View this year’s Massachusetts charity rides
Trails and Bicycle Paths in Massachusetts
Alewife Linear Park Cambridge, Somerville; Alewife Linear Park/Somerville Community Path 2 miles; Amesbury Riverwalk, 1.3 miles; Ashuwillticook Rail Trail 11.2 miles; Continue reading…..
Massachusetts rides by area:
- Berkshires
- North Shore
- Pioneer Valley
- Massachusetts trails and bicycle paths
- Massachusetts mountain bike rides (NEMBA)
Massachusetts rides on this site
(View additional rides by area)
A Reason to Ride, Danvers, MA - A Reason to Ride was a fundraiser to benefit cancer research at Beth Israel Deaconess Medical Center, starting from Danvers, MA, and visiting Wenham, Hamilton, Essex, Manchester by the Sea, Gloucester, Ipswich, Georgetown, Topsfield, and returning to Danvers. 2016 routes 50 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS &… Continue reading A Reason to Ride, Danvers, MA 
A Sterling Ride from Sudbury MA - This is a Charles River Wheelmen bicycle Ride. The road mark is a yellow “b” Start: Ephraim Curtis Middle School, Pratts Mill Rd., Sudbury, MA. map to start Description: The longest version of this ride circumnavigates Wachusset Reservoir clockwise through Sterling, Hudson, Stow and Marlboro. The medium ride avoids the reservoir, going north through Berlin… Continue reading A Sterling Ride from Sudbury MA 
Acton Onwards and Upwards - Start: Nagog Park is off of Rte 2A in Acton MA about 1 mile NW of its intersection with Rte 27. Park in the right side of the lot away from the store. (map to start) Description: Tour the hills of Harvard & Berlin (and a few other towns). Hit some favorites: Prospect Hill, Oak… Continue reading Acton Onwards and Upwards 
Acton-Bolton-Northborough ride - This Charles River Wheelmen tour of Bolton, Berlin and Northboro starts at the South Acton MA T station and winds and rambles on mostly very quiet back roads over moderately hilly terrain. There is an additional 39 mile route added from Bolton. The long, medium and extended short routes continue to the Fruitlands in Harvard… Continue reading Acton-Bolton-Northborough ride 
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 1875 ft. of climb over 31 miles.… Continue reading Adams MA Ashuwillticook Hill Climb AMC Boston Bike Committee Rides - AMC FG 2015-Lake Luzerne 45 Mile Ride Washington County, NY 45.1 AMC Rally 15 Mile Concord, MA 15.8 AMC Rally 16 mile ride Concord, MA 15.9 AMC Rally 29 Mile Concord, MA 29.0 AMC Boston 67 Mile Rally Ride 2013 Harvard, MA 67.4 AMC Exploring Woodstock CT Woodstock, CT 33.4 AMC FG 2015-Fort Ann Cross… Continue reading AMC Boston Bike Committee Rides
Amesbury Pawtuckaway Getaway - This is a ride that heads northwest from Amesbury MA on rural roads through some of New Hampshire’s smaller communities. The longest version enjoys some nice climbs around Mount Pawtuckaway. Thanks to DG Cycles in Epping for the inspiration– I borrowed sections from a couple of their shop rides. Start: Amesbury Elementary School, South Hampton… Continue reading Amesbury Pawtuckaway Getaway 
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… Continue reading Amherst Mass Bike Pike Tour 
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 
Amherst to Weston century ride - Several years ago we participated in the Aids Action Ride from Pittsfield to Salem MA. The map below is for the century (100 mile) ride on day 2 from U Mass in Amherst to Regis College in Weston. Start: University Drive, Amherst MA.
