Williamstown

We nearly drove past Williamstown entirely — it’s the kind of town that announces itself with a single blinking light and a white church steeple before the road climbs back into forest — but Lia had read about the Clark Art Institute and insisted we stop. That decision reshaped our whole trip through the Berkshires. Ringed by the Taconic, Hoosac, and Green Mountain ranges, Williamstown feels less like a town than a wide clearing that Williams College and a scattering of white clapboard houses happen to occupy, mountains visible at the end of nearly every street.

The Clark and Williams College

The Clark Art Institute sits on 140 acres of pasture and reflecting pools just outside downtown, its collection of Renoirs, Sargents, and Winslow Homers housed in a white marble building that feels almost absurdly grand for a town this size. We spent a full afternoon there, then walked the museum’s own hiking trails afterward, deer grazing unbothered in the meadow below the terrace. Back in town, Williams College’s stone and clapboard buildings line Main Street and Spring Street, where we found a bookshop with a cat asleep in the window and ate dinner at a bistro packed with professors debating loudly over wine.

Mount Greylock and the Hoosac Valley

The next morning we drove the winding auto road up Mount Greylock, Massachusetts’s highest peak, where the summit’s stone War Memorial Tower looks out over five states on a clear day — we counted the Green Mountains of Vermont, the Adirondacks’ blue ridge, and the Berkshires rolling south in every direction. Coming back down, we stopped at a roadside farm stand for cider donuts and drove the Mohawk Trail east, its hairpin turns cut through hardwood forest that was already starting to blush red at the edges in early fall.

Getting There

Williamstown sits in the far northwest corner of Massachusetts, about three hours from Boston and just under three from New York City, both reached via I-90 and the winding but scenic Mohawk Trail (Route 2). The nearest airport with regular service is Albany International, about 45 minutes west across the New York border, making it the most practical option for flying in. A car is essential here — there’s no rail service, and the surrounding mountains and farm roads are half the reason to visit.