The anchor of southwestern Vermont
Flanked by the Taconic Mountains to the west and the rolling spine of the Green Mountains to the east, Bennington County is the historic and cultural gateway to southwestern Vermont. It was one of the state’s two original counties, established in 1779, and it still carries the weight of that seniority.
It is a county defined by contrast. At the southern end lies Bennington, an industrious shire town rooted in Revolutionary War triumph, early American pottery and literary heritage. Thirty minutes north along Route 7 sits Manchester, a town of marble sidewalks, historic resort luxury, independent booksellers and deep ties to the Lincoln family. Between them rises Mount Equinox, the highest peak in the Taconic Range, standing over a landscape of covered bridges, clear rivers and preserved village greens.
It is also Vermont’s most accessible corner from the cities — closest to Albany’s airport, an easy weekend from New York, and the first Vermont many travellers ever see.
Destination overview
Where to go and how long to allow.
Old Bennington — historic and colonial: the Battle Monument, the Old First Church and the Bennington Museum. Three to four hours.
Downtown Bennington — arts and craftsmanship: Bennington Potters, the covered bridges and local cafes. Half a day.
Manchester Village — grand and historic: Hildene, the Equinox resort and marble sidewalks. A full day.
Manchester Center — retail and culture: Northshire Bookstore, outlet shopping and artisanal dining. Half a day.
Mount Equinox — alpine outdoor: the Skyline Drive, the Saint Bruno viewing centre and hiking. Two to three hours.
Arlington and Dorset — Norman Rockwell’s village and the oldest marble quarry in America, now a swimming hole. A day.
Bennington: revolutionary roots and literary giants
Bennington was where the Green Mountain Boys, led by Ethan Allen and Seth Warner, gathered in local taverns to plot the defence of their land grants — first against New York authorities and later against the British.
Rising 306 feet above the hilltop of Old Bennington, the Bennington Battle Monument is the tallest man-made structure in Vermont. It commemorates the Battle of Bennington of 16 August 1777, when Brigadier General John Stark’s American forces defeated a detachment of General Burgoyne’s army. The victory stripped Burgoyne of supplies and contributed directly to his surrender at Saratoga — the turning point of the Revolution. An elevator carries visitors to an observation level with views across Vermont, Massachusetts and New York.
A short walk away stands the Old First Congregational Church, dedicated in 1806 and among the finest examples of New England church architecture. In the adjacent churchyard lies the poet Robert Frost, alongside members of his family, his headstone inscribed with a line about his lover’s quarrel with the world.
The Bennington Museum holds the world’s largest public collection of paintings by Anna Mary Robertson Moses — Grandma Moses — who began her internationally celebrated folk-art career in her late seventies. It also displays the historic Bennington Flag, early American glass and regional pottery. Downtown, Bennington Potters has produced its distinctive stoneware since 1948 and offers behind-the-scenes tours.
Manchester: elegance, estates and outlets
Heading north on Route 7 or the scenic Route 7A brings you into Manchester, a town split into two distinct personalities: genteel Manchester Village up the hill, and the busy commercial crossroads of Manchester Center below.
Perched on a promontory over the Battenkill Valley, Hildene was built in 1905 by Robert Todd Lincoln — the only surviving child of Abraham and Mary Todd Lincoln, and president of the Pullman Company. Tour the 24-room Georgian Revival mansion, still furnished with original Lincoln family belongings including one of the president’s stovepipe hats; walk the French-inspired formal gardens, at their best when the peonies bloom in June; step inside the restored 1903 Pullman car Sunbeam; and visit the estate’s working goat dairy for a cheese tasting. Allow three hours.
The Equinox, established in 1769, is the grand resort at the heart of Manchester Village — a white-columned landmark that has hosted four US presidents as well as Mary Todd Lincoln, with a golf course, a spa, an off-road driving school and a British-style falconry school.
In Manchester Center, marble walkways laid in the 19th century connect boutiques, upscale factory outlets and two landmarks: Northshire Bookstore, one of the most celebrated independent bookshops in America, with floor-to-ceiling shelves and a whole children’s floor; and the Orvis flagship store, founded in Manchester in 1856, with casting ponds, fly-fishing schools and the adjacent American Museum of Fly Fishing.
Mount Equinox and the outdoors
Dominating the western horizon is Mount Equinox, rising 3,848 feet — the highest peak in the Taconic Range.
