This 233-mile tour rolls through western Massachusetts and southern Vermont. Route at RideWithGPS View and print cue sheet View and print the mapLog in to RideWithGPS & click on More to export GPS files
Western MA Tour
Category: pioneer valley
Pain in the Mass, Amherst MA
THE PAIN in the MASS TOUR was designed to help support The Tyler Foundation and the families affected by epilepsy.
Amherst Pioneer Valley Farm Ride, August 8-10, 2025
The annual Farm Ride starts from the University of Massachusetts in Amherst, MA, and offers two full days of cycling in Pioneer Valley farm country, taking beautiful back roads. Arrowed route options range from 15-100 miles and include rest stops and S.A.G. support. Visit the Farm Ride site. 100-mile route Route at RideWithGPS View and print cue… Continue reading Amherst Pioneer Valley Farm Ride, August 8-10, 2025
North FromHatfield, MA
10 MILES Route at RideWithGPS View and print cue sheet View and print map Log in to RideWithGPS & click on More to export GPS files 25 MILES Route at RideWithGPS View and print cue sheet View and print map Log in to RideWithGPS & click on More to export GPS files
Northampton Century Ride
Route provided by the Northampton Cycling Club, Northampton, MA. A challenging 104-mile loop through some of the best scenery of western Massachusetts and southern Vermont. Route at RideWithGPS View and print cue sheet View and print map(Log in to RideWithGPS & click on More to export files) 72-Mile Ride A metric century with a few extra… Continue reading Northampton Century Ride
River Valley Ice Cream Ride
Start location: Turners Falls, MA Description: The River Valley Ice Cream Ride blends the best of summertime fun – bikes, gorgeous roads, and ice cream. Three routes ranging from 10 to 50 miles offer great cycling for a range of riding abilities. Kiddie Scoop Loop seven (7) miles along the Canal Side Rail Trail in beautiful… Continue reading River Valley Ice Cream Ride
Great River Ride, Westfield, MA
Starting from Westfield near the Mass Turnpike in western Massachusetts, the Great River Ride is "one of the best century rides in the USA" according to Bicycling Magazine. With almost 9000 ft of climbing over its 102-mile course, the Great River Ride is one of the most challenging centuries in New England. View and download… Continue reading Great River Ride, Westfield, MA
Deerfield Dirt Road Randonnée, August 22, 2026
The Deerfield Dirt Road Randonnée (D2R2) was conceived in the 1990’s as just a favorite dirt-road loop in the hilltowns of Franklin County, Massachusetts. Since its birth as an organized ride 11 years ago, many have hailed D2R2 as the hardest, most beautiful, most fun, most traffic-free, most unique and overall best ride that they… Continue reading Deerfield Dirt Road Randonnée, August 22, 2026
Cycling tour of the Quabbin Reservoir
The King's Tour of the Quabbin, a Seven Hills Wheelmen RideThis Start: Barre Common, Barre MA (map to start) Club Start: Naquag Elementary School, Route 122A (Main Street), Rutland, Mass. Description: A challenging bicycle ride around the Quabbin Reservoir in the heart of Massachusetts, with several mileage options. Quabbin Reservoir was created in the 1930s… Continue reading Cycling tour of the Quabbin Reservoir
Hatfield MA, Connecticut River Valley Century
Start: Lion's Pavilion, Billings Way, Hatfield, Massachusetts Ride: Pioneer Valley Freewheelers century ride Description: This bicycle ride follows rural town roads and lightly traveled state highways . The first half heads north to Brattleboro, Vermont parallel to the Connecticut River then returns along the east side of the river. Just a few hills, and great… Continue reading Hatfield MA, Connecticut River Valley Century
Deerfield Bicycle Tour
Discover Historic Deerfield and the beautiful Connecticut River Valley from the seat of your bicycle this summer! Historic Deerfield presents a week full of handlebar-view adventures traveling the scenic byways and quiet back roads to some of the valley’s vibrant and charming communities. In addition to great cycling, this tour is rich with opportunities to… Continue reading Deerfield Bicycle Tour
Poet’s Seat climb
This ride starts at the Mt. Sugarloaf parking lot in South Deerfield MA Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 Pioneer Valley of Massachusetts to the New… Continue reading The New England National Scenic Trail
Cycle Massachusetts 2015 Northampton MA
Cycle Massachusetts State Bike Tour, “The Friendliest Ride In The East” August 1-7, 2015, Northampton, Hardwick, Greenfield; 2 nights in each location. Start and end at Smith Vocational and Agricultural High School, 80 Locust St. Northampton, MA. The Cycle Massachusetts State Bike Tour supports MassBike and better biking for Massachusetts.Saturday, August 1st Loop rides starting and ending in Northampton, MA. Three ride distances; full… Continue reading Cycle Massachusetts 2015 Northampton MA
Hatfield Connecticut Valley Century
Ride Description from CTBikeRoutes: This century ride follows mostly rural town roads, and lightly traveled state highways with good shoulders. For the first 60 miles the ride heads north to Brattleboro, Vermont, following a course west of the Connecticut River. At Brattleboro, the ride crosses to the east side of the Connecticut River and heads… Continue reading Hatfield Connecticut Valley Century
Hadley Riding the Range
Description from CTBikeRoutes: This is a rolling country ride with a couple of challenging climbs through farmlands and hills of Hadley, Amherst, Belchertown and Granby passing two beautiful waterfalls, a lovely old mill and featuring great scenic views of the Holyoke Range. Start: Hadley Village Barn Shopping Plaza, Rt. 9 Hadley, MA Cue Sheet GPX… Continue reading Hadley Riding the Range
Hadley Around the Range
Description from CTBikeRoutes: Mostly flat ride with a couple of rolling stretches around the Mount Holyoke Range through Hadley, S. Hadley, Granby, Belchertown, and Amherst, MA. Start: Hadley Village Barn Shopping Plaza, Rt. 9 Hadley, MA View this ride at http://ridewithgps.com/routes/865010 Route at RideWithGPS View Cue Sheet from Browser Print Map from Browser GPX file TCX Course
Westfield Hamptons Ride
From CTBikeRoutes This is a nice ride through the Hamptons (East, West and South) in the Pioneer Valley. Start: Southampton Road Elementary School, Route 10 & 202 in Westfield, Massachusetts. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Sunderland – Northfield loop
Description from CTBikeRoutes: This is a lovely ride through several towns in the Connecticut River Valley in Massachusetts. The ride is on mostly flat to rolling terrain and features a great snack/lunch stop overlooking the Connecticut River at a Northfield river side park. After this stop the ride route heads north up to Northfield before… Continue reading Sunderland – Northfield loop
North Amherst – Old Deerfield Ride
Description from CTBikeRoutes: This is a flat to rolling ride with great views of the Connecticut River. Stop in Sunderland to see the largest sycamore tree in Massachusetts. Enjoy lunch in historic Old Deerfield Village with its stately homes, tree lined Old Main Street, and Deerfield Academy. Mile 13.1 is the site of a former… Continue reading North Amherst – Old Deerfield Ride
Cycling New England 