Assabet River Rail Trail - The Assabet River Rail Trail is a multi-use paved cycling path running through Marlborough, Hudson, Stow, Maynard, and Acton Massachusetts, following the abandoned Marlborough Branch of the Fitchburg Railroad along the Assabet River. 5.6 miles of the section from Marlborough to Maynard have been completed. Eventually the trail will be 12 miles long, extending north… Continue reading Assabet River Rail Trail 
Autumn Escape Trek, Sandwich, MA, September 25-27, 2026 - The American Lung Association Autumn Escape Bike Trek is an annual one, two, or three-day tour of Cape Cod after the summer season has passed, and is supported by more than 100 volunteers both at the start and finish lines and along the route at rest stops and intersections. Day 1 Route at RideWithGPS View and print… Continue reading Autumn Escape Trek, Sandwich, MA, September 25-27, 2026 
Bar Harbor to Boston - This 5-day, 390-mile route takes advantage of the best cycling in Maine, New Hampshire, and Massachusetts along the North Atlantic’s scenic coastline. Bar Harbor Loop Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files Day 1: Bar Harbor to Hope Route… Continue reading Bar Harbor to Boston 
Bares and the B’s from South Acton, MA - This is a Nashoba Valley Pedalers ride. Start: South Acton “T” station. (map to start) Description: Wander through Harvard, Bolton, and Berlin with the longer route heading off up Sawyer Hill to catch a few hills near Boylston. They rejoin in Berlin and take the indirect route back to Acton via Harvard. While the shorter route… Continue reading Bares and the B’s from South Acton, MA 
Bedford, MA Ride around Carlisle - This Charles River Wheelmen 28-mile ride winds through mild rolling back roads in Concord, Carlisle, Acton, and Chelmsford for those out to enjoy the scenery. Start: Parking lot of the Bedford Town Hall/High School/Library complex in Bedford Center, 7 Mudge Way, Bedford, MA View this ride at http://ridewithgps.com/routes/269948 Route at RideWithGPS View Cue Sheet from Browser Print Map from BrowserLog… Continue reading Bedford, MA Ride around Carlisle 
Bedford-Harvard MA loop - This ride goes through Concord, Acton, Littleton, Westford, Stow, and Harvard and passes an impressive array of apple orchards, while taking in a few hills. Distance: 55 miles… Continue reading Bedford-Harvard MA loop 
Berlin MA Back Roads Ride - This is the CRW “Back Roads of Switzerland” bicycle ride Start: Berlin MA, Berlin Memorial School (map to start) Description: 65 miles with 4500 ft. of climb, heading west past Wachusett Reservoir and back. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Berlin-Rutland MA ride - Start: Berlin Elementary School. 34 South Street, Berlin MA (map) This Charles River Wheelmen ride features beautiful roads, water views and other vistas on hilly roads reminiscent of Switzerland north of Worcester and near Wachusett Reservoir the communities of Berlin, Northboro, Boylston, West Boylston, Holden, Rutland, and Sterling. Route at RideWithGPS View and print cue… Continue reading Berlin-Rutland MA ride 
Best Buddies Challenge, Cape Cod, MAY 30, 2026 - Join The Best Buddies Challenge. The 100, 55, and 20-mile rides start from different locations, and all end up at Hyannisport on Cape Cod. Each route takes riders along scenic, country roads to Hyannis Port. All rides are fully supported, with rest stops along the way and support vehicles on the road. Rental bikes are also available.… Continue reading Best Buddies Challenge, Cape Cod, MAY 30, 2026 
Bicycle Rides in Massachusetts - 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.… Continue reading Bicycle Rides in Massachusetts 
Bicycles Battling Cancer, Lancaster MA, September 21, 2025 - Bicycles Battling Cancer is a fully supported one-day bike ride in support of the American Cancer Society. Every year, we have hundreds of riders sign up and fundraise for our mission to save lives, celebrate lives, and lead the fight for a world without cancer. Riders of all levels are encouraged to join and can… Continue reading Bicycles Battling Cancer, Lancaster MA, September 21, 2025 
