Between 1791 and 1801, architect/builder Vini Goodell erected an imposing mansion for Benjamin Bosworth, a wealthy merchant and landowner. Also known as Squire Bosworth’s Castle, this grand Federal-style house is located on John Perry Road in Eastford, near the Congregational Church (Bosworth served on its building committee and removed the previous meeting house from the site). The Benjamin Bosworth House has a distinctive monitor roof. The monitor third floor was built as a Masonic meeting room and retains its built-in benches and has fireplaces at either end. As Janette Trowbridge, a later resident of the house, wrote about the house [included in A Modern History of Windham County, Connecticut, Vol. I (1920), edited by Allen B. Lincoln]:
The framing and sills were laid by the North Star. The hand carvings on the mantels, windows, and doors were elaborate for that time. They were cut with a jack knife by an employee who lived and worked in the house for an entire winter. Squire Bosworth desired a house which should be different from any other in the neighborhood. In this he succeeded, for the house has the appearance of a small gable-roofed house built on top of a larger square-roofed house.