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 […]
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 […]
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 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
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 […]
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 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 […]
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 […]
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 […]
Middletown Springs, VT August 3, 2019
Come ride with us and help change a life! Tour the beautiful bucolic slate valley of western Vermont and bordering NY. All net proceeds will be donated to Teen Challenge, Vt. in their continuing effort to help change lives from addiction. To register and more info visit: www.tourdeslate.org.
10th Annual Cycle the Seacoast, Portsmouth NH: May 5, 2019 - Choose from 25, 50 or 100 mile route options along the historic seacoast of New Hampshire on the first Sunday of May! Starting and ending at Cisco Brewers Portsmouth, there's something for everyone! All levels and abilities are welcome!
Tour de Minnechaug Mountain, May 5th, 2019 - Ride 8, 20 or 40 miles through the historic countryside of the New England towns of Wilbraham and Hampden. All net proceeds benefit the youth development projects of the Rotary Club of Wilbraham-Hampden.
Trek Across Maine: June 14-16, 2019 - New route, same great ride! The 35th annual Trek Across Maine is on Father's Day Weekend - June 14 – 16th, 2019. Featuring a new route for our 35th Anniversary, cycle 180 miles across the state of Maine.
