Brattleboro sits in the southeast corner of Vermont, on the Connecticut River, and it is a place with real character, a town of about seven thousand people that feels bigger because of its energy. It was the site of the first permanent English settlement in Vermont, at Fort Dummer, built in 1724 as a frontier defence against raids from the north. The town grew as a trading point on the river, and in the nineteenth century it became known for the Estey Organ Company, which at its peak was one of the largest producers of reed organs in the world, shipping instruments to parlours across America.
The writer Rudyard Kipling lived near Brattleboro for a few years in the 1890s, after marrying an American woman from the town, and while here wrote parts of The Jungle Book and Captains Courageous. He built a house on a hillside north of town, which survives and can be rented, and left after a family quarrel and a spell of harsh Vermont winters. The anecdote is a favourite of local guides.
Today the town is known for its artists, its independent shops and its food. The main street is a steep, handsome run of old brick buildings, with galleries, bookstores and cafés, and a large food cooperative is a point of civic pride. In June the town holds a lively parade of heifers, and the farmers' markets are among the best in New England. A walk by the Retreat Meadows, a quiet backwater of the river, makes a good break.
For riders, Brattleboro is a gateway. Route 9, the Molly Stark Trail, climbs west over the Green Mountains toward Bennington, in a series of bends through the forest that tighten as you gain height. Route 30 follows the West River valley northwest, with lovely open farmland and covered bridges. The Connecticut River road itself is a broad, relaxed route with views over the water to New Hampshire and the green hills beyond.
Fuel and food are easy in town, and there is also a good choice of local beer and cider. In autumn the leaves are spectacular, and the roads fill with visitors, while winter can close the mountain passes or turn them icy. Late spring and early summer are fresh and green.