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.
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 […]
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 ages. Spanning Labor Day Weekend and based at the Isabella Freedman Jewish Retreat Center. HAZON RIDE – DAY 1 2014 Route at RideWithGPS View and print cue sheet View […]
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 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 - 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. 60 mile ride Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 mile round trip from Lenox, a short climb over Lenox Mountain yields a panoramic view of Stockbridge Bowl and the craggy face of Monument Mountain. Spend a couple […]
Cycling around Mt. Greylock - Mount Greylock is the highest mountain in Massachusetts. In addition to the incredible ride over the mountain there is an easier counterclockwise loop around the mountain beginning from the same location at the Williamstown Public Library. Taking back roads through North Adams to Adams, where you’ll be on […]
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 […]
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 the Metacomet Trail and is better known as the Triple-M Trail. The network starts at Guilford, Connecticut and goes north along the Metacomet Ridge and continues through the […]
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 […]
Mount Greylock climb - Mount Greylock  at 3491 ft. is the tallest mountain in Massachusetts.. Notch Road from North Adams is the steeper of the two paved roads to the summit, with hairpin turns and some very steep sections in the first half of the climb. I prefer cycling from Williamstown to Lanesborough, […]
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 Trail to the challenging climb over Mount Greylock. Google Map for Maple Terrace Motel. Brodie Mountain / Jiminy Peak Loop with Petersburg Pass extra 7.5 mile option. This […]
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. 20, then take local roads to tiny Becket Massachusetts. The route back through New Lenox passes several of the mansions built in the Lenox area during the “gilded […]
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 climb and a view back into the town along Notch Road before dropping back down to North Adams. We ride through town, then into the extraordinary Natural Bridge […]
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 point is the Public Library in Williamstown. Rt. 7 offers a wide shoulder with a steady easy climb to North Pownal. Route at RideWithGPS View and print cue […]
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 south 10 miles to Lanesboro.Here we leave the trail for a great mix of rolling hills, climbs and descents on quiet back roads back to Adams. Total of […]
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 near Winsted CT, at Peoples StateForest.  It start out along the river for a short distance, then continues across the Massachusetts state line to Sandisfield State Forest. There […]
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 of the Berkshires, including Peru, Hinsdale, Cummington, Worthington, Ashfield, Shelburne Falls and Conway, with almost 8000 ft of climb over 99 miles of great country clubs. Start: Look […]
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 great swamp and then the sleepy village of Tyringham. After passing through this classic hamlet there are vistas of the surrounding Berkshires on your way to the well-known […]
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 drive in Massachusetts. It’s also an awesome bike ride, but the 30-40 mph descent from the Eastern Summit to Charlemont requires staying in the road, and is best […]
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 […]
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 head west to the foot of the Taconic mountains and then take back roads to North Egremont. From there, Rt. 71 to the New York state line is […]
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 […]
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 to Sheffield Make sure to stop here to view the oldest covered bridge in Massachusetts (Rebuilt and restored during the 1990’s). Continuing south, we ride through very remote […]
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 and forests, and quaint country towns. Download Cue sheet. Start:  Stop & Shop, Rt. 44,.Canaan, CT  Route at RideWithGPS View and print cue sheet View and print map […]
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 to North Adams MA, south to Lenox and returning to Great Barrington on the fourth day with some challenging rides. Day 1: Great Barrington to New Lebanon, NY […]