Nathan Smith House (1735)

The house at 140 Burrows Hill Road in Hebron was built c. 1735–1744 by a Mr. Porter. It was purchased by the Smith family in 1794 and remained in that family until 2009. Nathan Smith, the second Smith to live in the home, remarried at age 65. In 1853, he added the Greek Revival north ell, where his father lived after retiring from farming. It is one of three additions that have been made to the house’s north side. There is also a kitchen addition at the rear of the house.

The Smith farm grew to hundreds of acres and included Prophet’s Rock, the town’s oldest historic landmark. The legend of Prophet’s Rock is related by Gov. John S. Peters in his “Historical Notes,” written in 1843 and quoted by F.C. Bissell in Hebron, Connecticut Bicentennial (1908). A group of men from Windsor had set out to explore and find places to settle in the area.

While the men were making preparations for their families in the summer of 1706 they brought their provisions with them and remained for weeks at their new home. Their wives being anxious for the welfare of their husbands and unwilling to be left too long alone, four or five started one shining morning for the promised land, twenty long miles through the wilderness, regulating their course by marked trees and crossing the streams on logs felled for that purpose. Night overtook them in the lower part of Gilead, they wandered from the line and brought up on the hill south of Nathan Smith’s house. Fearing the wolves would regale themselves upon their delicious bodies they concluded to roost upon the top of the high rock on the summit of said hill. Here they proclaimed their lamentations to the winds. This novel serenade attracted the attention of their husbands, who wandered towards the sound until they fortunately but unexpectedly found their wives on the rock, which they had chosen for their night’s repose. The gratification of the interview can be better imagined than expressed.

The location of this rock has been handed down to the present time and it is now known as “Prophet’s Rock.”

In 2003, when the Smith family had decided to develop part of their land off Burrows Hill Road, Prophet’s Rock and an easement to reach it from Burrows Hill Road were deeded to the town.

Col. Daniel Brainerd House (1780)

Col. Daniel Brainerd (1752-1809), a farmer, built the house at 275 Saybrook Road in the Higganum section of Haddam about 1780. His sons inherited the house, but it was their sister, Zeruah Brainerd (1786-1877), who lived in it until her death. In the early twentieth century, the house was occupied by Owen Brainerd (1865-1919), an architect who worked with Carrere and Hastings of New York. He designed St. Peter’s Roman Catholic Church (now used as a private residence) on Saybrook Road.

William Ward IV House (1755)

It is likely that the house at 320 Baileyville Road in Middlefield was erected c. 1755. It is thought to have been built for William Ward IV, a farmer (although he was born in 1767). In the 1740s, Ward’s father, William Ward III (also known as William Ward, Jr.), built a nearly identical house nearby, at 137 Powder Hill Road. In 1862, William Ward IV’s heirs sold the house on Baileyville Road to James O. Ross. The house is now part of Country Flower Farms.

Benjamin Hickok Tavern (1760)

The house at 245 Greenwood Avenue in Bethel is believed to have been built in 1760 by Ebenezer Hickok (1692-1774). It was used as a tavern during the Revolutionary War by his son, Capt. Benjamin Hickcok (1750-1816), a veteran of the war who also owned a store and a gristmill. Benjamin’s son, Eli Hickok (1770-1827), later had his hatter’s shop at the address. By 1899, the owner of the house was George B. Fairchild (1857-1931), a partner in the hat manufacturing firm of Farnam & Fairchild.

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James Humphrey House (1790)

The house at 285 Cherry Brook Road in Canton was built by James Humphrey, Sr between 1790 and 1800. The house has two ells that were added later: one in the rear and a large one on the south side that at various times has housed a second family. The Richardson family occupied the house for several generations. Teachers often boarded in the house during the years that the Center District School was located across the meadow road.

Alexander Catlin House (1778)

The Alexander Catlin House, built in 1778, is located at 258 North Street in Litchfield, where the street splits into Goshen Road and Norfolk Road. The colonial home features a gambrel roof and widow’s walk. The house was built by Alexander Catlin, one of the founders of the Litchfield China Trading Company. This may be Alexander Catlin, Sr. (son of John Catlin), who was born in Litchfield in 1738 and died in Burlington, Vermont in 1809. Later owners of the house included Stephen Deming and M. W. and K. L. Buel.