Pioneer Valley rides

Pioneer Valley trails

New England Scenic Trail 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…


Pioneer Valley Freewheelers (disbanded)

  • pioneer_vvalleyEdna Pfruit’s Hilltown Loop: Ride starts at the parking lot behind the Historical Society in the center of Williamsburg, MA., Hilly 30 miles
  • Where’s Wyben? Ride starts at the Big Y parking lot in Southampton, MA., Hilly 31 miles
  • Leverett Layout Ride starts at the Fort River School in Amherst, MA., Hilly 32 miles
  • Around the Range Ride starts at the Robsham Visitor’s Center parking lot at Umass in Amherst, MA., Rolling 33 miles
  • Northfield Ramble Ride starts at the Mt. Sugarloaf parking lot in South Deerfield, MA., Flat to Rolling 35 miles
  • Common to Common Rolling/40 miles Ride starts at the Petersham Common (intersection of Rtes 122 & 32) in Petersham, MA.,
  • Riding thru ‘Fields Ride starts at the Mt. Sugarloaf parking lot in South Deerfield, MA., Flat to Rolling 42 miles
  • Up To Wendell: Ride starts at the Hadley Elementary School on Rt 47 in Hadley, MA., Rolling to hilly (a 4 mile climb to Shutesbury) 44 miles
  • Don Maynard Memorial Guilford Connection Ride starts at the Greenfield Community College parking lot in Greenfield, MA., Rolling 45 miles
  • McCusker’s Last Stand Ride starts at the Mt. Sugarloaf parking lot in South Deerfield, MA., Rolling 46 miles
  • Backroads to Quabbin Summit Ride starts at Grossman’s Bargain Outlet Shopping Center parking lot in Chicopee, MA., Rolling 52 miles
  • Thrill of the Hill: Starts at the Post Office in Ashfield, MA (web page format). Hilly 61 miles

Rides from CT BikeRoutes

Pioneer Valley rides on this site

Farm Ride Amherst MA Amherst Pioneer Valley Farm Ride, August 18th – 20, 2017 - 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…
Pain in the Mass bicycle ride Pain in the Mass, Amherst MA August 19, 2017 - THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy. 100 miles with 6,337 ft of climbing highlighted by an 11 mile Cat. 2 climb at the midway point of the ride. Pain in the Mass 100 Route 125 miles with 7,625 ft of climbing.…
Will Bike 4 Food bicycle ride Will Bike 4 Food: Hatfield, MA: September 24, 2017 - Will Bike 4 Food offers four different routes (10, 25, 50, or 100 mile) through the beautiful Pioneer Valley, benefiting the FOOD BANK OF WESTERN MASSACHUSETTS, INC. WB4F – 10 MILE Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course WB4F – 25 MILE Route at RideWithGPS View…
Poet's Climb bicycle ride 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
New England Scenic Trail 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…
Greenfield MA bicycle ride Deerfield Dirt Road Randonnée - 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…
cycle_massachusetts 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;…
Hatfield MA century bicycle ride 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…
Hadley bicycle ride 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…
Hadley bicycle ride around 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 - Westhampton MA bicycle ride 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 bicycle ride 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…
Greenfield Amherst Old Deerfield bicycle ride 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…
Hadley MA ride Hadley MA – Mount Holyoke Loop - This ride from Hadley MA goes around Mount Holyoke. 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. Go to CT Bike Routes for cue sheet and…
Amherst to Warren bicycle ride Amherst Mass Bike Pike Tour - The Mass Bike Pike Tour is a 4-day, supported bicycle tour across Massachusetts, with daily route options of 30–65 miles. Proceeds benefit MassBike. Each year offers a different tour. This tour started from Amherst, MA. Day 1: Amherst to Warren Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course…
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 Park, Northampton, MA View the route map…
Pioneer Valley bicycle ride Tour of the Pioneer Valley - The Northampton MA cycling Club hosts the annual Tour of the Valley, Description:  Several mileage options, including a century ride. Beautiful foliage, dairy farms, and quaint villages in their classic New England splendor. All routes include scenic rolling hills of the beautiful Pioneer Valley. Start:   Look Park, Northampton, MA Route at RideWithGPS View and…
Hatfield Century bicycle ride 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…
quabbin Cycling tour of the Quabbin Reservoir - The King’s Tour of the Quabbin, a Seven Hills Wheelmen Ride This 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…
Northampton Bike Fest Northampton BikeFest - Routes provided by the Northampton Cycling Club, Northampton, MA Century Ride 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 GPX file TCX Course 72-Mile Ride A metric century with a few extra miles. A scenic…
great_river_ride Great River Ride - 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…

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