One of the New Hampshire Grants, Middlebury was chartered by Colonial Governor Benning Wentworth on November 2, 1761.

After the war concluded in 1783, settlers returned to rebuild homes, clear forests and establish farms.

Landowners vied for the lucrative honor of having the village center grow on their properties.

A survey dispute with Salisbury led to the forfeiture of Gamaliel Painter's farm to that town, and his transition from farming to developing Middlebury Village near his and Abisha Washburn's mill, together with other mills that surrounded the Otter Creek falls.

On January 2, 1838, a group of Patriote refugees from the Lower Canada Rebellion met in Middlebury to plan their future course of action.

It was attended by two major Patriote leaders, Louis-Joseph Papineau and Robert Nelson, but they were not able to agree on a unified plan.

Today, as the largest town by population in Addison County, Middlebury serves as the commercial and business center for the region.

Downtown hosts a three-screen movie theater, the post office, and two historic inns, as well as many shops and restaurants.

Foothills of the Green Mountains border the town to the east, with the Champlain Valley to the west.

It is bordered by the towns of New Haven and Bristol to the north, Ripton to the east, Cornwall and Weybridge to the west, and Salisbury to the south.

A new bridge over Otter Creek connecting Cross Street to Bakery Lane opened in November 2010 to serve as a shortcut and alleviate traffic through downtown.

Premier Coach provides an intercity bus line in a joint venture effort with Greyhound via Vermont Translines.