[4] The village of Middlebury grew as one of Addison County's early industrial centers, due to the presence of a significant waterfall on Otter Creek.

The local Congregational Church, built 1806–09, is the oldest in the county, and is a fine example of Federal period architecture.

Also impressive are the Middlebury Inn, built 1826 and restyled later in the 19th and early 20th centuries.

Middlebury College was founded in 1800, and its campus is located just southwest of the village center.

Another important educational milestone was the 1814 founding by Emma Willard of a private school for women, located in her house on South Main Street.

[5] Much of the village was listed on the National Register of Historic Places in 1976, with a significant enlargement in 1980.