Middlebury, Vermont | Could You Live Here?

A view of Middlebury featuring two of its best-known landmarks, the Otter Creek falls and the stone arches of the c. 1893 Battell Bridge, which was inspired by the Ponte Sant’Angelo.
Credit: Corey Hendrickson

As the season edges toward the holidays, a clapboard hot-chocolate hut—sized for a single person or a cadre of elves—perches curbside in downtown Middlebury. Sidewalks wear a new coat of snow. Strings of lights twine around gas lamps and meander across shop windows stocked with winter essentials: wool blankets, cast-iron cookware, raw honey, the year’s best paperbacks, bottles of aged whiskey distilled less than a mile away. The Otter Creek falls tumble 20 feet beneath the stone Battell Bridge, an architectural nod to Middlebury’s past as a 19th-century hub for marble quarrying.

Meanwhile, in Otter Creek Bakery, Sarah and Ben Wood froth another batch of steaming hot chocolate for the hut with an industrial immersion blender usually meant for soup. For more than 35 years they have co-owned the bakery, which is so cherished by locals that regular orders make up a tome-size collection of index cards tucked beneath the pastry display, a profusion of scratch-made treats anchored by my own go-tos: olive twists, nubbly cornmeal scones, and honey-oat bread emerging warm from the oven each day at 10 a.m. (Reader, this loaf makes the end-all peanut butter and jelly sandwich.)

Middlebury’s small-town ethos happens in tandem with pockets of broader acclaim. Chartered in 1761 and anchored in 1800 by its eponymous liberal arts college, Middlebury is as much an enclave of young families and farmers as it is a destination for academics and winter-sports seekers. I thaw my fingers on a paper cup of cocoa and watch the line grow at the hut: a trio of professors; cheese makers on a delivery run to a local kitchen; a family of four suiting up, toddlers in tow, for a few runs at the nearby Middlebury Snow Bowl. The cocoa is good—really good. Isn’t this just Swiss Miss? “It’s probably the milk,” says the smiling hut tender. It’s from Monument Farms Dairy on Weybridge Street, located a block to my left.

The Setting

Flanked by the Green Mountains to the east and Lake Champlain to the west, Middlebury sits in the valley of Addison County, the largest chunk of agricultural land in the state. The location is as much a boon to hikers, skiers, and sailors as it is to the area food scene, where you’re as likely to find local dairy at the Court Street gas station as you are at the Middlebury Natural Foods Co-op. Perhaps you’ll wander past cows huddled in snowy pastures as you snowshoe along the Middlebury Land Trust’s 18-mile trail system, the TAM (Trail Around Middlebury). Route 7 cleaves Vermont north to south, from Connecticut to Canada, cutting through Middlebury toward the buzzy hub of Burlington 50 minutes away. Enter town where Seymour Street meets Pulp Mill Bridge Road for a route that’s quintessentially New England: through an 1820s covered bridge.