Middlebury, Vermont | Could You Live Here?

A small town that’s big on farmers, artisans, and academics comes gift-wrapped between the Green Mountains and Lake Champlain.

By Yankee Magazine

Oct 24 2019

Winter in Middlebury, Vermont

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 in Rome.

Photo Credit : Corey Hendrickson
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.
Photo 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.

Middlebury College students outside the Axinn Center for Literary and Cultural Studies.
Photo Credit : Corey Hendrickson

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.

Frog Hollow Bikes co-owner Chas Lyons riding at the Rikert Nordic Center in Ripton.
Photo Credit : Corey Hendrickson

Don’t-Miss Attractions

About 20 minutes’ drive from downtown via a mountain pass once meant for cows, Rikert Nordic Center offers cross-country skiing, snowshoeing, and fat biking in a nook of the Green Mountain National Forest. The 35 miles of trails fringe Middlebury’s Bread Loaf campus, a series of cottages painted the soft yellow hue of Christmas lights. It hosts an annual writers’ conference, one of the country’s oldest gatherings of laureates and emerging writers since Robert Frost first helped set up shop in 1926.

Middlebury Snow Bowl, a fully decked-out ski mountain owned by the college since 1934, claims 110 acres of terrain along the nearby Long Trail, the oldest long-distance hiking trail in the country. A tiny lodge offers rentals, lunch, and cocoa and hot local cider for a post-run warm-up. For an in-town family stroll, Middlebury College’s campus is the ideal self-guided walking tour. The windows of Old Chapel are decorated with holiday candles and fronted by an enormous Christmas tree in the courtyard. I poke my head into Starr Library to get a glimpse of what studying looked like when Alexander Twilight, Class of 1823 and the first African American to graduate from a U.S. college, hunkered down here with his studies. 

Eating Out

Sitting on the bank above churning Otter Creek, the Arcadian offers everything from draft negronis to squid ink orecchiette heated with Calabrian chilies to a showstopping bowl of bucatini all’Amatriciana I would happily curl up in. The hardest part of the evening? Choosing which of chef Matt Corrente’s regional house-made pastas to explore first. Come morning, Arcadian co-owner Caroline Corrente turns her attention to Haymaker Bun Co., a sun-drenched spot as beloved for its mugs of locally roasted Brio coffee as it is for its pastry counter: chubby doughnuts, salted chocolate chip cookies, and revelatory sweet and savory brioche buns.

Haymaker Bun Co. owner Caroline Corrente at work on her signature pastry, whose iterations include “the Truffle Pig”(right): bacon, Grafton Farm truffled cheddar, and sautéed leeks.
Photo Credit : Corey Hendrickson

At American Flatbread, the ever-changing roster of Vermont beers has me elbowed up to the bar with a wood-fired pie, which I polish off down to its craggy crust. And for a perfect lunch stop, there’s Costello’s Market, with its homemade mozzarella, fat olives, imported prosciutto, and stuffed-to-order cannoli. Don’t miss the dried pasta selection, either—or the wife-and-husband owners, who are contenders, I think, for “World’s Kindest.”


You would, actually, have to live here to visit the entire cast of artisans, makers, and farmers packed into a town of less than 40 square miles. Alternatively, you can go to the Middlebury Natural Foods Co-op, a bustling grocery stocked with all things local. The Vermont Book Shop offers a range of titles, from cookbooks and literary journals to darlings of the best-seller list. Sweet Cecily has eclectic gifts that encompass locally made jewelry and Vermont-inspired candles and ornaments, while Vermont’s Own Products is the go-to for things like aged cheese and maple syrup (their fudge samples alone are worth the stop). Mendy’s Clothing merges a trendy space with quality fashion brands and plenty of cashmere. Kiss the Cook holds everyday cookware and last-minute holiday splurges, from madeleine pans to a burnt-orange enamel French press.

A Main Street institution for 70 years, the Vermont Book Shop is today run by Becky Dayton (right), who bought it in 2005 from the original owners.
Photo Credit : Corey Hendrickson

Uniquely Middlebury

Stonecutter Spirits cofounder Sas Stewart in the distillery’s aging room.
Photo Credit : Corey Hendrickson

To be in Middlebury—well, to be in Vermont—is to drink like the locals. Tea guru John Wetzel of Stone Leaf Teahouse imports loose-leaf teas from small farms across the globe; the oolong is roasted in-house over coals, while the made-to-order chai comes as spicy as you’d like. Vermont Coffee Company roasts organic beans at its café on Exchange Street, while Stonecutter Spirits offers a bright tasting room and a bourbon barrel–aged gin so nuanced that I relish it straight and slow over ice. Nearby Otter Creek Brewing kegged its first beer in 1991, long before craft beer was Craft Beer. At Drop-In Brewing, brew-master Steve Parkes turns out British-style ales, satisfying hops junkies and dark-mild lovers alike as they listen to the Clash. (Note: Foley Brothers Brewing and Red Clover Ale are off-the-beaten-path gems worth the 20-minute jaunt down Route 7: farmhouse-style brews backed with locally grown inputs at the former, and inventive ales with an eye for classic styles at the latter.)

Where to Stay

Built in 1814, the 20-room Swift House Inn blends farmhouse comfort with old-school elegance. Fires crackle in a sitting room outfitted with plush armchairs and a local fir tree winking with lights. A walnut-hued bar edged with high-backed seats has a quartet of local beers on draft and a nationally lauded wine list. Breakfast is served at the in-house restaurant, Jessica’s, where a spread of coffee, local yogurt, homemade granola, and farm eggs cooked to order are on offer each morning. Homemade cookies beckon from their jar—oatmeal chip one day, peanut butter the next. It’s an easy walk to town, but I find myself spending an afternoon holed up by the fireplace in my room, watching snow fall as the bath fills and wondering where I can buy the sheets.

Christmas in Middlebury, Vermont
A view down Main Street toward the 1809 Congregational Church of Middlebury, topped with a rare five-tiered spire.
Photo Credit : Corey Hendrickson

If You Could Live Here

A lovely valley between lake and mountains, naturally, has its share of million-dollar stunners, like the renovated 1850s farmhouse on 160 acres in Cornwall. Still, there’s ample range in the local housing scene, from a $320,000 four-bedroom colonial with valley views to a $174,000 three-bedroom A-frame with a three-season porch and wood-burning stove.

Editor’s note: This post was updated on 10/28/19 to include the name of the shop Vermont’s Own Products and to distinguish it from another downtown business, Sweet Cecily.