10 Hiking Trails in Berkshires That You Shouldn't Miss

March 4, 2022 Harland Bartelt

The Berkshires are home to an impressive collection of cultural and historic sights. Get your fill of music, art and theater at Tanglewood, the Boston Symphony's summer home, MASS MoCA, the country's largest contemporary art center, the Norman Rockwell Museum and the Williamstown Theatre Festival. Recreational opportunities also abound, including snowshoeing, snowboarding, skiing, rafting, kayaking, fishing and golf. The Berkshires are an easy drive, just two and a half hours from Boston and New York.
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1. Ashuwillticook Rail Trail

Adams, MA 4997003 http://www.mass.gov/eea/agencies/dcr/massparks/region-west/ashuwillticook-rail-trail.html
Excellent
83%
Good
14%
Satisfactory
1%
Poor
1%
Terrible
1%
Overall Ratings

5.0 based on 159 reviews

Ashuwillticook Rail Trail

Reviewed By lupaglupa - Albany, United States

The Ashuwillticook rail trail is a well made and well maintained trail that goes by lovely scenery and has good facilities. There are numerous access points with parking, lots of benches and picnic tables, and interesting markers with information along the route. We biked the path and thought it was great. We saw lots of walkers and runners using the trail too. It's nice and wide so passing other people was never a problem. We especially enjoyed the section of the trail north of Cheshire which passes through a wetlands. The southern section, while having pretty views of the Cheshire reservoir, was a bit noisy from the nearby road traffic. Still - a great place to explore.

2. Race Brook Falls

Route 41, Sheffield, MA
Excellent
77%
Good
23%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 22 reviews

Race Brook Falls

Reviewed By Flintstone1234 - Simsbury, United States

This is a beautiful hike that includes two awesome waterfalls. There is a tiny parking lot that holds approx. 10 cars. It is at 716 S. Undermountain Rd; Sheffield, MA. The trail starts with an easy 0.2 mile walk from the parking lot to a fork. To the right of the fork is a fairly steep 0.3 mile hike to the "first falls". The last 0.1 mile gets a little confusing since some trees are down. Just keep going in approximately the same direction (or aim for the sound of the waterfall). It's a beautiful view of the waterfall from the bottom, or one can go a bit farther and climb some very difficult boulders to go higher. Starting back at the fork 0.2 miles from the parking lot, the left trail goes to the "upper falls". It is approx. 1.0 miles from the fork to the falls. It is a steep, bumpy hike, crossing the river a few times. After the first river crossing the trail makes a "U" turn to the left immediately after the crossing. After reaching the falls, one can continue approx. 0.5 miles to the campsite, then another 0.2 miles to the intersection with the Appalachian Trail (AT). It's a total of approx. 1.9 miles from the AT to the parking lot.

3. Dry Hill

Old North Road, New Marlborough, MA 01230 [email protected] http://www.thetrustees.org/places-to-visit/berkshires/dry-hill.html
Excellent
50%
Good
25%
Satisfactory
25%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 4 reviews

Dry Hill

Wander across more than 200 acres of forest and through a maze of thickets on a trail that traces a small brook and passes vernal pools and other wetlands.

4. Questing

New Marlborough Hill Road, New Marlborough, MA 01230 +1 413-298-3239 [email protected] http://www.thetrustees.org/places-to-visit/berkshires/questing.html
Excellent
57%
Good
14%
Satisfactory
29%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 7 reviews

Visit a landscape of returning forest and wetlands, and remnant cellar holes and stone walls that recall a long-abandoned settlement dating to early Colonial times.

Reviewed By JulianaS1982 - Westborough, United States

We enjoyed this hike immensely. When we went there were no other people on the trail. Because we were there when ice and snow were still on the ground we were happy we had hiking poles. We did the complete hike- the climb, the meadow and the loop (loved the old stone walls, and make sure you read about the history of this site!) and it took us a little under 2 hours. Lots of animal prints in the snow. Great spot!

5. Appalachian Trail

Massachusetts Ave, North Adams, MA 01247
Excellent
50%
Good
50%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 8 reviews

Appalachian Trail

6. Hoosac Range Trail

2599 Mohawk Trail, North Adams, MA
Excellent
50%
Good
33%
Satisfactory
17%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 6 reviews

Hoosac Range Trail

Reviewed By k6teacher - Andover, United States

The climb up to this trail may be the most challenging part - once you're up, you gently climb and descend. Take the trail all the way to Spruce Hill for great views to the west. It;s a little confusing when you get there - sheer rock on your gith, but keep folowing the trail up and you'll come to the USGS medallion in the rock on the top of Spruce Hill. We hiked it on a Sunday and passed very few people. The distances posted seemed to underestimate the true distances, but it took us about 3.5 hours from Route 2 to Spruce Hill and back, including a 15 minute break at the top.

7. Money Brook Trail

Mount Greylock, Williamstown, MA
Excellent
67%
Good
33%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 3 reviews

Money Brook Trail

8. Housatonic Flats

Route 7, Great Barrington, MA 01230 http://www.bnrc.net/item/housatonic-flats/
Excellent
25%
Good
25%
Satisfactory
50%
Poor
0%
Terrible
0%
Overall Ratings

4.0 based on 4 reviews

Housatonic Flats

Reviewed By leonards599 - Stockbridge, United States

See the Housatonic close-up. Easy walk very close to Great Barrington and really close to good food and beer.

9. Housatonic River Walk

195 Main St, Great Barrington, MA 01230-1602 http://www.gbriverwalk.org
Excellent
26%
Good
32%
Satisfactory
31%
Poor
9%
Terrible
2%
Overall Ratings

3.5 based on 117 reviews

Housatonic River Walk

Reviewed By RJBLH - South Ozone Park, United States

Just steps off Main street, you can stroll along the Housatonic River and make your way back into downtown

10. Project Native

342 N Plain Rd Route 41, Housatonic, MA 01236-9741 +1 413-274-3433 http://www.projectnative.org
Excellent
33%
Good
33%
Satisfactory
0%
Poor
0%
Terrible
34%
Overall Ratings

3.5 based on 3 reviews

Project Native

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