This scenic self-guided week-long tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut, Vermont, and New York State. These routes begin from the Windflower Inn in Great Barrington, MA, and two nights at the Maple Terrace Motel in Williamstown, MA. Daily Ride options are 30-45 miles, with a nice mixture of flat roads, rolling hills, and some long steady climbs, designed for upper intermediate to advanced cyclists.
Umpachenee Falls Ride: This classic Berkshire ride starts with some easy cycling along the flat floodplain of the Housatonic River through Sheffield farmland to Umpachenee Falls. The return includes an exhilarating downhill ride back to the Housatonic River before returning to Sheffield, where you may want to stop by the oldest covered bridge in Massachusetts. This ride is approximately 35 miles.
We recommend dinner at the Old Mill Restaurant in nearby South Egremont. While in the area, see what’s happening at the Mahaiwe Theater Performing Arts Center in downtown Great Barrington. View Ride.
Twin Lakes: This beautiful 46-mile ride takes us past Twin Lakes and continues to Falls Village, Connecticut. The entire route is on quiet back roads and is relatively gentle, with just a couple of short climbs. On the return, stop to visit Bartholomew’s Cobble, an unusual limestone formation with plants and ferns that are generally found several hundred miles north of this area. View Ride
Alford, West Stockbridge and Stockbridge: Ride north along the edge of the Taconic Mountains and through tiny Alford to West Stockbridge, where you can visit Baldwin’s General Store and Hoffman Pottery. The ride continues on to Stockbridge, MA, home of Norman Rockwell Museum. and Chesterwood, the studio of Lincoln Monument sculptor Daniel Chester French. The return is along the rapids of the Housatonic River to Great Barrington and back to the inn, 35 miles with extra loop options. View Ride
This is one of the most challenging rides in the Berkshires, with 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 through New York State farm country for several miles. 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, 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
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NORTH BERKSHIRE
Over or Around Mount Greylock: Drive one hour north from Great Barrington to charming Williamstown MA, “the village beautiful”. After checking in to the Maple Terrace Motel, ride to Lanesborough, where you’ll have the choice to take on the 10-mile climb to the summit of Mount Greylock, the highest peak in Massachusetts, or continue around the mountain on the Ashuwillticook Rail Trail (the flattest ride in the Berkshires) through Cheshire and Adams.
View rides: Over Mount Greylock; Around Mount Greylock
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, 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.
Bike New England 
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