Bikes & Beers, New Bedford, MA June 27, 2026 - Bike Ride & Beer Festival 2026 departs from CISCO BREWERS in New Bedford, MA Choose your challenge from a 15, 30, or 45-mile ride through the beautiful areas of trail and less-traveled roads surrounding South Coast Massachusetts, complete with morning fuel stations, fully marked routes, rest stops, and SAG support for all riding levels. Finish… Continue reading Bikes & Beers, New Bedford, MA June 27, 2026 
Bikes Fighting Cancer, Deerfield, MA, June 20, 2026 - Join us for the Bikes Fighting Cancer FUNdraising bike ride in Western Mass, dedicated to supporting families dealing with the burden of a cancer diagnosis and advancing cancer research. Two beautiful routes start at the very cool Tree House Brewing Company and meander through the picturesque Pioneer Valley and along the Connecticut River, featuring long… Continue reading Bikes Fighting Cancer, Deerfield, MA, June 20, 2026 
Billerica-Dunstable ride - This is a Charles River Wheelmen bicycle ride. Start: Bicknell Town Forest, Billerica, MA Description: Ride through the towns of Westford, Dunstable and Groton. The long ride adds Hollis NH, Brookline NH, and Pepperell MA. The routes are mostly quiet rolling back roads. All routes return over Lost Lake Road in Groton. 34 mile cue 42… Continue reading Billerica-Dunstable ride 
Blackstone Valley Hills and Mills - Start: Stop and Shop, 290 Turnpike Rd, Westborough MA Description: This is a hilly, 38 mile Charles River Wheelmen ride from Westborough MA& (just east of Worcester) through Upton, Northbridge, and Grafton. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Bolton North by Southwest - Start: Nashoba Regional High School is on 117 in Bolton at the intersection with Green Rd., about 3 miles west of 495. [Map] Description: A Nashoba Valley Pedalers ride. Lots of climbing, and ventures briefly into New Hampshire with route options of 70, 56, and 40 miles. Route at RideWithGPSView and print cue sheet View… Continue reading Bolton North by Southwest 
Border Run: Rhode Island from Ashland MA - This is a Charles River Wheelmen ride Start: 53 Bay Colony Drive, Ashland, MA (map to start) Description: Loops from Ashland to the Rhode Island “border”. Gently rolling hills, causeways, the Diamond Hill Reservoir in RI, quiet wooded roads. 21 mile cue, 39 mile cue, 72 mile cue Route at RideWithGPS View and print cue… Continue reading Border Run: Rhode Island from Ashland MA 
Boston to Hyannis - Start: JFK Presidential Library and Museum 100-mile route Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS & click on More to export GPS files
Boston to Provincetown - 125-Mile Ride: Boston to Provincetown: Those riders who want to challenge themselves to ride the full 125 miles will start from Boston and ride to Provincetown.Free parking in Boston will be provided at Northeastern University. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Boston to Provincetown cycling routes - The Claire Saltonstall Bikeway, or State Bicycle Route 1, is a series of bicycle paths and on-street routes that travel from Boston to both Provincetown and Woods Hole. The bikeway starts on Cape Cod at Route 3A in Bourne. It travels across the Sagamore Bridge, utilizing the bridge’s sidewalk. After the Sagamore Bridge, the bikeway… Continue reading Boston to Provincetown cycling routes 
Boston to Provincetown, MA - Start: Northeastern University, Boston, MA. This is the 125-mile former Harbor to the Bay fundraising ride. PDF Cue Sheet Route at RideWithGPS View and print cue sheet View and print the mapLog in to RideWithGPS & click on More to export GPS files
Bourne Cape Cod Ride - NARRAGANSETT BAY WHEELMEN #130 THE CAPE CAPER Description: Enjoy one of Narragansett Bay Wheelmen’s most scenic and popular rides. Ride by beaches, harbors, summer communities, bike paths, lighthouses, ponds, dunes, wetlands, woodlands, and boardwalks. Return along the Cape Cod Canal. Start: Bourne High School, Bourne MA, Cape Cod Route at RideWithGPSView and print cue sheet… Continue reading Bourne Cape Cod Ride 
Bradford Ponds and Forests - Start: Bradford Elementary School, 118 Montvale St., Bradford MA (South Haverhill) Description: This ride heads from Bradford (a historic village in South Haverhill) to nearby Groveland, then continues through Boxford State Forest on quiet local roads not often travelled on NSC routes. The short and medium rides turn back toward Bradford without crossing Rt. 114.… Continue reading Bradford Ponds and Forests 
