Benjamin Stiles House (1787)

At 1030 Main Street North, across from the “King’s Land” in Southbury, is the stately Georgian-style Benjamin Stiles House, built around 1787. Stiles was the son of Benjamin Stiles, Sr. who, according to the 1892 History of New Haven County, Vol. II,

was probably the first attorney in the town, where he was born in 1720. He graduated from Yale in 1740, studied law and was successful in his profession. His son, Benjamin Stiles, Jr., born in Southbury in 1756, also graduated from Yale at the age of 20 and became a lawyer. He had a large practice until his death in 1817.

The hip-roofed Benjamin Stiles House, occupied by the family until 1920, is said to have been designed by a French engineer in Rochambeau’s army, utilizing the metric system. The building is therefore often referred to as the Benjamin Stiles Metric House. In the early twentieth century, Southbury resident, photographer and antiquarian Wallace Nutting used the house in a number of his photographs.

Mitchell’s Mansion House (1829)

In Connecticut Historical Collections (1836), John Warner Barber features an image of

the Mansion House of M. S. Mitchell, Esq. recently erected, and designed as a house of public entertainment. It is about three quarters of a mile north of the Congregational church. For beauty of situation and superior accommodations, it is not exceeded by any establishment of the kind in any country village in the State. This edifice stands on the spot where the house of the first minister of the place, Mr. Graham, formerly stood.

The Mansion House, on Mansion House Road in Southbury, was built in 1827-1829. One of the builders was James English, later a governor of Connecticut. The house was later owned by the famous furniture-maker Duncan Phyfe, who left the mansion in 1853 to his daughter, Mary, who had married Captain Sidney B. Whitlock, but was a widow by that time. There exists a table, made by Phyfe around 1840, that is known as the “Wedding Cake” table because it held the wedding cake of Phyfe’s grandson, Duncan Phyfe Whitlock, when he married Margaret Donaldson in Southbury.

Oldfield (1818)

Between 1818 and 1822, John Moseley built a house on what is now Main Street North in Southbury. The lumber for the house was said to have been personally selected by Moseley in Maine. After Moseley died in 1876 at the age of one hundred, the house passed through several owners, including Albert and Ruth Aston, who donated the land that became the First Church Green. In 1902, a building across the street, which had once served as an inn or store, was moved and attached to the rear of the house and raised from one to two stories. The house’s interior was also featured in photographs taken by Wallace Nutting during the period when he lived in Southbury. Known as Oldfield, the house has been a bed & breakfast, called Cornucopia at Oldfield, since 1997.

Nuttinghame (1740)

Wallace Nutting (1861 – 1941), a former minister, became a leading antiquarian, entrepreneur and a major figure of the Colonial Revival movement in the early twentieth century. He authored books, reproduced antique American furniture and opened colonial houses as museums, including the Webb House in Wethersfield. He is most well-known for his photographs of country landscapes and the interiors of colonial houses, which were hand colored by women who worked for him and sold through a catalog. In 1906, Nutting had moved to a farm in Southbury, where he soon established a studio in a new barn he built on the property. He restored the old farmhouse, built in the 1740s, and named it “Nuttinghame.” Quite a few Nutting pictures feature Nuttinghame and the landscape that surrounds it. One notable image is titled “Nuttinghame Blossoms.” A particular parlor in the house was featured in many Nutting pictures, including: “A Bit Of Sewing,” “A Sip Of Tea” and “An Afternoon Tea.”

As Nutting‘s business prospered, he decided to move his operation to Framingham, Massachusetts in 1912, where he bought an Italianate house he called “Nuttingholm.” The Framingham house was later demolished, but his earlier house in Southbury still exists. In 1953, the farm was purchased by the comedic pianist Victor Borge. In the mid-1960s, Borge sold the property to a development company, which built a retirement community called Heritage Village. The Nutting/Borge house is now called the Meeting House and has executive offices, meeting rooms and a kitchen for use by community residents.

Bullet Hill School (1789)

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Bullet Hill School is located on Main Street in Southbury. Built in 1789, it is one of New England’s oldest surviving brick schoolhouses. Earlier known as the brick school, it is thought to have acquired its name from a hill in Southbury where bullets were cast during the Revolutionary War (or, in an alternate version of the story, a hill where bullets were discharged during militia practice, which were then remolded for reuse at the school. Used as a school until 1942, the building was saved in the 1960s and and restored in the 1970s by the Friends of Bullet Hill School, which became the Southbury Historical Society in 1974. It is now maintained by the town and the Historical Society and for over twenty years has hosted a living history program for the region’s third graders.