Featured Ride: Mount Greylock Challenge

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 360-degree 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. Get more details, turn-by-turn directions, and map in the book Road Biking Massachusetts (affiliate link).