Seymour’s old two-and-a-half story High School, with its imposing bell tower, was built in 1884 to 1886. At one time considered one of the most efficient and well-equipped high schools of its kind, the institution grew over the years and an annex building was constructed next door. Finally outgrowing the available space, a new high school was built in 1916 and the old buildings, known as the Center School and Annex, became an elementary school until 1977. After briefly housing the Seymour Historical Society museum in three of its classrooms, the old high school building has since been converted into offices for private businesses. The Annex building now contains the Seymour Board of Education, Senior Center, and a nursery school and teen center.
In February 1797, a new Episcopal church was organized at a meeting in the home of Dr. Samuel Sanford in Seymour. By spring, the cornerstone for a church building had been laid but, due to a lack of funds, Union Church was only completed in 1816. Rev. Richard Mansfield served as the part-time rector until 1802. The church grew over the years and, in 1853, its name was changed to Trinity Episcopal. In 1857, the church was almost completely rebuilt, starting with only the old framework of the building, under the direction of architect Henry Austin of New Haven. There have been changes to the church over the years. The current spire is not as tall or complex than the one Austin originally built. At one time, the church also had Victorian-style ornamentation inside, but in 1997, when the church celebrated its 200th anniversary, the interior was completely renovated in the Colonial Revival manner.
Dr. Joshua Kendall came to the Humphreysville section of Derby (now the town of Seymour) from Pennsylvania in 1833 and practiced medicine in town for over fifty years. According to The History of the Old town of Derby (1880), by Samuel Orcutt and Ambrose Beardsley, Dr. Kendall,
attended medical lectures at Castleton University, Vt, where he graduated. As a physician and as a citizen he has been a leading and influential man; has been a most efficient member of the school board over thirty years, and has done good work for the advancement of education, temperance and sound morality in the town. He has been ardent and unyielding in his politics and represented Derby in the Legislature in 1849, before Seymour was organized as a new town.
The home of Dr. Sheldon C. Johnson of Seymour is located at the intersection of West and Church Streets. This intersection could be called “Doctors Corner,” because doctors lived in each home at the four corners. Dr. Johnson settled in Seymour (then called Humphreysville) in 1825. He married Hannah Stoddard, the daughter of Dr. Abiram Stoddard, and the couple at first lived in an eighteenth century house, located behind the home Dr. Johnson later built in 1842. Dr. Johnson continued practicing medicine in the area into his 80s. The couple’s son, Charles Napoleon Johnson, became a lawyer.
The Stiles-Stoddard House in Seymour was built on the site of an earlier home, constructed by the son of a Pequot sachem, named Joseph Mauwehu, who was also known as “Chuse.” Joseph and his followers lived in an area of land known as Indian Hill, which was north of the Naugatuck River near the Great Falls. From around 1740, the Indians lived peacefully with the white settlers who were moving into the area, but eventually the newcomers numbers grew to an extent that made it difficult for the Indians to follow their traditional way of life. After living more than four decades in the area, Joseph then left with his tribesmen and moved to Kent, where their was a larger Indian reservation. Seymour was first known as Chusetown, named in honor of Chief Joseph. In 1795, Nathan Stiles built his house on the site where Joseph had lived, at a fork in the road, where today Pearl Street splits off from South Main Street. After Stiles’ death in 1804, his widow, Phebe Dayton Stiles, lived in the house and owned land on Indian Hill. Over the years, many people sought to buy her land, and to each of them she promised to sell it eventually, but these promises were so often repeated without her selling to anyone, that Indian Hill came to be known as the “Promised Land.” The house was later received by Dr. Thomas Stoddard as a gift from his father. In 1898, when C.H. Lounsbury owned the house, he raised and repaired the building, converting it into a two-family home.