South Berkshire tour from Great Barrington, MA

This weekend tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut and New York State. All routes begin from the Windflower Inn near the Great Barrington / South Egremont town line.  Daily Ride options are 30-45 miles, with a nice mixture of a few flat roads, rolling hills and some long steady… Continue reading South Berkshire tour from Great Barrington, MA

Great Barrington to Umpachenee Falls

Umpachenee Falls

Hidden away near tiny Mill River, Massachusetts is a local gem, a rolling waterfall that starts as rapids about a half mile uphill and opens up to a scenic array of water plunging over rock ledges. This small town park makes a great half day cycling destination from Great Barrington, the largest community in the… Continue reading Great Barrington to Umpachenee Falls

Bicycle rides in Massachusetts

Bicycle rides in Massachusetts

Massachusetts is home to Bike New England, with with over a hundred rides from the Berkshires to the North Shore, and many more routes shared by local cycling organizations.

Great Barrington MA -Philmont NY: Tour of Massachusetts

Great Barrington - Philmont ride

Great Barrington  MA to Philmont, NY loops are provided by the Massachusetts State Bike Tour 2016. View the 76 mile ride. 60 mile ride Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

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 hill town, to Umpachenee Falls. On our… Continue reading Umpachenee Falls

Mount Everett Climb

Mount Everett- Bash Bish Falls ride

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… Continue reading Mount Everett Climb

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 30-45 miles, with a nice mixture of… Continue reading Berkshire Cycle Touring

Great Barrington-Stockbridge Ride

Great Barrington-Stockbridge bicycle 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 West Stockbridge. Start: Windflower Inn, Rt. 23… Continue reading Great Barrington-Stockbridge Ride

Tyringham bicycle loop

Tyringham-Great Barrington ride

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 the Monterey General Store. The full continues… Continue reading Tyringham bicycle loop