Southern Vermont Itinerary

A Weekend in Southern Vermont


Vermont’s southern region offers travelers views of the Green Mountains, including sections of the Taconic Range, and a banquet of Vermont arts, culture and history.

Southern Vermont is home to the Battenkill River, where travelers can paddle, raft or float at their own pace, as well as Mount Equinox, the Taconic Range’s highest peak. Outlet shopping abounds in Manchester, also home to the best date-night restaurant in America, according to TripAdvisor. In Bennington and Brattleboro, explore Vermont history and uncover the stories of Vermont’s beginnings.

However you explore, this itinerary for a weekend in southern Vermont will inspire your trip planning and help you get the most out of your time in Vermont’s southernmost region.

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.

Before reaching Manchester, pass through Arlington, former home of famed artist Norman Rockwell, whose depictions of New England life graced the cover of the Saturday Evening Post for decades. The Rockwell Retreat, newly restored, is available for lodging. While in Arlington, don’t miss the Chocolatorium.

Manchester, the region’s other shire town, is home to the American Museum of Fly Fishing and the Southern Vermont Arts Center. Explore high-end goods at Manchester Designer Outlets.

Mount Equinox, one of Vermont’s highest peaks, is accessible either by trail or by car on the Mount Equinox Skyline Drive.

Get to know the Lincoln family at Hildene, the Lincoln Family Home, the family’s summer lodge. Visitors can take tours, explore the expansive grounds and see artifacts from President Lincoln’s life, including an original Pullman train car.

Day 2: Southeastern Vermont

Heading toward the eastern side of the state, visitors will find historic downtown Wilmington, near Mount Snow Ski Resort, offering golf, mountain biking, hiking and, of course, skiing and snowboarding.

Further find Brattleboro which features a historic downtown, but also the rural setting of Retreat Farm, where all ages and ability levels can explore the farm and learn about farm animals and agriculture on 500 acres of conserved land. Brattleboro Museum and Art Center offers a window into Vermont’s past and its artists’ inspiring work. Explore the history of the Vermont-made Estey Organ at the Estey Organ Museum.

Heading toward Dummerston from Brattleboro, travelers can find Naulakha, the historic home of writer Rudyard Kipling, meticulously restored for lodging.