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. Industries would include a cotton factory, sawmill, gristmill, pail factory, paper mill, woolen factory, iron foundry, and marble quarry. The Rutland & Burlington Railroad first arrived on September 1, 1849. Around 1830, Middlebury was the second largest town in Vermont.

Middlebury College, one of the United States’ elite liberal arts colleges, was founded here in 1800. It is a member of the NESCAC. In the summer, the town plays host to the annual Middlebury College Language Schools, as well as the college’s Bread Loaf Writers’ Conference, the oldest surviving conference of its kind in the nation.