This segment is tale of two options: Very hilly, very rural (for Massachusetts) and slightly shorter Western route or a much easier Eastern route featuring lots of paths, and a visit to the picturesque college towns of Amherst and Northfield. Either way you’ll be riding through what many randonneurs consider the most scenic end enjoyable cycling in Massachsuetts, a section known as the Pioneer Valley.
Most riders will want to include the unpaved but smooth dirt road which follows the Green River from the outskirts of Brattleboro, VT to just north of Greenfield, MA. From there if riders keep heading due south (West of I-91) they’ll encounter steep rollers through particularity scenic and sparsely populated mountain towns. Alternatively, consider zig-zagging across the CT river where the terrain is nearly flat with many good quality bike path. Amherst is a great place to get a good cup of coffee and a tasty lunch.
Thing to Note
The shortest route between cities is difficult with fewer services. Most alternatives add ~5-10 miles. Ample hotels and dining options in Brattleboro, one of Vermont’s larger towns.
Westfield is the home of New Horizon Bikes which is the start/finish for the Berkshire Brevet Series and an excellent bike shop. There are only two hotels in Westfield, MA, other options require a longer ride.
Suggested RoutesAs submitted: 70 Miles, 5,500' Evaluation
Shortest option but hilly, fewer services.