A Weekend in Southern Vermont
Green mountains, arts and history
Day 1: The Shires Region
Vermont’s southwestern region is home to two shire towns, historically referred to as county seats. Bennington and Manchester are the largest towns in Vermont’s Shires region, and between them lies a stronghold of Vermont’s history and culture.
Bennington makes for a strong start to a day in the Shires. Vermont is steeped in writerly history, found at the Robert Frost Stone House Museum at Bennington College. From there, head to the center of town to Bennington’s historic district, where travelers will find Old First Church, first gathered in 1762, and the Bennington Battle Monument, the tallest structure in Vermont commemorating a pivotal victory for American forces on the New England front of the American revolution. Four hundred and seventeen steps lead visitors to the top of the monument, where views of the Green Mountains await. Also in Bennington is the Bennington Museum, curating exhibits on Vermont’s past and present through art, history and the landscape itself.
Nearby is Bromley Mountain Resort, offering four-season fun including mountain biking, hiking, mini golf, a waterslide and in the winter months, skiing and riding.
Wind your way through the Shires region by way of Shaftsbury, home to a section of Green Mountain National Forest, offering waterfall views and trails for a wide range of ability levels. Lake Shaftsbury State Park is also along the way.
Mount Equinox, one of Vermont’s highest peaks, is accessible either by trail or by car on the Mount Equinox Skyline Drive.
Day 2: Southeastern Vermont
Heading toward Dummerston from Brattleboro, travelers can find Naulakha, the historic home of writer Rudyard Kipling, meticulously restored for lodging.
GET THE MAP
As you navigate your way around this itinerary, use this map to pinpoint destinations and get directions. Where you go from here is up to you!