Hiking Trails & Biking Paths in The Berkshires - Where to Hike, Walk or Bicycle in Berkshire County

Hiking & Biking Trails in Berkshire County, MA

Appalachian Trail  (view trail map for entrance locations)  - Over 100 miles of this 5-state trail are in Massachusetts.  Great for day hikers or campers.


Ashuwillticook Trail (enter  at the Berkshire Mall in Lanesborough/ Route 8).  - Over ten miles of paved scenic biking or hiking trails with breathtaking views of the Cheshire reservoir and the Hoosic River.

BARTHOLOMEW'S COBBLE  Weatogue Road, Sheffield  MA  - National Natural Landmark with hiking trails along the Housatonic River and up into a high wildflower meadow with distant views.


Beartown Mountain  

69 Blue Hill Road, Monterey MA
  413/ 243 5505  - Most trails are available for Hiking, Mountain Biking, ATVs, and Horses. Boating, fishing, swimming area & sandy beach, camping sites.


Berkshire Bike Path Council  - Working to create a border to border  (75 miles) bike way route for bicyclers in the Berkshires. 


Canoe Meadows, located in the town of Pittsfield right on

Holmes Road
.  - three peaceful miles of casual trails, surrounded by wetlands and wildlife, and the Housatonic River.


Monument Mountain Trails Rte 7, Stockbridge MA   - 3 miles of moderate - strenuous (loop) hiking trails rising abruptly above the Housatonic wetlands &river valley. 1,642' summit offers northern views of Mt Greylock (near VT), and the Catskills, NY to the west. Hawks & bald eagles soar


Mount Greylock State Reservation 

30 Rockwell Rd
, Lanesborough  413 499 4262  - Hiking, camping, snowmobiling, pets allowed, hunting (seasonal). Summit Lodge,overnight accommodations, meals.  Highest elevation in Massachusetts.


Tyringham Cobble  Jerusalem Rd, Tyringham MA   - 2 miles of moderate - strenuous (loop) hiking trails, ascends through orchards & woodlands, to ancient bedrock formations.  Panoramic views of the serene Tyringham Valley, abundant wildflowers & berries.