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.
The good riding starts the moment you leave. North of the city, Route 7 slides up the valley toward Lanesborough and Williamstown with Mount Greylock filling the windscreen. At 3,491 feet, Greylock is the highest point in Massachusetts, and its summit road, which climbs from Lanesborough, is a narrow twisty ribbon with a war memorial tower at the top. The road is only open in the warmer months and the weather up there can change in minutes, so check before you go. West of town, Route 20 and the back roads over the hills toward New York state give you the kind of New England riding that works on any day: modest climbs, wooded corners, stone walls and the odd glimpse of a farm pond.
Herman Melville lived at Arrowhead on the edge of Pittsfield in the 1850s and, the story goes, looked out at Greylock's long back while writing Moby-Dick, seeing a whale in the ridge. Whether or not it is true, the profile of the mountain does look like something large rising from a green sea. The Berkshires also became a summer playground for rich New Yorkers in the Gilded Age, and the music, theatre and dance at Tanglewood and Jacob's Pillow carry on that heritage.
Autumn is the headline season here, and justifiably. Late September into October the maples go red and orange, and the roads fill with leaf-peepers, which means slow cars and cautious corners. Midweek mornings are the answer. Spring is muddy and quiet, summer is warm and humid with afternoon thunderstorms, and winter closes the high roads.
Come to Pittsfield for a proper lunch and a full tank, then spend the rest of the day on the hills around it.