Connecticut Valley Hill Towns

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. Northampton

   Northampton is the cultural heart of the Pioneer Valley, a college town with an unusually busy centre for a place of twenty-eight thousand. Smith College, founded in 1871, sets the tone with its old brick halls, gardens and a campus that spills into the streets, and the town around it has a taste for bookshops, music venues, vegetarian restaurants and independent cinemas. It has a long-standing reputation as one of the most liberal places in New England, with a large lesbian community and a strong tradition of dissent, and the locals say it with a certain pride.

   Read the complete Northampton write-up.

   Recorded stop-planning note

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

   Planning note

   Northampton is where the day begins. Next is Conway.

2. 2. Conway

   Conway is a hill town, one of those small Massachusetts communities on the western edge of the Connecticut River valley where the land begins to fold into the Berkshires. It has under two thousand people, a white-steepled centre, a tiny library and a scatter of farms that tilt across the hillsides, and it feels remarkably far from anywhere. The South River runs through it, and the countryside is a mix of woods, meadows, orchards and old stone walls that were built by farmers clearing the fields.

   Read the complete Conway write-up.

   Recorded stop-planning note

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

   Planning note

   Conway comes up about 28 km into the recorded legs. Next is Ashfield.

3. 3. Ashfield

   Ashfield is the sort of Massachusetts hill town where the main street has a general store, a library, a town hall and a lake, and little else, and nobody sees a problem with that. It sits in the Hilltowns west of the Connecticut River, in the rolling country of Franklin County, with the Pioneer Valley down to the east and the Berkshires beginning to stack up to the west. About eighteen hundred people live here, and most of the road network around them is wooded, twisting and quiet.

   Read the complete Ashfield write-up.

   Recorded stop-planning note

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

   Planning note

   about 38 km into the recorded legs you reach Ashfield. Next is Shelburne Falls.

4. 4. Shelburne Falls

   Shelburne Falls is really two villages, Shelburne on one side of the Deerfield River and Buckland on the other, tied together by an iron bridge and a curious flower garden. The garden is on a former trolley bridge, a concrete arch built in 1908 for an electric railway that closed in the 1920s. Local women planted it in 1929, and the Bridge of Flowers now blooms from spring bulbs through the autumn, a long ribbon of colour over the river. It is a true village, with about two thousand people, some pottery and glass studios, a good bakery and a couple of cafes, and the whole thing is small enough to walk in an hour.

   Read the complete Shelburne Falls write-up.

   Recorded stop-planning note

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

   Planning note

   Shelburne Falls closes the day.