The Best Trails, Ski Slopes, And A Cozy Downtown Are Found In This New England College Town

If you had to put one Vermont town on the cover of a calendar, it should probably be Middlebury. Of course, the state has other college towns, ski towns, and towns with farm-to-table dining and cozy inns. You could probably find other stone bridges spanning scenic waterfalls and marble factories converted into specialty shops. Plenty of Vermont shire towns have their central greens, pastoral gazebos, historic brick buildings, and congregational churches. But Middlebury has all of these things — and so much more. If you want to know what the Green Mountain State is all about, Middlebury is a shining beacon of Vermont culture.

The community of 9,000 residents has an outsized reputation, partly because of Middlebury College, a prestigious liberal arts school known for both academics and athletics. But there's also the natural setting: Photographers already love to road trip through this slice of New England, and the Champlain Valley is nestled between the Green Mountains and the Adirondacks, so the horizon is always rich with mountain views. Otter Creek is one of those rare bodies of water that flows in a northerly direction, snaking through forest and farmland. In Middlebury, Otter Creek descends into dramatic falls, which pool beneath a stately steel foot bridge. Middlebury is beautiful in all seasons, from sunny summer to blazing fall and snowy winter, and the surrounding villages of Addison County are packed with outdoor activities.

Middlebury was first chartered in 1761, in the days of wagons and draft horses, and its center remains extremely walkable. Main Street is lined with vintage facades that date back to the 19th century, and the town's centerpiece is St. Stephen's Episcopal Church, a gothic stone beauty. Take a walk down Main Street and you'll find yourself on the college campus, where impressive old complexes — many composed of stone — mingle with grassy lawns, gentle slopes, and the world-class Mahaney Arts Center. Other high points along the way are the Vermont Book Shop, the Town Hall Theater, and the beloved Frog Hollow Craft Gallery, among countless other iconic nooks.

But avid hikers can also walk the circumference of town, thanks to the unique Trail Around Middlebury (TAM). This 18-mile loop traces the outskirts of Middlebury, through woods and meadows, across bridges, around a golf course, and to the top of Chipman Hill, the town's highest point. Most people take segments of this trail on foot, but you're welcome to attempt the whole thing. Select portions permit mountain bikes as well.

Meanwhile, Otter Creek is popular with paddlers, and Middlebury is only a 20-minute drive from the southern portion of Lake Champlain, a must-visit East Coast destination for history buffs. The landscape of rolling hills and traditional dairy farms has won over countless visitors — and long inspired renowned Vermont artist Woody Jackson. Whether you're exploring by land or water, Addison County is a New England arcadia.

Middlebury is active year-round, but winter is one of its busiest seasons. The Middlebury Snowbowl draws downhill skiers and snowboarders from across the state. While the Snowbowl isn't a famous resort like Killington or Stowe, the mountain boasts 28 trails across 110 acres — including three chairlifts and 1,020 feet of vertical drop. Equipment can be rented on-site, and patrons can expect good coverage most of the winter; the mountain receives an average of 200 inches of snowfall per year, and six Snowbowl trails are equipped with snowmaking machines.

If you're looking for a real workout, though, you might consider cross-country skiing, another popular Middlebury pastime. The best-known destination is the Rikert Outdoor Center, located in the nearby mountain town of Ripton and owned by Middlebury College. After arriving at the historic yellow houses, you can throw on your skis and trek across 34 miles the backcountry trails. Snowshoes and fat-tire bikes are also welcome.

Most visitors to Middlebury will drive there in their own cars. But the nearest airport is Patrick Leahy Burlington International, about an hour north. For train lovers, there's another option, as well: an Amtrak station recently opened in downtown Middlebury, as part of the Ethan Allen Express from New York City to Burlington. This gorgeous route is a nice alternative and eliminates the need to drive at all. (The nearby Vermonter line is also considered one of the most beautiful winter train rides in the country.) A night at the Middlebury Inn or Swift House will run between $100 and $200; the Courtyard Middlebury chain will cost a little over $100. And there's no better way to celebrate your arrival than a brew at Two Brothers Tavern, Middlebury's principal pub.