Skip to content


Chesterfield Massachusetts

The Town of Chesterfield Massachusetts is a serene town in the southern Berkshire Hills, where the production of Merino wool was historically a major industry. Many visitors come to see dramatic Chesterfield Gorge, a Trustees of Reservation property. There are miles of trails to enjoy at Chesterfield Gorge and it’s a beautiful spot in both summer and winter.

Chesterfield Gorge, Chesterfield MA
Chesterfield Gorge


The center of Chesterfield, Massachusetts.
The center of Chesterfield, Massachusetts.\

Chesterfield Wilderness Adventures/ Hilltown Sleddogs has a unique winter offering… dogsled rides! Visitors can imagine themselves Iditarod competitors while they enjoy a wild ride! You can also “hike with a husky”, attend dogsled races, as well as dog sled camps in summer to round out their year-round offerings.

The Chesterfield General Store is set to re-open in Fall 2018.
The Chesterfield General Store.


The Big News in town is that the Chesterfield General Store is reopening after a five-year hiatus. New owner Greg Monette of West Chesterfield told the Daily Hampshire Gazette that reopened a new and improved version of the store just before the holidays in 2018. It’s open now from Thursday-Sundays.

“We are bringing back the general store and adding a café space and expanding the kitchen and prep area to accommodate catering.”  Exciting news!

Chesterfield, Mass Hidden-Hills, Massachusetts
Chesterfield, Mass.

Our Chesterfield Listings