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.
In the center of Eastford is a Greek Revival building called the Ivy Glenn Memorial. It was built as a Methodist Church in 1847, the same year Eastford separated from Ashford to become a new town. In 1916, Eastford Methodists joined with Congregationalists to form a Federated Church and the former Methodist Church was sold to the town for $200. The building’s basement was repaired to serve as a place for town meetings. Restoration work was completed in 1934 with funds from the Civil Works Administration. The upstairs hall was now used for town meetings and the library and town offices were located in the basement. A new Town Hall was erected in 1969 and after town offices moved to the new building, the library was able to expand in the basement of the former church. This required a new renovation which was funded by a bequest in honor of Ivy Glenn made by her husband, Wilmer Glenn, a New York stockbroker who spent summers in the Phoenixville section of Eastford. The enlarged library opened in 1972. Another renovation was made after a fire in May 1979 damaged the front of the building.
Eastford is one of those towns in the state where the center of population nearly coincides with the geographical center of the township. Miss Ellen Larned, in her valuable History of Windham County, tells us that “the first inhabitant was John Perry from Marlborough, Mass.; who bought 350 acres of land on both sides of Still River and settled upon it near the site of the present Eastford Village.” The grave of this rude forefather of the hamlet may be seen, if I am not mistaken, in the old grave-yard back of the Congregational Church. From the beginning the chief settlement has gathered around this original spot. The village is favorably located, with a healthful environment, a fine outlook, and excellent water power. There are six roads which unite at the village green in front of the Methodist Church; and now that the state road is constructed the facilities for travel are all that can be desired. A fresh hope for the place can be confidently indulged in. The old-time saying of one of its people is fast coming more true than ever before: “Eastford is the biggest place of its size on earth.”
The Congregational Church in Eastford was organized September 23, 1778. A meeting house was soon erected on Lieutenant John Russel’s land. The present church, located at 8 Church Road, was dedicated on December 23, 1829. The old church was removed, as described in Richard M. Bayles’ History of Windham County, Connecticut (1889):
Esquire Bosworth purchased the old meeting house, removed it from the common and made it into a dwelling house. The day for the removal was fixed, men were invited with their teams, and all was ready for the start, when a delegation came to Esquire Bosworth, saying the oxen would not draw unless the teamsters were treated. Esquire Bosworth had recently identified himself with the temperance cause, and the “rummies” hoped to bring him to terms, but they mistook their man. The words of his pastor at his funeral, “He was one of the firmest oaks that ever grew upon Mt. Zion,” were well spoken. Instantly the reply came, “It will rot down where it is, first.” Enough teams were unhitched to prevent the moving that day, but immediately an offer came from neighboring towns to furnish teams that would draw though the teamsters were not treated. Esquire Bosworth left a legacy of a thousand dollars, the interest to be applied to help support a settled orthodox minister, and for the support of no other.
Today the Congregational Church of Eastford is a nondenominational church.
The Sumner-Carpenter House, located at 333 Old Colony Road in Eastford, is a well-preserved example of a large rural Federal period house. It was built c. 1806 for John Newton Sumner (1776-1831), a farmer and land-owner who was active in local civic affairs. In 1815 he was one of the incorporators of the Sprague Manufacturing Company. The builder of the house was Vini Goodell, who also built the Benjamin Bosworth House in Eastford. The year before his death, Sumner sold the house and associated farm to Asa Bosworth. David P. Carpenter purchased the house and farm in 1882 and it remained in his family for three generations, until 1969. The Carpenters maintained a large herd of Devon cattle for their dairy farm. The house has a side ell, built along with or not long after the main block, and a rear wing built c. 1900.
At the corner of Old Colony Road and Westford Road in Eastford (one of the buildings at 245 Old Colony Road near Eastford Green) is a former inn. The earliest part of the building is the rear ell, erected c. 1790-1800. The front section was built c. 1820–1835–1843. The building served as an inn, originally called the Eastford House. For a time, starting in the 1840s, the inn was called the Temperance House. In 1918 the property was acquired by Waldo and Beatrice Kennedy, who renamed it the General Lyon Inn in honor of Gen. Nathaniel Lyon, an Eastford native who was the first Union general killed during the Civil War. He died at the Battle of Wilson’s Creek in Missouri on August 10, 1861. Many of those who attended Gen. Lyon’s funeral in Eastford stayed at the inn. Beatrice E. Kennedy continued to operate the inn and restaurant until 1975. The Inn finally closed in 1979 and is now the Gen. Lyon Apartments.