The Middlebury Green is a horseshoe-shaped open space in the center of town at the juncture of Route 188 and North and South Streets. It is simply landscaped with randomly planted mature, healthy maple trees that provide a green canopy over the lawn. Near the center and toward the eastern end is a small evergreen tree. There are no monuments or paths. The only man-made object is a cast iron sign post at the southwest corner indicating the distance to nearby towns. The most dramatic element of the green is the view to the south where the valley and the hills beyond are evident.

Located within the Middlebury Center Historic District, it is the focal point of the small community. It is the center of religious and civic activity, as well as being bordered by the Westover School (1906-1909) and residences built primarily during the first half of the 19th century. West of the green and the most prominent feature of the streetscape is the Congregational Church. It was built in 1935, but as a replica of the previous church built in the Greek Revival style in 1840, thus helping to retain the 19th century character of the town center. To the west of the church is the Town Hall, a red brick structure in Federal Revival style constructed in 1936 and sympathetic to the historic character of the center.

Dramatically sited across from the southwest corner of the green and diagonally facing it is the Catholic Church (1902-1907), a structure built of fieldstone. Also facing the green is the Methodist Church (1832) now used as a library by the Westover School. The school next to the church on the south side of the green replaced a store and blacksmith shop on the site when it was constructed in 1902-1907. The long stuccoed elevation (270') is a major presence on the green.