Great Barrington Challenge Ride

West Stockbridge, Massachusetts 01266

Great Barrington Challenge Ride

Great Barrington Challenge Ride Professional Review and Guide

"The southwestern corner of Massachusetts abounds with elegant villages and fertile farmland, with views of gently rounded Mount Everett, the second-highest mountain in the Berkshires with an elevation of 2, 602 feet, in the distance.

The classic New England villages of West Stockbridge and Alford, along with the handsome commercial town of Great Barrington, add variety to the serenely rural area. And, if you like antiques, you’re in the right place—the villages of Sheffield and South Egremont boast the highest concentration of antiques shops (most of them in handsome wooden, stone, or brick houses about 200 years old) in the state. Though the Great Barrington Challenge travels along the valley ways between mountains, there’s still more than 3, 500 feet of climbing to conquer along this scenic half-century route."

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Trail Information

West Stockbridge
Nearby City
Trail Type
Moderate to Difficult
Skill Level
3 to 4 hours
Riding Time
900 feet
Trailhead Elevation
1,100 feet
Top Elevation
Discover the Berkshires Visitors Center, Pittsfield Visitors Center
Local Contacts