Tag: Great Barrington

Umpachenee Falls

A classic Berkshire ride, starting from the Windflower Inn in Great Barrington, MA but very near the hamlet of South Egremont. It starts out with easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland, then some gentle climbing toward Mill River, a Berkshire […]

Mount Everett- Bash Bish Falls ride

Mount Everett Climb

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 […]

Berkshire Cycle Touring

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 […]

Great Barrington-Stockbridge bicycle ride

Great Barrington-Stockbridge Ride

Alford, Stockbridge and West Stockbridge from Great Barrington, Massachusetts This ride starts on Rt. 23 at the Great Barrington – South Egremont town line, starting out with some climbs and rolling hills near North Egremont along the edge of the Taconic Mountains and continuing through tiny Alford to […]

Tyringham-Great Barrington ride

Tyringham bicycle loop

This scenic ride with 35-50 mile options starts from downtown Great Barrington Massachusetts and heads out of town up “Three Mile Hill. We circle around Lake Buel, then top to check out the Berkshire Fish Hatchery in Hartsville. Continue on to Monterey, MA, and stop for refreshments at […]