Plan a Trip to Vermont’s Southern Green Mountains

A red-painted bridge crosses a stream in Bennington, Vermont.
The historic Paper Mill Covered Bridge in Bennington, Vermont. Photo © Doug Kerr, licensed Creative Commons Attribution Share-alike.

Map of Southern Green Mountains, Vermont
Southern Green Mountains
The easy access to the southern part of Vermont means that license plates from New York and Massachusetts often outnumber the green-and-white plates of the locals. The winding roads of the Green Mountain foothills can get especially crowded on weekends around foliage season (mid-Sept.–mid-Oct.) and during school vacations in ski season. Why go farther north, skiers ask, when mountains like Stratton, Mount Snow, and Okemo offer challenging trails just a couple hours’ drive from Boston?

The three major towns of southern Vermont each have their own distinctive personalities. Brattleboro exudes an artsy, crunchy-granola vibe that wafts from galleries and shops ready-made for browsing. Bennington is a working-class town living off its history as the site of a major battle during the Revolutionary War. Manchester, on the other hand, is anything but struggling. Buoyed by its designer clothing outlets and luxury spas, this is where the New York set comes to get away and play.

In between these relative metropolises are the storybook villages that epitomize New England in the minds of many people. One of the best ways to see this part of the state is just to get in the car and drive. You are sure to come across that perfect gazebo on the town green; a country store packed with homemade fudge and handicrafts; or a maple syrup farm offering tours with the purchase of a jug.

Unlike in the more northerly parts of the state, lodgings and restaurants in this area tend to stay open year-round, making it a nice place to visit in the winter (though be warned that the whole area shuts down during the month of March, otherwise known in these parts as “mud season”). Of course, the region really comes into its own in fall, when the foliage does its annual color dance on the back roads, and country inns often jack up their prices as well. For many shopaholics, a trip to the region begins, stays, and ends in Manchester. Full days of shopping at deeply discounted designer outlets and luxury inns have made the place a destination that can easily fill an enthusiast’s vacation.

Planning Your Time in the Southern Green Mountains

You could easily breeze through southern Vermont in a couple of days, but to really appreciate the area, a leisurely week of cruising the back roads or the ski slopes is more like it. You’re best off basing yourself in Brattleboro, the pint-sized cultural mecca that beguiles tourists. Try to time your trip to take in the monthly Gallery Walk on the first Friday of the month, when the town really displays its artistic talents. While in Brattleboro, you can take a few leisurely days to explore the historic homes of nearby Bellows Falls, the cheese-making operation at Grafton Village Cheese Company, and the quintessentially Vermont Vermont Country Store. Unlike in Brattleboro, there’s not much to see in downbeat Bennington, but it’s worth making a day trip to the city to see the Revolutionary War–era Bennington Battle Monument and accompanying Bennington Museum.

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