Hilltowns Loop · 8A, 116 & 112

The hilltown curves in a single loop: you leave Shelburne Falls on MA-2 to Charlemont, climb MA-8A along the Chickley River to West Hawley, continue on MA-116 to Plainfield and Ashfield, and come back on MA-112 through Buckland. It's 38 miles of two-lane roads with steady curves, up and down across the plateau. Shelburne Falls is the base for coffee and food. The pavement is patched and the shoulders are narrow: a pack pace, not a race.

The hilltowns are the small farm towns on the plateau between the Connecticut River valley and the Berkshires, settled in the 1700s and never grown much since: Hawley, Plainfield and Ashfield have fewer people today than they did in the 1800s. Hawley had 881 residents in 1850 and has about 350 now. That's why the roads stay empty, with stone walls, sugarhouses and long views across the hills between villages.

Shelburne Falls, where the loop starts and ends, is the place to eat, with the Bridge of Flowers over the Deerfield River and the glacial potholes below the dam. Ashfield, halfway around, sits next to a small lake; it had 1,832 residents in 1830 and 1,695 in 2020. Services are scarce on the plateau and close early, so fuel in Shelburne Falls, and in October plan the ride around daylight.