Bruce Freeman Trail - The Bruce Freeman Trail goes through the communities of Lowell, Chelmsford, Westford, Carlisle, Acton, Concord, Sudbury, and Framingham in Massachusetts — following the 25-mile route of the old New Haven Railroad Framingham & Lowell line.. Download a PDF version of the map Download a Trail Brochure PDF
Cape Ann & North Shore Ride - The start location is Pingree School in Hamilton, MA. 100-mile ride Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS & click on More to export GPS files 60-mile ride Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS… Continue reading Cape Ann & North Shore Ride 
Cape Cod Ride - A Charles River Wheelers ride Description: Ride on lightly traveled roads with views of Cape Cod Bay, Buzzards Bay, Nantucket and Vineyard Sounds, cranberry bogs, and salt ponds. The 61 mile ride goes north to Sandwich, along the Cape Cod canal, south through Bourne, North Falmouth, Woods Hole, and along Nantucket Sound. The 41 mile… Continue reading Cape Cod Ride 
Charles River Wheelmen cue sheets - Map My Ride and Ride With GPS links for rides listed in the Charles River Wheelmen Cue Sheet Inventory. … Continue reading Charles River Wheelmen cue sheets 
Charles River Wheelmen Fall Century 2017 - This Charles River Wheelmen century ride offers 100, 62, and 50 miles through Groton, Pepperell, and Dunstable. The full century continues on back roads to Lunenberg then north along the Souhegan River to Wilton, NH, and back through Brookline, NH. Start Littleton, MA 100 miles Route at RideWithGPS View and print cue sheet View and print… Continue reading Charles River Wheelmen Fall Century 2017 
Chelmsford MA 39 Lakes - This is a Charles River Wheeelmen bicycle ride Start: Byam School, Chelmsford MA (map to start), at the intersection with the Bruce Freeman Rail Trail. Description: This ride takes you to Dunstable and passes by or near a dozen lakes in 39 miles. Route at RideWithGPS View and print cue sheet View and print map GPX… Continue reading Chelmsford MA 39 Lakes 
Chelmsford-Hollis ride - This Charles River Wheelmen ride offers a mix of suburban and rural riding, with terrain varying from gradual grades to downright hilly. The short ride hits the Towns of Chelmsford, Westford, Groton, Dunstable, and Tyngsborough. The medium ride adds a loop west and north into Pepperell and Hollis, NH. The long ride adds a scenic… Continue reading Chelmsford-Hollis ride 
Coast to the Cure, Gloucester, MA, Sept. 6, 2025 - The NF Northeast Annual Coast to the Cure ride to benefit NF Northeast at Stage Fort Park in Gloucester, MA. The ride accommodates all cycling levels. Participants will have the option to choose from 24-, 40-, or 66-mile courses. Cycle along the rolling hills of the Massachusetts North Shore—see beautiful ocean views, scenic horse and… Continue reading Coast to the Cure, Gloucester, MA, Sept. 6, 2025 
Coastal Trails Newburyport, MA - The Coastal Trails Network is a 30-mile, public system of bicycle and pedestrian trails linking the unique coastal features, town centers, neighborhoods and transportation hubs in the communities of Amesbury, Newbury, Newburyport and Salisbury, Massachusetts.
Concord heading West - Road mark The Charles River Wheelmen “Apple Pi Ride” takes you through Concord, Acton, Littleton, Westford, Carlisle, Stow and Harvard with several apple orchards, and a few hills. Start: Bedford VA Hospital, 200 Springs Rd, Bedford (map to start) Cuesheets from the CRW site: Long, Short View this ride at http://ridewithgps.com/routes/997036 Route at RideWithGPS Viewand print… Continue reading Concord heading West 
Concord Soldier Ride - Start: Minute Man National Historic Park, North Bridge Visitors Center. The Boston Soldier Ride commemorates our nation’s heroic past and present. Located in the heart of Concord, MA, the ride explores the heart of some of the Boston area’s greatest road biking country. Distance: 61 miles Route at RideWithGPS View and print map(Log in to RideWithGPS… Continue reading Concord Soldier Ride 
Concord-Boxborough loop - A Charles River Wheelmen ride Description: This ride is on mostly scenic rural roads. Starting in Concord, it makes a loop through Sudbury, Hudson, Stow, Boxborough, Littleton and Acton, Westford and Carlisle. The terrain is moderate with one notable but short climb. Start: Concord Carlisle High School Route at RideWithGPS View and print cue sheet… Continue reading Concord-Boxborough loop 
