St. John of the Cross Parish in Middlebury began as a mission church of St. John the Evangelist Parish in Watertown and achieved parish status in 1916. The cornerstone of its stone church on Middlebury Green was blessed on October 4, 1907 and the church was dedicated on November 22, 1914.
In 1935, a fire destroyed the Congregational Church and neighboring Town Hall (built in 1896 and remodeled in 1916) in Middlebury. They were rebuilt the following year, both to designs by the architect Elbert G. Richmond (1886-1965)
The Congregational Church in Middlebury dates back to 1791 and the first meetinghouse was built in 1794 on the town Green. The steps, built of stone quarried in Roxbury, and the church bell, cast in Troy, New York, were reused in the second meetinghouse, built in 1839. On April 8, 1935, the church and the neighboring town hall were destroyed in a fire. The bell was shattered but the pieces were recast to make a new bell. A new church was built in 1935-1936 as a replica of the destroyed second meetinghouse. Additions were made to expand the church in later years.
The Westover School is an independent preparatory day and boarding school for girls in Middlebury. Plans for the school’s quadrangle were completed in 1907 by Theodate Pope for Mary Hillard, Westover‘s first headmistress, who had sought to establish a school west and over the hill from Waterbury. The building was completed and opened in 1909. Designed in the Colonial Revival style, to harmonize with other structures around Middlebury Green, the Westover School building features a hexagonal cupola above the central entrance pavilion, with a Gothic chapel projecting on the east end of the structure and the cottage-like quarters of the headmistress on the west. In 1916, Theodate added Virginia House, an art and music studio, to the Westover campus.
In 1911, Theodate Pope Riddle, famous for designing Hill-Stead in Farmington, completed plans for another country estate for her friends, Joseph and and Elizabeth Chamberlain. In 1909, the Chamberlins had acquired land in Middlebury, close to Whittemore estate. Their house, called “Highfield,” was constructed in 1911-1914, on a hill above Lake Quassapaug. Theodate’s design for the house was influenced by her recent trip to England, where she had studied traditional village architecture and the work of English Arts and Crafts architects like Edwin Lutyens. Designed to resemble a rustic English cottage, Highfield has a large interior, with the second story cleverly concealed behind the sloping shingled roof. Next to the house is a sunken garden, where Theodate created a sumer house with removable glass walls. Charles Downing Lay made alterations to the back of the house in 1925 and to the attic in 1929. In 1954, the Stillman family, who had suceeded the Chamberlins as owners of the house, sold the property, which became a nine hole golf course. The house is now the clubhouse.
The oldest surviving house in Middlebury was built by Josiah Bronson on Breakneck Hill Road in 1738. The house also served as a tavern and hosted a number of French officers during the Revolutionary War: first in 1781 when Rochambeau’s French army encamped in Middlebury from June 27 to July 1, on its way to the Siege of Yorktown, and again from October 26-28, 1782, during their return journey. One of the officers to stay in the tavern was the Baron de Viomenil, who was second in command to General Rochambeau during the Yorktown Campaign. At these times, Rochambeau himself most likely stayed with Captain Isaac Bronson, Josiah’s father, further down the hill. The Josiah Bronson House was acquired in 1940 by Lawrence M. and Esther Duryee, who restored it.