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.
The Federal-style house at 19 Washington Road in Woodbury was built in 1830 by Joseph F. Walker. As related in The Town and People, a Chronological Compilation of Contributed Writings from Present and Past Residents of the Town of Woodbury, Connecticut (1901), edited by Julia Minor Strong:
The honor of longest service as “Chorister” [at the North Congregational Church in Woodbury] probably belongs to Joseph F. Walker (more familiarly known and generally spoken of as “Uncle Fred”). His voice was a peculiarly rich and melodious tenor, always pleasingly prominent in fullest chorus. The very tuning fork that he used for so many years is now sacredly kept by his son, F. A. Walker, of Waterbury, Conn. It always has a place in his vest pocket.
The house later belonged to the Dawson family, who opened a store in 1884 at the corner of Washington Road and Main Street.
As described in the Town of Woodbury History Walk, by Elizabeth Computzzi and William Monti, pp. 60-61, the house at 259 Main Street South in Woodbury was built by Josiah Beers between 1778 and 1784, when it was bought by John Rutgers Marshall (1743-1789), the first Rector of St. Paul’s Church. In 1809 the house was acquired by Judge Charles B. Phelps, husband of Rev. Marshall’s daughter Elsie, from his wife’s older sister and husband. Phelps used the house for both his law office and a tavern. After his death in 1859 the house became dormitory for the neighboring Parker Academy. The roof was raised and dormer windows were added at that time. In the early twentieth century the house was the Woodbury Inn and from the late 1940s until 1980 it was Rest Haven Manor, serving as housing for the elderly. Today it is home to The Elemental Garden, an antiques store.