Top Berkshire Trails

A hike with a view or a stroll in the woods? Our top Berkshire trails offer a range of activities. Find the one that is right for you.

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Alford Springs

Mostly forested ridgeline for hikers, snowshoers, seasoned cross-country skiers, mountain bikers, hunters and berry-pickers.

Alford, MA
1 to 7 miles of trails
Difficulty: Moderate to difficult
Size: 899 acres
Especially good in: Winter
Special features: Blackberries in summer and noteworthy backcountry Nordic skiing in winter. Gorgeous views of Alford Valley and good hunting reported.

Explore Alford Springs

Basin Pond

Trails lead across streams and cascades through a boulder-strewn natural amphitheater to a beaver pond and the site of two long-gone man-made dams.

Lee, MA
2.5 miles of trails
Difficulty: Moderate (some stream crossings on step-stones)
Size: 296 acres
Especially good in: Summer
Special features: Beautiful wetlands, with a wildlife viewing deck. Trail crosses a boulder field--a great place for kids to climb and hide on trailside rocks.

Explore Basin Pond

Bob’s Way

Multiple loops with fabulous beaver pond views. Formerly a heron rookery still teeming with wildlife.

Monterey and Sandisfield, MA
1.75 to 2.5 miles of trails
Difficulty: Moderate
Size: 263 acres
Especially good in: Spring
Special features: A stone seat with a great view, created from bedrock ledge and artisanal stonework

Explore Bob’s Way

Clam River

A wild river with evidence of a time when the area was not so wild: traces of a dam, extensive stone walls, and an intact house foundation.

Sandisfield, MA
1.5 to 6 miles of trails
Difficulty: Easy to moderate
Size: 550 acres
Especially good in: Summer
Special features: Beautiful, romantic stream valley with old stone foundations and millworks.

Explore Clam River

Hollow Fields

Walk mowed paths through open fields with views that are both sun-splashed and windswept, stunning in all seasons.

Richmond, MA
About 6 miles of trails
Difficulty: Moderate
Size: 660+ acres
Especially good in: Spring
Special features: Open fields and scenic views great for bird watching and picnicking

Explore Hollow Fields

Hoosac Range

Ridgeline trail along the Berkshires’ northeastern wall with cool rock cliffs and several dramatic vistas: prepare for the sublime!

North Adams and Florida, MA
1.6 to 6 miles of trails
Difficulty: Easy to difficult
Size: 989 acres
Especially good in: Fall
Special features: Blueberries at Sunset Rock, awesome spring snowshoeing, and migratory raptors in fall.

Explore Hoosac Range

Housatonic Flats

The loop trail gets you up close and personal with more than a half-mile of Housatonic riverbank.

Great Barrington, MA
0.9 mile round-trip
Difficulty: Easy
Size: 26 acres
Especially good in: Spring
Special features: Birdwatching, dog walking, wildlife viewing.

Explore Housatonic Flats

Mahanna Cobble

This summit at Mahanna Cobble offers a beautiful vista where we acknowledge BNRC founder George Wislocki. Visit his stone bench and explore this northern trailhead for The High Road.

Lenox and Pittsfield, MA
3.2 miles
Difficulty: Difficult
Size: 222 acres
Especially good in: Summer/Fall
Special features: Gorgeous views south from George’s bench

Explore Mahanna Cobble

Konkapot Ridge is named for tribal leader, John Konkapot, and the connection of the Mohican people to their homelands. The Mt. Hunger trail provides vistas and a wooded ridgeline with interesting rock formations.

Tyringham, MA
1.4 miles, round trip
Difficulty: Moderate
Size: 1,728 acres
Special features: Part of the Berkshire Wildlife Linkage

Explore Mt. Hunger at Konkapot Ridge

Old Mill Trail

The Old Mill Trail is your best way to get at the upper reaches of the Housatonic River.

Dalton and Hinsdale, MA
Entire trail: 3 miles
Accessible section: 1.4 miles
Difficulty: Accessible to easy
Size: 127 acres
Especially good in: Spring/Summer
Special features: fishing access and interpretive trail

Explore Old Mill Trail

Olivia’s Overlook at Yokun Ridge South

Olivia’s Overlook is at the center of the Yokun Ridge South reserve and connects to The High Road.

Lenox, Richmond, Stockbridge, and West Stockbridge, MA
Over 6 miles of trail
Difficulty: Moderate
Size: 734 acres
Especially good in: Fall
Special features: Great views, Monks Pond, spring wildflowers, mountain laurel

Explore Olivia’s Overlook at Yokun Ridge South

Parsons Marsh

The gateway to Lenox’s Parsons Marsh, forested wetland, and quarry pond.

Lenox, MA
0.6-mile accessible trail, round-trip
Difficulty: Accessible
Size: 183 acres
Especially good in: Spring/Summer/Fall
Special features: Exceptional habitat for birding

Explore Parsons Marsh

Steadman Pond at Konkapot Ridge

A beautiful setting for excellent bass fishing, bird watching, picnicking, and swimming.

Monterey and Tyringham, MA
0.25 miles, one-way
Difficulty: Easy
Size: 790 acres
Especially good in: Summer
Special Features: Tranquil pond with seeming infinite forest beyond

Explore Steadman Pond at Konkapot Ridge

Steepletop

Ideal for year-round activities. Woods range from an unusual patch of old-growth to quite young forest, managed for wildlife that require that habitat.

New Marlborough and Sandisfield, MA
5 miles of trails
Difficulty: Easy
Size: 1,230 acres
Especially good in: Spring/Winter
Special features: Expansive wetlands, miles of wood road

Explore Steepletop

Stevens Glen

A short hike brings you to one of Berkshire County’s most dramatic sights: Lenox Mountain Brook cascading down a steep rocky ravine.

Richmond and West Stockbridge, MA
1.2 miles round-trip; 1 hour
Difficulty: Moderate
Size: 129 acres
Especially good in: Spring
Special features: A waterfall through romantic rock cleft, a viewing platform with bench for reflection, and a deep hemlock forest.

Explore Stevens Glen

The Boulders

Explore more than six miles of trails plus the dramatic boulders that give the area its name and offer a vista to the west

Dalton, Lanesborough, and Pittsfield, MA
0.5 to 7 miles of trails
Difficulty: Easy to moderate
Size: 645 acres
Especially good in: Winter, Spring, Fall
Special features: Miles of excellent trails, beautiful tall trees, and the natural slides.

Explore The Boulders

Thomas & Palmer Brook

Wind through old pasture, a wetland, and mature forest to a dramatic high point of exposed bedrock.

Great Barrington, MA
2 miles of trails
Accessible section: 0.5 miles
Difficulty: Accessible to moderate
Size: 267 acres
Especially good in: Spring/Summer/Fall
Special features: Gorgeous views across wetlands, large sugar maples, geology

Explore Thomas & Palmer Brook

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All BNRC Reserves

For more hikes and adventures, pick up BNRC’s Go Wild or ¡Disfrute BNRC! at any local brochure rack, or request one at hello@ bnrc.org or 413-499-0596. Take a moment and let us know about your walk!

Top Berkshire Trails

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