Mount Greylock Challenge Ride

Pittsfield, Massachusetts 1201

Mount Greylock Challenge Ride

Mount Greylock Challenge Ride Professional Review and Guide

"Climb it because it is there. When you summit Mount Greylock, you will be reaching the highest point in all of Massachusetts, where you can enjoy spectacular 360degree views of the Berkshires. Unclip and climb the Veterans War Memorial at the summit to fully soak it all in. This challenging ride will bring you from Pittsfield to the summit in the first third of the ride.

After completing the brake-burning descent (which requires great care and patience), you’ll head over to Williamstown, a quaint town that is home to Williams College. The second half of the route takes you south through the valley, giving you a rest and a chance to appreciate the mountain range from a different perspective while climbing back toward Pittsfield at a more moderate pace. Plan to do the ride during the spring or summer as the Mount Greylock Scenic Byway is accessible only from mid-May through mid-October."

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Trail Information

Nearby City
Trail Type
Moderate to Difficult
Skill Level
4 to 5 hours
Riding Time
1,250 feet
Trailhead Elevation
3,500 feet
Top Elevation
The Berkshire Visitors Bureau, Mount Greylock State Reservation, Pittsfield Visitors Center
Local Contacts

Activity Feed

Jul 2018