The Shires

White buildings housing stores on a downtown street with green mountains behind. 
A large stone monument on a warm and sunny day.

The Shires

Set like a gem between the prongs of the Taconic and Green mountain ranges, The Shires of southwestern Vermont feel like two destinations in one. Sharing borders with both New York and Massachusetts has helped make this region an energetic crossroads of history, commerce, and culture. It’s no surprise that southern Vermont’s largest town, Bennington, is found here. At the same time, The Shires are a tranquil retreat defined by natural beauty and small-town ease—a combination that has long captivated visitors, including the family of one of America’s greatest presidents.

The Shires take their name from the fact that Bennington County has not one, but two county seats, locally known as shire towns. In the south is Bennington, where an elevator ride takes you to the top of the 306-foot Bennington Monument, the state’s tallest manmade structure. It’s a perch that offers a look back at Revolutionary War history as well as a sweeping view of today’s Bennington: a college town that hums with intellectual, artistic, and political energy. In the north is Manchester, a town made prosperous first by industry and then by vacationers hungry for fresh air, mountain vistas, and world-class fly-fishing. A testament to Manchester’s resort appeal is Hildene, a graceful hilltop estate built in 1905 by Abraham Lincoln’s son, Robert, as a summer home and now open to the public as a museum.

From these two shire towns, many smaller communities extend outward into the Valley of Vermont, filling this scenic slice of land with their own histories and highlights. Shaftsbury attracts literary pilgrims with the Robert Frost Stone House Museum, where the celebrated poet once lived and wrote some of his best-loved works. In Pownal, many hikers take their first steps on a 272-mile journey known as the Long Trail, the nation’s oldest long-distance hiking route. East Dorset is the source of the famous Battenkill River, a bucket-list destination for many anglers. Follow the river south to Manchester, and you’ll find the outdoor-sports company it inspired, Orvis, as well as the American Museum of Fly Fishing.

There is art to be discovered in The Shires, often on a scale that matches the region’s lofty peaks. The Bennington Museum boasts the largest public collection of works by Grandma Moses, while Vermont’s biggest sculpture park surrounds Manchester’s Southern Vermont Arts Center. Nature creates a masterpiece of its own in autumn, when the woodlands blaze with color around lovely Lake Shaftsbury and on the slopes of Mount Equinox, the Taconic Range’s highest summit.

Down-to-earth delights can be enjoyed in the flavors of the land itself. Pick-your-own apples come with a view at East Dorset’s Mad Tom Farm. Fresh produce fills the market at Manchester’s Earth Sky Time Community Farm, and inspires the menus at local eateries like The Restaurant at Hill Farm in Sunderland, set on a former dairy farm founded in 1779. And garlic—yes, garlic—is the hero of one of The Shires’ signature autumn events, as Bennington transforms into “Garlic Town USA” for a day devoted to sustainable agriculture, tradition, and community spirit.

Taken together—mountain majesty and valley coziness, outdoor adventure and artistic flair—The Shires are even more than a two-in-one destination. Standing at Vermont’s southwestern doorway, they offer the ultimate front porch: the kind of place where travelers can’t resist dropping their bags, settling back, and soaking it all in.

Seen from above, a tall stone monument surrounded by forests.
A painting of a red barn is presented outdoors on a sunny day next to a large sculpture of a clove of garlic.

72 Hours in Bennington

Vermont’s Shires region is a stronghold of arts, history, culture, and things to do, as well as access to bountiful outdoor recreation options. Here’s how to spend 72 hours in Bennington.