Greenfield is a river town of about twenty thousand in the north-west of Massachusetts, where the Deerfield and Connecticut rivers wander through a wide, farmed valley, and it is the eastern gateway of the Mohawk Trail. It is a practical, red-brick kind of place, with a long main street, a common, a good selection of diners, and shops that serve the farms of the area. Fuel, food and supplies are all easy here, so it makes a natural start.
The Mohawk Trail follows Route 2, which, according to local pride, was the first scenic highway in New England, officially dedicated as a motor road in 1914. It follows an old Native American footpath that ran between the Connecticut valley and the Hudson valley, which later served colonial settlers, soldiers and traders. The route climbs out of the valley into the Berkshire hills in a succession of curves, and the highlight is the famous hairpin turn near the summit, with a view across the valley to the Green Mountains of Vermont. The road is narrow in places, has a mix of fast and slow sections, and can be demanding on a busy day.
Along the way is Shelburne Falls, a village with a famous Bridge of Flowers, a former trolley bridge that is now covered with gardens, and glacial potholes carved in the river bed below the dam. Further west, the Hoosac Tunnel, an enormous railway tunnel bored through the mountain in the nineteenth century, nicknamed the Bloody Pit because of the deaths among its builders, lies below the road. At the western end, North Adams has a huge contemporary art museum in a former factory.
Autumn is the busy season, because New England foliage is a national spectacle and the road fills with cars from early October. The colours are spectacular, but the pace is slow, and if you prefer to ride in peace, aim for a weekday or choose a late-spring morning, when the trees are fresh and the road is clear. Summer weekends bring a lot of motorcycles, and the road has a lively social scene, with riders stopping at lookouts and roadside stands selling maple syrup.