Great Barrington is the southern doorway to the Berkshires, a town of low brick buildings on the Housatonic River with a tall church steeple, a cluster of galleries and cafés, and mountains close on all sides. Its permanent population is small, but weekenders from New York and Boston swell it every summer and autumn, so that restaurants fill and the main street hums. The Berkshires themselves are not high, a worn-down range of old rounded hills, but they have a quiet grandeur, especially when mist hangs in the valleys at dawn.
The town has some unexpected distinctions. William Stanley tested an early alternating-current electrical system here in 1886, and Great Barrington is often said to have been among the first places in the United States lit by electricity in this way. W. E. B. Du Bois, the sociologist and civil rights leader, was born here in 1868, and a memorial park on the site of his boyhood home recalls him. The region also has a strong tradition of music and theatre, with Tanglewood, summer home of the Boston Symphony, a short drive north, and local barns and halls staging concerts through the summer.
For riding, the surrounding roads reward slow exploration. Route 23 wanders east through farm country and state forest toward the Connecticut line, and Route 7 runs north and south along the valley with the river alongside. Smaller lanes climb into the hills around Mount Everett and Monument Mountain, with stone walls, old orchards and sudden views over the valley. Surfaces are patched and sometimes frost-heaved, and the bends tighten without much warning. Traffic is heavy on summer weekends and fall foliage Saturdays, and light at almost any other time.
Monument Mountain, just north, is a short, steep hike with a great view, and it is where Herman Melville and Nathaniel Hawthorne met on a picnic in 1850, a moment that is said to have helped shape Moby-Dick. Shorter walks lead to waterfalls tucked into the hills.
Fuel is available in town and in Sheffield to the south, though stations thin out in the hills, so fill up first. The local farms sell cheese, cider and sweet corn, and a number of kitchens here have grown seriously ambitious. Winter brings snow and ice, and the best months are late May through October.