The house at 132 Main Street South in Woodbury sits on a hill just south of School Street. It was built in 1763 by Isaac Tomlinson and was owned early in the nineteenth century by John Boughton, a blacksmith. His blacksmith shop is believed to make up part of the barn on the property. Wallace G. Ward, a builder and president of the Woodbury Savings Bank, later owned and made a number of changes to the house, including replacing the original center chimney and lowering the windows so that his mother could more easily look outside. Since 1916 the house has been owned by the Cassidy family, which undertook restoration work in the mid-twentieth century.
The sign on the house at 55 Good Hill Road in Woodbury displays a date of 1685. That was the year Thomas Drakeley, Sr came to Woodbury. He gave one third of his property to his son, Thomas in 1725 and the house was probably built circa 1725-1730. The Drakeley family owned the house until 1918. The West Side School house once stood across from the Drakeley House. It is said that the school had no water so that the children had to use the Drakeleys’ well.
The house at 60 Main Street South in Woodbury was built in 1829 for Dr. Frederick B. Woodward. The house’s front porch is a later addition. In 1842 it was purchased by Alexander Gordon, Sr. (1814-1893) who owned a tannery across the street. His son, Alexander Gordon, Jr. (1847-1914) befriended the famous wanderer called the Old Leatherman. Gordon provided scraps of leather to replace worn parts of the Leatherman‘s patchwork suit. In 1915 the house was purchased by George H. Benham as a Christmas present for his wife Antoinette Judson Benham.
The building at 357 Main Street South in Woodbury was built sometime in the nineteenth century. Now home to a dental office, it was once the grocery and dry goods store of George N. Proctor, who primarily sold his wares door-to-door. In March 1909, Proctor’s wife disappeared after withdrawing from the bank nearly $1,000 bequeathed to her by a relative. A few hours before her disappearance another resident of town had also vanished: Rev. Charles W. Dane, pastor of the Woodbury Methodist Church. Rev. Dane and Mrs. Proctor’s names had been linked for several months and it was thought they had run off together. Just a week before, Dane’s wife had sued for a divorce, alleging intolerable cruelty. She believed he had been deliberately mistreating her to drive her away so that he could divorce her on the ground of desertion. Mrs. Proctor had arranged to meet the minister in New Britain, but he failed to appear and she went on to New York City alone. Mr. Proctor, who believed the minister had hypnotized his wife to lure her away, soon located her in the city Fifteen years before Proctor had also lost his first wife, who ran off with a clerk from his store.
Next to the North Congregational Church in Woodbury is the church parsonage. It was built circa 1828-1829 as a residence by Leman Sherman, who died in 1831. It passed through other owners until 1871, when it became the parsonage and has been a home to the ministers of North Church ever since. The parsonage, which was in danger of collapsing, was extensively restored and the interior modernized in 2012-2013.
Early Catholics in Woodbury were few in number and were subject to various ecclesiastical jurisdictions in the nineteenth century. While under the jurisdiction of Watertown, the cornerstone of a mission church was blessed on June 30, 1903, and the dedication was held on September 4, 1904. St. Teresa of Avila Church in Woodbury and St. John of the Cross Church in Middlebury were established together as a parish on March 1, 1916. The parochial seat was moved to Middlebury in 1922, but in 1955 St. Tereasa of Avila became an independent parish.