This is one of the most challenging rides in the Berkshires, with a an ascent of several miles from South Egremont Massachusetts, riding past Mount Everett, the second highest mountain in the state to the tiny hamlet of Mount Washington, riding exactly to the end of paved roads in this corner of the Massachusetts. Here we turn toward New York State, taking an amazing descent down the winding paved road past Bash Bish Falls to the community of Copake Falls. Ride for a few miles on the paved Harlem Valley Rail Trail before cycling for several miles through New York State farm country. The ride crosses a pass in the Taconic Mountains for the return to South Egremont.This ride is approximately 40 miles. View at RideWithGPS
Start: Windflower Inn, Rt. 23 E., Great Barrington, MA 01230 , near South Egremont
Distance: 40 mi, Max Grade: 10.0 %, Elevation: Gain and descent,3400 ft
Mount Everett ride at RideWithGPS
View Cue Sheet from Browser
Print Map from Browser
View a 54 mile version of this ride that goes around Mount Everett, elevation (gain and descent) 2924 ft.
Bennington, Vermont: Ride north into Vermont through rural Pownal to Bennington, with a couple of interesting stops at the Bennington Fish Hatchery and the Hemmings Motor News Old Car Museum. After lunch, you’ll ride through three covered bridges in North Bennington, and past the farmlands of Hoosac, NY for a total of 43 miles. We recommend having dinner at Hobson’s choice in Williamstown. View ride
Natural Bridge: This 25 mile ride takes you to Natural Bridge in North Adams, where deep crevices were cut through the limestone during the last glacial era. View ride
Other Activities: During your tour, You may wish to take time to visit other Berkshire cultural highlights: The Mount in Lenox, and Kripalu yoga center in Lenox, the Clark Art Museum in Williamstown, and Mass MOCA (Museum of Contemporary Art) in North Adams. The Appalachian Trail passes through all of this area.