Concord-Boxborough loop - This is a Charles River Wheelmen bicycle ride circling around but not passing through the town of Maynard. The road mark is a yellow arrow and oval. Start: Concord-Carlisle Regional High School, 500 Walden St, Concord, MA. map to start Description: Favorite roads in western Middlesex County, circling around Maynard MA. A combination of rolling… Continue reading Concord-Boxborough loop 
CRW Another Side of Carlisle - This is a Charles River Wheelmen ride marked with a yellow circle and arrow. Start: Brighams Ice Cream, 46 Mill St. Arlington MA. map to start Description:; A scenic ride through the towns surrounding Carlisle including Arlington, Lexington, Bedford, Chelmsford, Acton, Westford, Concord and Lincoln. The terrain is rolling with a few hills, notably Page… Continue reading CRW Another Side of Carlisle 
CRW Fall Century, Acton MA - Charles River Wheelmen’s fall century offers three beautiful and very scenic tours through Groton, Pepperell, and Dunstable. The century route travels on back roads to Lunenberg then north along the Souhegan River to Wilton, NH, and back through Brookline, NH. The start location is the Acton-Boxborough High School in Acton, MA. Route at RideWithGPS View… Continue reading CRW Fall Century, Acton MA 
Cycle for Shelter, Haverhill MA, September 13, 2026 - The annual Cycle for Shelter to benefit Emmaus will be held at Northern Essex Community College. Cyclists can ride a 20-mile, 40-mile, 62-mile or 100-mile scenic route that will take them through Haverhill, MA, up to the seacoast of New Hampshire, and south through the North Shore of Massachusetts. Upon returning to the college, riders can… Continue reading Cycle for Shelter, Haverhill MA, September 13, 2026 
Cycle Martha’s Vineyard - Cycle Martha’s Vineyard is a recreational ride on the scenic island of Martha’s Vineyard. The 100k route circuits the island traveling along the Atlantic Ocean, Nantucket Sound, rolling farmland and State Forest. The 50k route also offers breathtaking views of Nantucket Sound and the Atlantic Ocean. All roads are paved. Cycle Martha’s Vineyard is sponsored… Continue reading Cycle Martha’s Vineyard 
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;… Continue reading Cycle Massachusetts 2015 Northampton MA 
Cycling Cape Cod and Martha’s Vineyard - Cycling Cape Cod and Martha’s Vineyard Outer Cape Rides from Ted Rowan at Cycling Cape Cod Red Brook Harbor Loop, 28 miles , Falmouth Ride, 28 miles, Cape Cod Loop, 28 miles, Upper Cape Metric Century, 62 miles Cape Cod Canal Bike Path Shining Sea Bikeway Cape Cod Rail Trail Nickerson State Park Provincelands Bike… Continue reading Cycling Cape Cod and Martha’s Vineyard 
Cycling in southeast Massachusetts - Cue sheets for the following rides are provided by Narragansett Bay Wheelmen Belchertown Central Massachusetts Spectacular Bourne, MA The Cape Caper, 22/43/62 miles Brimfield, MA Brimfield Antique Ride, 34 miles Dartmouth Larry & Ted’s Dartmouth Ride, 12/17/31 miles Dedham, MA Charles River Ride, 15/21/31 miles Dennis, MA Central Cape Cod Century, 30/45/62/100 miles Fall River,… Continue reading Cycling in southeast Massachusetts 
Cycling the Massachusetts South Shore - This Charles River Wheelmen ride is along shady, quiet roads offering great vistas of the Massachusetts shore shore coastline. The club offers this ride every week, weather permitting. The 39-mile loop includes Rockland, Hingham, Norwell, Scituate, and Cohasset The 52-mile ride adds a loop to Pemberton Point in Hull with a view of Boston Harbor… Continue reading Cycling the Massachusetts South Shore 
Dartmouth Coastal Metric Century - This Narragansett Bay Wheelmen ride starts at the University of Massachusetts campus in Dartmouth MA and heads southwest through Westport and then along the coast. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 
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 
Dorchester-Pleasure Bay ride - This short ride starts from the Thomas J. Kane Square and playground park in Dorchester MA , a residential section of Boston, and offers great views of the Pleasure Bay and Old Harbor, mostly quiet riding except for the section on Morrissey Blvd.
