Bennington is the southwestern gateway to Vermont, a college and craft town of around nine thousand, set in a valley between the Green Mountains and the Taconics. The big thing you see is the Bennington Battle Monument, a tall pale tower of dolomite finished in 1891 that stands on the hill above town and can be seen from miles away. It commemorates the 1777 battle, which was actually fought a few miles west across the line in New York, when American militia defeated a British detachment going after supplies. It is a rare monument you can go up inside, with a lift to the top, and the view across three states is wide.
The old village on the hill is quieter and more graceful than the downtown below. Old Bennington has a white colonial church with a graveyard where the poet Robert Frost is buried, and his stone carries an epitaph about having had a lover's quarrel with the world. The Bennington Museum holds a large collection of paintings by Grandma Moses, along with local pottery and glass; the town has a long tradition of stoneware making, and the Bennington potters were once a name known across the country.
The riding is the reason this town sits on so many Vermont routes. Route 9, known here as the Molly Stark Trail, heads east over the Green Mountains toward Brattleboro, climbing past Hogback Mountain, with its long view from the roadside, and twisting through forest on both sides. It is a proper mountain road, with wide bends, steady gradients and a couple of tight spots where trucks come through, and it is a popular ride on any dry day. Route 7A north toward Arlington and Manchester is gentler, with the hills of the Taconic and Green ranges on either side and little villages with covered bridges close by. North Bennington has an old stone railway station and a pretty covered bridge, while Hoosick Falls over the border has the services of a small New York town.
Fuel and food are easy here, since Bennington is the largest town for some distance, with several stations on Route 7 and Route 9 and a decent selection of restaurants and cafes downtown. Autumn colour peaks around early October, and weekends then can be busy. Spring has mud and the risk of frost, while a clear summer morning is the best time of all to take the road east.