. Many of these additions were removed during a major renovation in 1929, when the house was expanded to six bays and given much of its present Federal Revival appearance.

The property developed into a substantial farm complex that included barns, a carriage house, and other agricultural buildings. It remained within the Bowen family and continued to be used as farmland until 1982, preserving a connection to nearly two centuries of agricultural life in Woodstock.

The homestead was added to the National Register of Historic Places in 1987 as a well-preserved example of a Federal-period farmstead. Its later conversion into the Inn at Woodstock Hill gave the historic house a new purpose while retaining its traditional character. What began as a family farmhouse now welcomes visitors to the same rural landscape that generations of the Bowen family once called home.