Located across from where Pearl Street splits from South Main Street, on a high bluff above the Naugatuck River, is a structure that was perhaps built as early as 1740. It was acquired around 1778 by E. Turel Whittemore and served as a tavern. At that point, the building was only one story high. The second story was added in 1867 by Martin Castle, who dismantled the building’s old chimney and used the stones to constructed the terraced wall in front of the property. On the northwest corner of the old tavern was a barroom, where in 1780 a group of Torries planned the robbery of the home of the Patriot, Capt. Ebenezer Dayton, which was located in Bethany. This infamous incident led to the dramatic kidnapping, in nearby Oxford, of the Patriot boy, Chauncey Judd, a 16-year-old member of the Oxford militia, who ran into the fleeing robbers. They were later captured and sent to Newgate Prison and Judd was freed. The Whittemore Tavern has housed various businesses over the years.
The Sanford-Humphreys House is located at the south-west corner of West and West Church Street in Seymour. It’s oldest section, to the rear, was built in the 1790s by Dr. Samuel Sanford, who became Seymour’s first physician in 1793 and established a smallpox hospital in 1797. After Dr. Sanford’s death, in 1803, the house was enlarged to its present size with the construction of what is today the main block of the structure. It was probably enlarged by General David Humphreys, who at the time was also establishing, with Captain Thomas Vose of Derby, a manufacturing business operating various mills called T. Vose & Company in Humphreysville, as Seymour was then called. In 1810, the company became known as the Humphreysville Manufacturing Company. Judge John Humphreys, the nephew of David Humphreys, later lived in the house. The authors of The History of the Old Town of Derby, Connecticut, 1642-1880 (1880) quote a resident of Seymour who was a contemporary of Humphreys as follows:
Two nephews of Colonel Humphreys represented him in the manufacturing business, and may have had considerable interest therein. The younger, William Humphreys—a fine young man as I first remember him—was the head of the counting-house, and, I think, cashier. The other, John, must have been a lawyer, for he was known as Judge Humphreys, and lived in one of the best houses in the neighborhood, a square white building that stands now on Falls hill, where the road that leads to Bungy crosses the highway. Judge Humphreys and his wife, an elegant, handsome lady, were great favorites with the Colonel, and were generally looked up to in the neighborhood as superior persons. He was one of the finest looking and most dignified men that I remember. Indeed, the whole Humphreys family were remarkable for great personal beauty, both in that and the next generation. Two of Judge John’s daughters, Mrs. Canfield and Mrs. Pease, were beautiful and elegant women.
The first Ecclesiastical Society in what is now Seymour was formed in 1789, when the area was still a part of Derby and known as Chusetown (and later as Humphreysville). The first meeting house was built in 1791 on on Pearl Street, where there is now a Methodist Church. The second meeting house was completed in 1825 where the Old Congregational Cemetery is today. It was known as the Village Church and then the Humphreysville Church. The third and current church was built in 1846-1847 and enlarged, with an addition on the south end, in 1890, when the church was also incorporated as the Seymour Congregational Church. The Albert Swan Memorial parish house was built adjacent to the church in 1907. The church buildings had to be extensively restored after the Flood of 1955.
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.