Bicycle rides in the Berkshires

Cycling the Berkshires of Western Massachusetts

Berkshires to Boston, September 12-16, 2018 - Berkshires to Boston bicycle tour
Pain in the Mass bicycle ride Pain in the Mass, Amherst MA August 11, 2018 - THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy.…
Hoosic River Ride, August, 2018 - The Hoosic River Ride is a one-day event that benefits the education, research and advocacy programs of the non-profit Hoosic…
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…
Hazon ride, Falls Village, CT - The Hazon Ride & Retreat is a fully-supported ride, fundraiser, and community experience for people of all cycling levels and…
Umpachenee Falls Great Barrington to Umpachenee Falls - Hidden away near tiny Mill River, Massachusetts is a local gem, a rolling waterfall that starts as rapids about a…
Great Barrington - Philmont ride Great Barrington MA -Philmont NY: Tour of Massachusetts - Great Barrington  MA to Philmont, NY loops are provided by the Massachusetts State Bike Tour 2016. View the 76 mile ride.…
North Shore Cyclists Berkshire ride Cycling the Berkshires from Lenox, MA - These routes start from the Apple Tree Inn  in Lenox MA. Hancock Shaker Village: Soon after setting out on the 26…
Cycling around Mt. Greylock - Mount Greylock is the highest mountain in Massachusetts. In addition to the incredible ride over the mountain there is an…
Umpachenee Falls - A classic Berkshire ride, starting from the Windflower Inn in Great Barrington, MA but very near the hamlet of South…
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…
The New England National Scenic Trail - The 220 mile New England National Scenic Trail in southern New England consists of the Metacomet-Monadnock Trail, Mattabesett Trail and…
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…
Mount Greylock climb - Mount Greylock  at 3491 ft. is the tallest mountain in Massachusetts.. Notch Road from North Adams is the steeper of the…
North Berkshire cycling tour - Based at the Maple Terrace Motel in Williamstown, Massachusetts.Rides are 35-50 miles with terrain varying from the flat Ashuwillticook Rail…
Becket MA to Lenox bicycle ride Becket hill climb - A climbing ride in the Berkshires. From Lenox, Massachusetts head east for a few miles on the nice shoulder of Rt.…
Williamstown Natural Bridge bicycle ride Natural Bridge from Williamstown - This 14 mile loop to Natural Bridge from the Maple Terrace Motel in Williamstown Massachusetts starts out with a nice…
Williamstown to Bennington bicycle ride Williamstown – Bennington cycling loop - One of my favorite rides from Williamstown MA heads north across the state line to Bennington Vermont. A good starting…
Ashuwilticook Trail and back Adams MA Ashuwillticook Hill Climb - This ride heads south on the Ashuwillticook Rail Trail from its northern terminus at the Adams Massachusetts visitors center, and heads…
Sandy Brook bicycle ride Sandy Brook Ride - Pete Salomone suggested this as one of the best cycling loops in northwestern Connecticut. The ride originates in Pleasant Valley…
Pioneer Valley Century bicycle ride Pioneer Valley-Berkshire Century - This is the Northampton (MA) cycling Club 2009 century from Look Park in Northampton MA.  The ride visits the hilltowns…
Sandisfield-Stockbridge bicycle ride Sandisfield – Stockbridge Ride - Description from CTBikeRoutes: This rolling to hilly ride showcases some of the best of southern New England scenery: woods, a…
Deerfield River North Adams bicycle ride Williamstown Deerfield River Ride - Anyone who has taken Rt. 2 from North Adams to Greenfield knows that the Mohawk Trail is the most beautiful…
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 –…
Egremont bicycle ride North Egremont Ride - This ride begins at the Windflower Inn on Rt. 23 near the Great Barrington / South Egremont town line. We…
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…
Twin Lakes bicycle ride, Berkshires - This ride heads south from the Windflower Inn on Rt. 23 near Great Barrington MA on a nice flat road…
Berkshire Byways two state ride - Description from CTBikeRoutes:  This is a very scenic ride through the beautiful countryside of the Southern Berkshires, passing by farmlands…
Lenox to North Adams 2012 Mass Bike Pike Tour - The 2012 Mass Bike Pike Tour is a four day loop, starting in Great Barrington, heading through New York State…