Appalachian Trail

Ninety miles of footpaths... back country campsites... a walk in the woods... 

Worthington Balloning

An aerial nature walk... float silently above trees, ponds, rivers... a peaceful, relaxing flying experience. 

Becket Land Trust Historic Quarry and Forest

Abandoned granite quarry, extensive hiking trails, historic walk, artifacts, programs, exhibits.  Open daily, year-round. 

Berkshires Botanical Gardens

Display gardens, tropical greenhouse, woodland trail, gift shop. Open May-October. 

Bousquet Ski Resort and Summer Family Fun Center

Skiing in the Winter, Fun Park in the Summer. In Pittsfield, just ten minutes from the Winthrop Estate. 

Canterbuy Farms Cross Country Skiing

Twenty-two kilometers of groomed and tracked trails. Ski and snowshoe rentals and lessons. Ice skating and skate rentals. Warm lodge and trailside cabin. 

Catamount Ski Area

Winter ski area with the longest trail and steepest trail in the Berkshires. 

Jiminy Peak Mountain Resort

A four-season resort and activities park, with Winter Skiing and Summer Coaster Rides and Adventure Park.  

Massachusetts Department of Conservation and Recreation

Listing of public parks, campgrounds, trails, beaches, and recreational activities. Here are some links to scenic Berkshire biking routes:

http://www.housatonicheritage.org/uploaded_files/Lenox%20Bike%20Route.pdf

http://www.housatonicheritage.org/uploaded_files/Stockbridge%20Bike%20Route.pdf

http://www.housatonicheritage.org/index.php?catId=2&subCatId=57

Mohawk Trail State Forest

Scenic woodland areas on 6,456 acres with eighteen miles of rivers and steams.  Popular for fishing/swimming/hiking. Fifty-six campsites open from mid-May to mid-October.