Capt. Samuel Comstock House (1808)

In 1805, Capt. Samuel Comstock II was given land in West Centerbrook (now Ivoryton) by his father. Circa 1808, Capt. Comstock built the house at 123 Main Street (although it may also be an earlier residence, c. 1795, on the site that he enlarged at that time). A sea captain in the West Indies trade, Comstock was the father of Samuel Merritt Comstock, who established his ivory factory across the street in 1847. In 1857, the house was acquired by Marsena Comstock, who started his own ivory business on the property.

Gurley Tavern (1822)

The old Gurley Tavern at 42 Chaplin Street in Chaplin is an impressively detailed Federal-style residence. It was built c. 1822, the year the Town of Chaplin was incorporated, as a stagecoach inn. An upstairs ballroom, which later housed a private school, has since been converted to a bedroom and bathroom. An addition connects the building to a barn at the rear. During the twentieth century, for fifty years the former tavern was the residence of quilt maker Ruth Snow Bowen and was known as The Quilt Shop. The Chaplin Post Office was located in the north parlor from 1950 to 1965. The building, later in rough condition, underwent a major restoration in 1999-2000. It began taking guests as the Old Gurley Tavern Country Inn, but was later subject to a foreclosure.