Distance: 11 miles… Continue reading Dorchester-Pleasure Bay ride 
Dover-Holliston ride - This is the CRW bicycle ride “In Search of Llamas” Start: Chickering School baseball field (across from Caryl Park/Noanet Woodlands Reservation) on Dedham Street in Dover, MA. (map to start) Description: Local roads from Dedham to Holliston and Sherborn MA. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX… Continue reading Dover-Holliston ride 
Dudley MA two metric centuries - These are the Day 1 and Day 2 routes for the 2016 Massachusetts State Bike Tour, starting and ending in Dudley MA. Day 1 metric century: Dudley-Burrillville-Oxbridge 62 mile ride 44 mile version 26 mile version Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course Day 2 metric century: Dudley-Putnam-Milbury loop… Continue reading Dudley MA two metric centuries 
Dudley-Woodstock MA cycling loop - This is a Seven Hills Wheelmen ride Start location: Dudley District Court, 197 Lyons Rd., Dudley MA (map to start) Route at RideWithGPSView and print cue sheet View and print mapGPX fileTCX Course
East of Amherst, MA - East of Amherst East of Amherst at RideWithGPS View Cue Sheet from Browser Print Map from Browser GPX file TCX Course
Exeter to Great Bay - What to expect: The rides go through the scenic farm country of southern New Hampshire. The terrain is rolling hills with old barns, scenic vistas, and lots of quiet roads. All the loops go by historic Kingston NH common, picturesque Newfields, Great Bay, Newmarket, and the lively college town of Durham. This ride is marked… Continue reading Exeter to Great Bay 
First Responder Ride, Boston to NYC, September 6-10, 2026 - The First Responder Ride for Resilience is a five-day Boston to New York City bicycle ride on the 25th anniversary of 9/11, honoring the 343 first responders who gave their lives. This cycling experience benefits Livestrong, Friends of Firefighters, and the Boston Fire Cancer Foundation, raising funds for the thousands more who continue to face higher rates of cancer and mental… Continue reading First Responder Ride, Boston to NYC, September 6-10, 2026 
Framingham-Milford loop - A Charles River Wheelmen Ride Description: Scenic, little-used roads through Framingham, Hopkinton, and Southborough. Hilly for longer route. Start: Nobscot Shopping Center, 776 Water St., Framingham (map) RideWithGPS Links: Route at RideWithGPS View and print cue sheet View and print map (Log in to RideWithGPS & click on More to export GPS files)
Friendship Tour, Whitinsville, MA, Saturday, June 6, 2026 - Event: 41st Annual Valley Friendship Tour Location: Ride starts/ends at Alternatives Whitin Mill, 50 Douglas Rd. Whitinsville, MA Participants are invited to walk, jog or ride through the Blackstone Valley on one of three non-competitive routes: 30-Mile cycling route (9am), a 5K walk/run (10am), or a Golden Mile walk (11am). The variety of routes means that people of all… Continue reading Friendship Tour, Whitinsville, MA, Saturday, June 6, 2026 
Great Barrington, MA -Philmont, NY Loop - 60-mile ride Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
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 West Stockbridge. Distance: 42 miles with 35-mile… Continue reading Great Barrington-Stockbridge 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. Great River Ride… Continue reading Great River Ride, Westfield, MA 
Greenville Tri-State half century - This is the 52-mile version of Narragansett Bay Wheelmen’s Tri-State Century Start: Apple Valley Mall, Greenville, RI (map to start) Description: Challenging ride in undeveloped countryside touching on Rhode Island, Connecticut and Massachusetts. Route at RideWithGPSView and print cue sheet View and print map & cue sheetGPX fileTCX Course
Habitat for Homes, Sandwich MA, September 13, 2026 - 5K to 40 Mile Scenic Routes. All ages and levels are welcome to join! Choose from 3 BIKE routes – 14, 20, or 50 miles. Choose to RUN or WALK a 5K or 10K along the Cape Cod Canal BikewayStart and end for all routes is at the US Coast Guard Station Cape Cod Canal… Continue reading Habitat for Homes, Sandwich MA, September 13, 2026 
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 
Haverhill riding north - Start: Northern Essex Community College 100 Elliott Street, Haverhill, MA (View map) Meet in the Technology center Parking Lot. Description: This ride takes us on familiar roads, some a bit hilly, and travels north of the Merrimack River into Merrimac and Amesbury, with longer rides continuing through Newton, Kingston and South Hampton in New Hampshire. Distance… Continue reading Haverhill riding north 
