An extraordinary early 19th century building boom and a 20th century road improvement project created Chaplin, a village suspended in time. In the late 1700s, residents of what is now Chaplin had no town of their own. Their lands were divided among Mansfield, Hampton and Windham. To attend church, they had to travel a considerable distance over bad roads, often in inclement weather. Benjamin Chaplin, a wealthy deacon of the Mansfield church, who built his home on the Natchaug River, was among those who regularly made this long and uncomfortable trip to attend his duties. Before Chaplin died in 1795, he bequeathed three hundred pounds ($1,500) to form an ecclesiastical society charged with building a new meeting house on the condition that this church be built within a mile and a quarter of his homestead.

The Chaplin church was built between 1812 and 1815 on Chaplin Hill, a knoll along the highway a half mile from Chaplin’s home. Then between 1820 and 1850, approximately 25 homes, a tavern, a general store, a dry goods store and a merchant’s store were built adjacent to the church along a curved portion of the major north-south route that paralled the Natchaug River. As a consequence, the majority of the houses that line the Chaplin Village street were built within a single thirty-year period. In 1822, the residents of this new village negotiated with the towns of Mansfield, Hampton and Windham to incorporate Chaplin, named in honor of the town’s benefactor. Chaplin Street, as it is now called, became a mile long cut-off when State Route 198 was straightened in 1929, thus leaving most of the village homes intact and creating a unique study in time in northeastern Connecticut. In July 1974, Chaplin Village was designated a Historic District to preserve the character of the buildings and their settings for future generations.