Great Outdoor Adventures

Ready for an adventure? Grab your outdoor gear and pack a picnic, the Berkshires have everything you need to satisfy a yearning for fresh air, scenic views, and a heart-pounding adrenaline rush—all set among picturesque landscapes dotted with mountains, lakes, forests, and quaint New England towns.

Berkshire outfitters such as the Arcadian Shop in Lenox offer a great selection of equipment to help furnish you with everything you need to safely enjoy the great outdoors. And if you’re looking to just rent your gear, you’ll find bikes, kayaks, and paddle boards at the ready. Knowledgeable outdoor guides from around the region can point you to the area’s best adventures, whether you want something on the beaten path—or way off.

Ashuwillticook Rail Trail, Cheshire, MA. Credit: Kindra Clineff

Looking for a walk in the woods a la Bill Bryson or Henry David Thoreau? Jump on the Appalachian Trail. More than 90 miles run through western Massachusetts, with camping along the way if you find a night under the stars appealing. Or pick a short stretch for a day hike. Properties stewarded by the Trustees of Reservations, Massachusetts Conservation and Recreation (DCR), Massachusetts Audubon, and state-owned reservations are among the many access points to Berkshire wild places and wildlife and often offer the cooling shade of towering maple, ash, and birch trees so welcome on a warm August day, or with the stunning displays of foliage in the fall.

If your idea of spending time in the trees is literally spending time in the trees, you’ll enjoy the canopy tours and ropes courses at Ramblewild and Catamount Aerial Adventure Park. And if you really want a birds-eye view of the Berkshires, climb aboard a hot-air balloon flight with Spirit Ballooning for the thrill of a lifetime.

Photo: Ogden Gigli

Looking for a place to cool down? Head for a swim in a quiet pond, a paddle on a Berkshire lake, or the refreshing spray from a walk beside a waterfall. Savor the cool and quietude of late summer and early fall evenings here, punctuated by the chirps of crickets and katydids and the twinkle of a star-filled sky. The Perseids meteor shower will be visible here starting in early August and peaking mid-month. Pull up a chair and enjoy the celestial show.

While there’s plenty to enjoy year-round in the Berkshires, these end-of-summer days and early September are perfection. Come have an adventure and check a few spots off of your bucket list!

Nancy Macy is a freelance writer and editor based in the Berkshires.