Berkshire Hills Road

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. Great Barrington

   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.

   Read the complete Great Barrington write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Great Barrington is where the day begins. Next is Stockbridge.

2. 2. Stockbridge

   The long Main Street runs between old maples and white porches, with the Red Lion Inn, a sprawling clapboard hotel with a rocking-chair porch, anchoring the middle. Norman Rockwell lived and worked here from the 1950s until he died in 1978, and his painting of this very street, wrapped in snow and Christmas lights, is among his best-loved pictures. The museum that carries his name sits on a hillside just outside the village.

   Read the complete Stockbridge write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Stockbridge comes up about 13 km into the recorded legs. Next is Lenox.

3. 3. Lenox

   Lenox is a small town with a famous summer name. Tucked into the hills of the southern Berkshires, it grew in the nineteenth century into the place wealthy New Yorkers and Bostonians went to build enormous summer cottages, which they called cottages with a straight face. Edith Wharton built The Mount here in 1902, and wrote some of her best-known work while living on that hilltop. The big estates are mostly schools, inns and arts venues now, and the village centre is neat, white-steepled and a bit self-conscious, which is part of the charm.

   Read the complete Lenox write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   about 25 km into the recorded legs you reach Lenox. Next is Pittsfield.

4. 4. Pittsfield

   Pittsfield is the biggest town in the Berkshires, and for a rider it is mostly a useful hinge: an old mill and manufacturing city of forty-odd thousand people sitting in the broad Housatonic valley, with the hills of the Berkshire plateau pressing in on both sides. General Electric once ran its transformer works here and gave the town its working-class backbone, and the downtown still has the long brick blocks and the wide Park Square to prove it. For a motorcyclist, that means fuel stations on every approach, plenty of places to eat, and no fuss.

   Read the complete Pittsfield write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Pittsfield, about halfway. Next is Lanesborough.

5. 5. Lanesborough

   Lanesborough sits at the foot of the Berkshire Hills in the far west of Massachusetts, at about 350 metres, in the broad valley of the Hoosic River, with the great bulk of Mount Greylock to the east. At 1,064 metres, Greylock is the highest peak in the state, a broad, forested massif that dominates the skyline for miles, and a ride to its summit is the main reason for coming here. The town itself is a quiet, rural place of farms, old white houses and a lake, Pontoosuc, that fills with boats in summer.

   Read the complete Lanesborough write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Lanesborough sits at 58 km, late in the day. Next is Williamstown.

6. 6. Williamstown

   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.

   Read the complete Williamstown write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   The route ends here after 70 km.