This is our guide to running in The Berkshires, an area identified by the hills of Western Massachusetts and the towns that encompass them: Stockbridge, Lee, Pittsfield, Lenox, North Adams, and Great Barrington. While these towns are rural — possessed of rolling farmland and foliage-intensive vistas — they are also known for a vibrant arts scene, punctuated with some of the most famous museums, theaters, and music venues in New England.
This is a large area and there are many back roads and trails that are terrific for running. We’ve tried to choose a few of the best spots, from across the region, aiming for variety. In Lenox, run on the meadows of Tanglewood and nearby Kennedy Park. In Stockbridge, we love the grounds of the Norman Rockwell Museum and nearby roads that Rockwell cycled on. Hilltop Orchards in Richmond has rewarding trails through fields and orchards. We’ve put together routes on some of the prettiest roads in North Adams and Great Barrington, and the more rural towns of Lanesboro and Richmond. The Greylock Scenic Byway, has some lovely sections for running and the 11-mile Ashuwillticook Rail Trail is a great off-road option.
The Berkshires is situated equidistant from Boston and New York, and a car is generally needed to get there and to get around. There is some regional transportation, and buses to/from Boston, New York, Albany, and Hartford (Pittsfield is the regional transportation center).
