Hiking in the Berkshires

Looking for great year-round outdoor activities? Look no further than the hiking trails that wind their way through the beautiful Berkshires in western Massachusetts! The trails and woods are coming alive and there’s a whole world of outdoor exploration, discovery, and family adventures to be had this year.

Whether you’re after some entry level hiking, or a weekend family excursion, the following list offers a variety of local hiking opportunities, starting with one that’s right here in Bousquet’s own backyard.

Known for its fall foliage, there is still so much to enjoy in the spring and summer. Come to the mountain and hike the Mahanna Cobble trail, with its panoramic views of Pittsfield and the northern Berkshires, and then test your legs on one of these local hikes:

Spruce Hill, Savoy

With its woodland forests, an impressive cellar foundation, and expansive views in every direction, Spruce Hill is a hike that has it all! On 10,200 sprawling acres for year-round recreation.

Mount Greylock, North Adams, Lanesboro, Williamstown

There are too many great hikes here to choose just one, so the DCR has put out  this handy list of suggested excursions for all ages and abilities. Here you will find the highest point in Massachusetts, where you can see up to 90 miles away. 

Monument Mountain, Great Barrington

Rich in literary history, Monument Mountain is perfect for all ages. Walk in the footsteps of Hawthorne and Melville, and explore the boulders, cliffs and ledges at the summit. You may even see a bald eagle across the Housatonic River Valley from the 1,642-foot summit.

Olivia’s Overlook at Yokun Ridge South, Richmond

Olivia’s Overlook is at the center of the 734-acre Yokun Ridge reserve. This popular overlook is also the trailhead for 6 miles of trails. The BNRC has produced this helpful trail map to help guide your next adventure. These lands are of great significance to the Stockbridge-Munsee Mohican Nation today.

Shaker Mountain, Hancock

Transport yourself back to the 1800s on one of the hikes along the Shaker Trail, beginning at Hancock Shaker Village. Discover the remains of a former Shaker religious settlement and sacred site.  Enjoy a moderate-strenuous ability hike. 

Old Mill Trail, Dalton

This gentle 1.5 mile out and back trail follows the east branch of the Housatonic River, includes mill ruins, and offers .7 miles of accessible trail. This trail connects the communities of Dalton and Hinsdale and combines nature’s beauty with a rich local history.

If you’re still on the lookout for great outdoor experiences this spring, fall and summer, the Berkshires has so much more to offer, so be sure to explore these local Berkshire trails, or go big and check out the Appalachian Trail in Massachusetts.