Born in Westford, MA, Captain Proctor was a Revolutionary soldier and served as the company’s Second Lieutenant on the Lexington Alarm of April 17,1775. He was part of a brave group of “minute-men” that fought in the opening battle of the American Revolution. Forty-one years old at the time and father of seven children, Proctor eventually served under General Washington.
Moving to Cavendish Vermont in 1783, Proctor built a log cabin in the western part of the township and brought his family to their new homestead in the winter of 1784. Next to the homestead, he constructed a home and tavern, near where the Methodist Church now stands. The house stood where the present highway runs. Part of the house was moved, and then torn down to make way for the elementary school. The remaining part of the house was moved to the current location and became known as the Page House. In 1787, he built what is known today as the “Jenny House,” where he and his wife Mary Proctor lived for over 30 years. The house, built of wood, is famous for its fancy hand-carved decorations around the roofline, on the corner posts and around the center doorway.
Proctor and Salmon Dutton, the latter who had come to Cavendish in 1781, had much in common. They served in the Westford militia and were friends for many years. In 1784, Dutton was appointed surveyor for the toll road that was to be built between Cavendish and Ludlow to the west. The planned turnpike would become the only road connecting Duttonsville and Proctorsville. This toll road in 1798 became part of the Green Mountain turnpike that connected Bellows Falls and Rutland. The route from Cavendish south went over Dutton Hill to Gassetts and Chester, VT.
A break between the two families arose over the road and its operation. The Proctors were determined not to pay tolls to Dutton for the use of the Cavendish section of the road. The Proctor men built a “shun-pike,” which passed directly south from Proctorsville to Gassetts. This shunpike became the present highway for the Sate of Vermont. Because of the road, the Dutton and Proctor families, as well as the villages of Duttonsville and Proctorsville, feuded for 75 years.
The marriage of Redfield Proctor and Emily Dutton in 1858 joined the leading families of the two villages and promised to put an end to the former rivalry. As Redfield said of his first son, Fletcher Dutton Proctor, "if the old names and blood had the old inclination left to stir up strife, it would have created a fearful internal commotion." In fact, the merger of these families proved to be a propitious event for Vermont, since three governors and a United States Senator came from this Dutton-Proctor line.
In February 20, 1907, Proctorsville formally gave notice to the Town of Cavendish that it wished to be incorporated. Today Proctorsville is a village within the township of Cavendish.
Leonard Proctor and other family are buried in the Proctor Cemetery, just off Main Street in Proctorsville.
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