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The Trail Less Traveled

Posted on March 09, 2023Written by 1Berkshire Marketing Team
Updated on May 05, 2023

Outdoor enthusiasts flock to the Berkshires year-round, in particular for our varied, multi-use trail systems, from the rugged Appalachian Trail to pristinely paved Ashuwillticook Rail Trail. Many can be enjoyed crowd-free, such as these less-traveled suggestions.

Sheep Hill

EASY | 1.4 MI | LOOP
meadow walk, views, birding, wildflowers
Dogs, birding, river, views, wildlife
The climb to the top of Sheep Hill is well worth the effort – Instagram-worthy views of the Berkshire  mountains await! Watch for meadow birds darting over wildflowers in spring and summer, or enjoy  fiery foliage in the fall.

Mahican-Mohawk Trail

Kid-friendly, views, historic sites, wildflowers
This historic trail spans 100 miles, following the path used for centuries by Native Americans to traverse the region. Find multiple entry and exit points to craft an experience of your choosing through old  growth forest.

Greylock Glen Trails

Dogs, accessible options, kid-friendly, birding, wildlife
Visit the Glen for walking, hiking, mountain biking, snowshoeing and cross-country skiing. You’ll find a  network of multi-use trails designed to accommodate a variety of skills and interests. Plus you’ll have  access to Mount Greylock State Reservation.

Parson’s Marsh Trail

EASY | 0.6 MI | OUT & BACK
Dogs, accessible (wheelchair, stroller, kids), snowshoeing, birding, lake, views, wildlife, wildflowers
Perhaps the Berkshires’ most accessible trail, Parson’s Marsh offers half hard-packed surface and half  boardwalk that are wheelchair and stroller-friendly. Enjoy serene views of wetlands, woodlands, flora,  and fauna just outside the heart of Lenox.

Goose Pond Reservation

Birding, views, wildflowers
Goose Pond reservation protects more than a quarter-mile of rocky shoreline. On this ridge trail,
you will climb nearly 300 feet, catching glimpses of Lower Goose Pond. Find many other trails in
the area to keep exploring.

Shaker Mountain Trail

Dogs, birding, water, historic site
Located across from Hancock Shaker Village, this historic trail is great for running and hiking. You’re sure to spot ruins, crumbling stone walls, a pond and streams, as you make your way to the wooded  summit.

Willows Trail to Flag Rock

Great Barrington
EASY | 3.9 MI | OUT & BACK
Housatonic River, boulders, woods, birding
This year-round trail is beautiful in all seasons. Bring your leashed pup for a moderately challenging  stroll through the woods and over boulders – be sure to soak in the breathtaking view at the top!

Steepletop North & South Loops

New Marlborough
EASY | 2.2 MI | LOOP
Wetlands, wood road
Explore 5 miles of well-marked and maintained trails plus 3 miles of wood roads, all of which are ideal  for hiking, bird-watching, snow-shoeing and cross-country skiing. Enjoy an unusual patch of old-growth and young forests on both picturesque loops.

Race Brook Falls

HARD | 6.1 MI | OUT & BACK
Dogs, birding, views, waterfalls
You’ll gain more than 2,000 feet in elevation on this challenging wooded and rocky hike to beautiful  waterfalls. Be prepared to cross streams and wear shoes with good traction on slippery rocks. Views are worth the scramble!

Interested in hitting more Berkshire trails? Check out for the best hiking and biking trails and a complete list of Nature and Recreation opportunities, Places to StayThings to Do, and an up-to-date Events Calendar.

Photo Credits: Shaker Mountain Trail; Parson’s Marsh Trail, credit Wonders Within Reach

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