A six-day tour of the Berkshires in western Massachusetts

North Shore CyclistsThis scenic week-long tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut, Vermont and New York State, with 3 nights at 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 a few flat roads, rolling hills and some long steady climbs, designed for upper intermediate to advanced cyclists.

Umpachenee Falls Ride This classic Berkshire ride starts out with some easy cycling along the flat flood plain 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 theoldest 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

deerfield river, massachusetts
View from Mount Everett in the Berkshires
Twin Lakes
This beautiful 46 mile ride take 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

Twin Lakes bicycle rideWest 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

Cycling Mount Greylock Wednesday, Day 4: Over or Around Mount Greylock
In the morning drive one hour north 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 the Mount Greylock, the highest peak in Massachusetts, or continue around the mountain on the wonderfulAshuwillticook Rail Trail (the flattest ride in the Berkshires) through Cheshire and Adams. View rides:
Over Mount Greylock Around Mount Greylock
Thursday Day 5, Bennington, Vermont: In the morning we'll head 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
Bennington Monument cycling
Bennington Monument cycling Natural Bridge This short ride takes you to Natural Bridge in North Adams, where deep crevices were cut through the limestone during the last glacial era.

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, and the Clark Art Museum in Williamstown, and , and Mass MOCA (Museum of Contemporary Art) in North Adams. The Appalachian Trail passes through all of this area.

Log in or register to view our complete cue sheet directory:

Border to Boston
AMC Worcester
Boston - Cape Cod
Boston routes
Cape Cod
Central Mass.
Charles River Wheelmen
Narragansett Bay Wheelmen
North Shore
Pioneer Valley
Rail Trails
Seven Hills Wheelmen
Massachusetts cues by town


Search the Bike New England site

Bike New England, Ipswich MA Email Bike New England