Williamstown is the kind of New England college town that looks as if somebody drew it for a calendar: a white-steepled church, a village green, red-brick college halls, and a ring of wooded hills all round. Williams College, founded in 1793, is the heart of it, and the Clark Art Institute, with a fine collection of Impressionist paintings, makes a good rainy-day stop. The town sits in the north-west corner of Massachusetts, a short hop from the Vermont and New York borders, and it is where the Berkshires begin to climb in earnest.
From here, the riding is some of the best in the north-east. Route 2, the Mohawk Trail, enters the town from the east after crossing the Hoosac Range, and it is among the oldest tourist roads in the country, following an ancient Native American path. The climb to the Whitcomb Summit and the hairpin turn above North Adams are the highlights, with views over the Hoosac valley and tight bends that demand a steady hand. To the south, Mount Greylock, at 1,064 metres the highest point in Massachusetts, has a narrow road to the summit with a war memorial tower on top. The road is usually closed in winter, opening around late May, so check before you go.
October is the famous month. When the maples go crimson and gold the whole region fills with visitors, traffic slows to a crawl on the Mohawk Trail, and motels book up months ahead. Come on a weekday if you can. Summer is green and warm, with cool mountain air at altitude, and early mornings are quiet and often misty. Watch for frost heaves, gravel after rain and deer at dusk, which are a real hazard on these wooded roads. Moose have returned to the area in recent decades and are best avoided in the dark.
Williamstown has a population of around four thousand, so it has fuel, a few good cafes, bakeries and a couple of inns. North Adams, about eight kilometres east, is larger and has more, along with MASS MoCA, a huge contemporary art museum housed in old factory buildings, which is worth an hour even for the unconverted. The local craft beer and maple syrup are both good, and a stack of pancakes with real maple syrup is a fine fuel for the climb.