Competing theories exist about how the college town of Middlebury got its name. Some theorize that it was named for its location halfway between the Massachusetts and Canadian borders; others surmise it was named as the midpoint between two neighboring towns that were settled the same day in 1761. Whatever the origin, Middlebury has grown over the years into the cultural hub of the Champlain Valley, in large part to its eponymous liberal arts school, Middlebury College.

The college was founded in 1800 by Gamaliel Painter, one of the town’s first settlers and a profoundly religious man who wanted to safeguard the spiritual education of local farmers’ sons against the savage secularism of the nascent University of Vermont in Burlington.

Buoyed by the college and a variety of industries including grist and woolen mills and marble quarrying, Middlebury became the largest community west of the Green Mountains by the mid-19th century, surpassing Bennington, Manchester, Rutland, and even Burlington. Since then, its population has leveled off at a modest 8,000 souls, who enjoy an energetic downtown full of upscale shops and restaurants.

In town are several high-quality museums associated with the college; many students come here equally for the college’s enviable access to the outdoors in the form of the Green Mountain National Forest, just a few miles east.