Old Academy, Fairfield (1804)

Fairfield’s Old Academy was a school founded in 1802 by a group of prominent local citizens. The schoolhouse itself was erected on the Old Post Road in Fairfield and opened in 1804. The original academy was in existence until around 1884. The building then served several purposes over the years, being used by a nearby private school and as a library and place for meetings. In 1920, the Old Academy was faced with demolition but the Eunice Dennie Burr Chapter of the National Society of the Daughters of the American Revolution and the Fairfield Historical Society joined to save and restore the building, which was moved to the town green in 1958. Today the Old Academy is owned by the town and still used by the DAR. Opened to visitors several days a year, the building contains historical artifacts and the second floor is maintained as a replica of the old schoolroom.

The Samuel Seymour House (1784)

The house at 74 South Street in Litchfield is described by Alice T. Bulkeley in Historic Litchfield, 1721-1907 (1907) as follows:

The Seymour house, now St. Michael’s rectory, was built in 1784 by Samuel Seymour, the brother of Major Moses Seymour, who lived there until his death in the early nineteenth century. The south wing was added about twenty or twenty-five years ago. The southeast room on the second floor was used by Calhoun when a law student. Samuel Seymour was a prominent resident of the town and a captain in the militia. He was famous for sharpening razors, and every morning the other members of the Seymour family used to come to his house where they kept their razors, and all shave at the same time. The house was bought in 1860 by Clarissa Seymour, widow of Rev. Truman Marsh, who gave it to St. Michael’s Church for a rectory.

12 Westminster Road, Canterbury (1810)

Dating to around 1810, the house at 12 Westminster Road in Canterbury has a striking Federal-style doorway. The house has been frequently surveyed: in An Architectural Monograph on Old Canterbury on the Quinebaug (White Pine Series of Architectural Monographs, Vol. IX, No. 6, 1923); in the WPA Architectural Survey (c.1935) [Canterbury historic building 028 ]; and in the Historic American Buildings Survey (1940) [the doorway]. The gambrel-roofed ell of the house is believed to be part of an earlier house on the site, the home of Rev. James Cogswell, who ran a school a school for boys there before the Revolution and once had Benedict Arnold as a student.

Sanford-Humphreys House (1793)

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.