Holliston MA metric century - Start: 101 Summer St., Holliston, MA (map) Description: A former Cystic Fibrosis Cycle for Life route. Metric Century travels to historic Concord, MA. Route at RideWithGPSView and print cue sheet
Honey Pot Hills Orchard Ride - A Charles River Wheelmen Ride Description: A scenic ride through apple country. Description: Travel through back roads that cover Stow, Harvard, Bolton, and Berlin. Along the route, you will see beautiful views and working farms. All routes are hilly but worth the climbs for the views and descents. The medium ride will pass Bolton Orchards. Start:… Continue reading Honey Pot Hills Orchard Ride 
Hopkinton Hills Ride - A Charles River Wheelmen Ride Start: Grace Bicycles 1574 Washington Street, Holliston MA Description: The ride goes into Hopkinton, Westboro and Upton. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Impact Ride, Attleboro, MA - 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 65 miles Route at RideWithGPS View and print cue sheet View and print map Log in to RideWithGPS & click on More to export GPS files 100 miles Route… Continue reading Impact Ride, Attleboro, MA 
Ipswich-Newburyport 34-Mile Loop - This 34-mile road bike ride begins at the Hammatt St. parking lot in Ipswich, MA, and follows Rt. 1A along the coast to Newbury and Newburyport. The return is along quiet wooded roads west of Rt. 1, then taking newly-reconstructed Linebrook Road back to Ipswich. There is a short extra loop on Pine Swamp Road… Continue reading Ipswich-Newburyport 34-Mile Loop 
Kirwin/Murray Memorial Bike Ride, Falmouth MA, Sunday, October 5, 2025 - The 9th annual Kirwin/Murray Tour de Falmouth is Sunday, October 5 2025, at 8 am. The proceeds from this event benefit the Falmouth Homeless Prevention Program (FHPP) through sponsorships and registrations for this event. FHPP assists Falmouth community members in need and continues to do so with your support and generosity. Donations to the program can be made at: … Continue reading Kirwin/Murray Memorial Bike Ride, Falmouth MA, Sunday, October 5, 2025 
Lexington MA Century - This ride is from the annual Mass Bike Summer Century in 2011, starting from Lexington High School, 251 Waltham Street, Lexington, MA map. Route at RideWithGPSView and print cue sheet View and print map & cue sheetLog in to RideWithGPS & click on More to export GPS files
Lexington MA Tour de Cure, August 16, 2026 - Tour de Cure is the American Diabetes Association’s premier cycling event for all ages and abilities. All the routes will be fully supported with bike mechanics, volunteer ride ambassadors, rest stops with food and water, cheering volunteers, and more. Our post-ride festival includes lunch, music, games, a Beer Garden, and a Wellness Expo. Join the… Continue reading Lexington MA Tour de Cure, August 16, 2026 
Lexington MA: Lexington Revolutions Cycling Route - Start: Clark Junior High School in Lexington, MA. (map to start) Description: Ride the beautiful roads of Lexington, Concord, Carlisle, Lincoln, Chelmsford, and Westford. Ride by Great Brook Farm, The Olde North Bridge, Hanscom Field, horse and dairy farms. Route at RideWithGPS View and print cue sheet View and print map (Log in & click… Continue reading Lexington MA: Lexington Revolutions Cycling Route 
Lexington, MA 22-Mile Ride - START/FINISH LOCATION: Lexington High School, 251 Waltham Street, Lexington, MA 02421 Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
Lexington-Groton ride - A Charles River Wheelmen Ride Description: This 66 mile early spring ride is a chance to experience the amazing G-forces of Lost Lake Road in Groton, along with lots of rolling hills and quiet country roads. Start: Lexington Green in Lexington Center. 1903 Mass Ave, Lexington (map) Long/66 mile Short/33 mile Route at RideWithGPS View… Continue reading Lexington-Groton ride 
Linda’s Early Birthday Bicycle Ride - This is a classic bicycle ride from Charles River Wheelmen Start: Commuter rail station, 451 Auburn St., Auburndale, MA (map to start) Description: serene and lightly traveled back roads through the safe neighborhoods of Wellesley, Weston, Wayland, Sudbury, and Lincoln. The long rides add Concord. Route at RideWithGPS View and print cue sheet View… Continue reading Linda’s Early Birthday Bicycle Ride 
