Woodward House (1740)

On the northwest corner of Bethlehem Green is a saltbox house built in 1740 by Samuel Church. In 1797, his daughter Betsy Church married David Bird and the house became known as the Bird Tavern. According to The History of the Descendants of Elder John Strong, of Northampton, Mass. (1871), by Benjamin W. Dwight, their son, Joshua Bird, was “for 30 years a woolen manufacturer at Bethlehem (1820-50), and for 20 years past (1850-70) a farmer there, a deacon in Ihe Cong. Ch. for 25 years (1845-70), a state senator (in 1859).” He also helped fugitive slaves and his house was a stop on the Underground Railroad. The house also served as the town’s post office. James W. Flynn, who purchased the house around 1900, served as postmaster and town clerk in the early twentieth century. Flynn and his wife Mary later shared the house with their foster child, Mary E. Toman. She married Charles Woodward, the son of a local farmer, and the couple inherited the house. It later passed to other owners, but in recent years was restored to become a restaurant called the Woodward House.

Gen. Gold Selleck Silliman House (1756)

Known as “The Orchard,” the Gen. Gold Selleck Silliman House is located at 506 Jennings Road in Fairfield. A general in the Revolutionary War, Silliman took part in the Battle of Ridgefield in 1777. In May 1779, Silliman and his son were captured in their home by a party of tories who had crossed Long Island Sound in the night. U.S. Navy Captain David Hawley later captured Thomas Jones, a highly reputed loyalist, to exchange for Silliman a year after his capture. Gen. Silliman‘s house was also used as a place of refuge by citizens fleeing the British burning of Fairfield on July 8, 1779. Gen. Silliman’s son, Benjamin Silliman, became the first professor of science at Yale University and the first to distill petroleum.

Old Gungywamp (1670)

Gungywamp is an archaeological site in Groton, known for its stone chambers and double circle of stones. The builders of these structures and their function has yet to be definitively established. Old Gungywamp is a colonial saltbox house. It was built around 1670 near the Thames River in Groton, not far from the Gungywamp complex. It is also known as the Wood-Allyn House. In the 1920s, it was acquired by Elmer D. Keith, an antiquarian who was later the director of the WPA Federal Writer’s Project Census of Old Buildings in Connecticut and author of Some Notes on Early Connecticut Architecture (1938). In 1945, he moved Old Gungywamp from Groton to its current location at 892 Clintonville Road in Wallingford.

Bryan-Downs House (1785)

The first residents of the Bryan-Downs House, originally located on the Post Road between Milford and New Haven, were Jehiel Bryan, Jr. wed Mary Treat, who were married in April, 1784. It was then the home of their daughter, Mary Esther, and her husband, Ebenezer Downs. Their son, Ebenezer Jr., inherited in 1837 and made a number of major changes to the house, replacing the original stone chimney with a smaller one and remodeling the interior. After Ebenezer’s death in 1873, the family rented out the house, which was later dismantled and stored for several years. In 1977, it was erected on the Milford Historical Society property, where today it forms part of the Wharf Lane complex of historic houses.

Loomis Homestead (1640)

The oldest house in Windsor is the Loomis Homestead, located on the campus of Loomis Chaffee school. The oldest part of the house is now the south ell, built by Joseph Loomis in 1640. His son, Deacon John Loomis built the main section in 1688, the year he died, possibly for his son Timothy. In the 1870s, planning began for what would become Loomis Chaffee, established by five Loomis siblings, children of Colonel James Loomis and Abigail Sherwood Chaffee, who had all lost their own children. The school’s first buildings, completed in 1913-1916, were designed to match the axis of the Loomis Homestead, several degrees off of true north. The old house itself remained in the Loomis family until Miss Jennie Loomis deeded it to the Loomis Institute in 1901. She continued to reside in the house until her death, in 1944. Then it became a residence for a member of the Loomis Chaffee School faculty and continues as a museum and memorial to the Loomis family.