The Mount Equinox Skyline Drive is a 5.2-mile paved toll road that climbs from Route 7A through hairpin turns and grades reaching 12 percent, past scenic turnouts over the Battenkill Valley and the Green Mountains, to the summit. At the top, the Saint Bruno viewing centre explains the mountain’s unusual ownership: the Carthusian monks of the Charterhouse of the Transfiguration, a silent contemplative order, own much of it and maintain its conservation. On a clear day the view takes in the Green Mountains, the Adirondacks, the Berkshires and the White Mountains. For walkers, the Burr and Burton Trail climbs the eastern flank on foot from Manchester Village, gaining 2,800 feet over about three miles.
East of Manchester, the 18,100-acre Lye Brook Wilderness holds Lye Brook Falls, which drops 125 feet down mossy granite ledges — a 4.6-mile round-trip hike on an old logging railroad grade, and one of the tallest waterfalls in Vermont. The granite around it is perpetually slick; do not climb it.
And the Batten Kill, winding through Manchester and Arlington, is legendary among fly fishers for its wild brook and brown trout — clear, spring-fed and demanding. Its lower stretches through Arlington are gentle Class I paddling and tubing water.
A two-day itinerary
The classic way to see the county.
Day 1 morning — Old Bennington: the elevator to the top of the Battle Monument, then the Old First Church and Robert Frost’s grave.
Day 1 midday — the Bennington Museum for Grandma Moses, then lunch downtown.
Day 1 afternoon — Bennington Potters for a tour, then the Silk Road, Paper Mill and Henry covered bridges over the Walloomsac.
Day 1 evening — drive north on Route 7A to Manchester and dine in the village.
Day 2 morning — Hildene: the mansion, the formal gardens, the Pullman car and the goat dairy.
Day 2 midday — the Mount Equinox Skyline Drive, with lunch at the summit viewing centre.
Day 2 afternoon — Manchester Center: Northshire Bookstore, the Orvis flagship and the outlets.
Day 2 evening — fine dining at one of Manchester’s historic inns.
Practical information and where to stay
Bennington sits at the junction of Route 7 and Route 9 in the far southwest, about two hours from Albany, three from Boston and four from New York. Manchester is thirty minutes north on Route 7 or the slower, prettier Route 7A. A car is essential.
Mid-September through mid-October is the peak season, with foliage along Route 7A and the Equinox Skyline Drive among the finest in the state. The Skyline Drive closes for winter, but Manchester works as a gateway to Stratton and Bromley ski areas, and Bennington stays open and quiet year-round.
Lodging spans the range. The Equinox Golf Resort & Spa in Manchester Village runs 380 to 750 a night; the Kimpton Taconic is the upscale boutique alternative; mid-range inns like the Manchester View and the Inn at Manchester run 180 to 290; and roadside motels such as Aspen at Manchester and the Palmer House Resort start around 115. Bennington and Arlington add well-priced inns and B&Bs, and Emerald Lake State Park in Dorset offers camping. Compare live prices in the search below, with free cancellation on most rooms.
Good to know
What is Bennington County known for?+
The 306-foot Bennington Battle Monument, Vermont’s tallest structure; Robert Frost’s grave at the Old First Church; the world’s largest Grandma Moses collection at the Bennington Museum; Manchester’s outlets, Hildene and the Equinox; and the Mount Equinox Skyline Drive.
Why does the Battle of Bennington matter?+
On 16 August 1777, John Stark’s American forces defeated a detachment of General Burgoyne’s British army, stripping him of supplies and contributing directly to his surrender at Saratoga — the turning point of the American Revolution.
Where is Robert Frost buried?+
In the churchyard of the Old First Congregational Church in Old Bennington, dedicated in 1806, alongside members of his family. His headstone carries the line about having had a lover’s quarrel with the world.
What is Hildene?+
The 1905 Georgian Revival estate of Robert Todd Lincoln, the president’s only surviving child. It has a 24-room mansion with original Lincoln belongings including a stovepipe hat, formal gardens, a restored 1903 Pullman car and a working goat dairy.
Can you drive up Mount Equinox?+
Yes. The Skyline Drive is a 5.2-mile paved toll road from Route 7A climbing to the 3,848-foot summit, with grades to 12 percent. The Carthusian monks who own much of the mountain maintain it, and the summit view reaches four states.