Massachusetts Bicycle Law - *Cyclists have the right to use all Massachusetts public ways except limited access or express state highways and where signs specifically prohibit bicycles. *Cyclists shall be subject to the traffic laws and regulations of Massachusetts. Bicycles shall not be required to be registered. *Cyclists must signal turns, but such signals shall not be required to… Continue reading Massachusetts Bicycle Law 
Massachusetts Bicycle Trails - Links to over 100 bicycle trails and bike paths from the Berkshires to the North Shore and Cape Cod.… Continue reading Massachusetts Bicycle Trails 
Massachusetts Formidable Ride - The Formidable is the toughest road ride in Massachusetts, with three routes: a 160-mile pavé ride, a century version, and a mixed-terrain ride. The Pavé 160 Mile and Pavé 100 Mile rides start at the Ride Studio Cafe, Lexington, MA. The 120-mile mixed terrain Terra Dirt Ride starts in West Brookfield, MA. 160-mile Pave’ Ride View route at RideWithGPS View and print cue sheet… Continue reading Massachusetts Formidable Ride 
Massachusetts-New Hampshire 200K - This route is provided by New England Randonneurs, starting from Lexington, MA Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files
Maynard-Harvard Hills - The Harvard Hill Climb is a Charles River Wheelmen ride Start: Akkorri Networks parking lot, Taylor St.and Foster St., Littleton. (map to start) or Littleton High School nearby. Distance: 38 miles. Route at RideWithGPS View and print cue sheet View and print map(Log in to RideWithGPS & click on More to export GPS files)
Merrimack River Ride from Ipswich MA - A ride from Ipswich, Massachusetts, through the state forest area to West Newbury, MA, along the Merrimack River, returning through Newburyport and the Great Salt Marsh. (map to start) Route at RideWithGPSView and print cue sheet View and print map & cue sheet(Log in to RideWithGPS & click on More to export files)
Middleboro MA to the Coast - This Narragansett Bay Wheelmen century ride starts at the Middlebury High School on East Grove St. in Middleboro, MA, and forms a loop through Kingston, Duxbury, Marshfield and North Scituate along the coastline south of Boston.
Distance: 93 miles.… Continue reading Middleboro MA to the Coast 
Middlesex Community College Bike Challenge - A 40-mile ride through Bedford, Carlisle, and Billerica MA (10 mile option available) Location: Bedford Campus 591 Springs Road, Bedford MA (map to start) Event Website Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Millbury MA Singletary Pond Rides - These two Seven Hills Wheelmen bicycle rides start at the corner of West Main Street and Harris Street in Millbury MA, by Singletary Pond. (Map to start) with some moderately hilly terrain. The 60 mile route circles through three states, including Spencer, Charlton, Southbridge and Dudley in Massachusetts & Thompson, Conn., and the Buck Hill… Continue reading Millbury MA Singletary Pond Rides 
Minuteman Ride, Concord, MA - The former MS Minuteman Ride visits the beautiful roads of historic Concord and the surrounding towns west of Boston. The ride has been discontinued 60 miles Route at RideWithGPS View and print cue sheet View and print mapLog in to RideWithGPS & click on More to export GPS files 25 miles Route at RideWithGPS View and print cue sheet… Continue reading Minuteman Ride, Concord, MA 
Nantucket bike rides - Deb and I celebrated her late April birthday with a trip to Nantucket, taking advantage of great early season rates at the Hotel at 21 Broad St. The ferry from Hyannis to Nantucket took about an hour, and surprisingly, we were the only people with bikes. We were fortunate to have 30 miles of paved paths to ourselves,… Continue reading Nantucket bike rides Narragansett Bay Wheelmen rides - These vintage cue sheets for Rhode Island, neighboring Massachusetts and Connecticut are provided by Narragansett Bay Wheelmen (NBW).
Nashoba Bakery Ride - Start: South Lincoln Commuter Rail Parking Area. From RT 95/128 take Rt 2 west to stop light at Tracey’s Corner Shell Station. Take Bedford Rd left or South 1.0 mile to Lincoln Center. (5 corner intersection with planter & library). Bear right on Lincoln Rd 1.5M to the South Lincoln train parking on right. A… Continue reading Nashoba Bakery Ride 
Nashoba Valley Century - The Nashoba Valley Pedalers bicycle club annually sponsors a Fall Century the first weekend after labor day. The vintage 25, 50, 75, and 100 mile routes start and finish at the Lincoln Sudbury Regional High School, 390 Lincoln St., Sudbury, MA. 2012 100 mile route 2012 78 mile route 2012 50 mile route 2012 27 mile… Continue reading Nashoba Valley Century 
Cycling New England 