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)
“Second Summer Cycle”, Cape Cod, Sept. 17, 2023 - Ride options will include a 30 mile Plus (30+ miles), Metric Century Plus (60+ miles), or Century route (100 miles), with starting locations in Mashpee, Sandwich and Orleans… Continue reading “Second Summer Cycle”, Cape Cod, Sept. 17, 2023 
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 Route at RideWithGPS View and print cue… Continue reading 2012 Mass Bike Pike Tour 
A Reason to Ride, Danvers MA - A Reason to Ride is 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 returning to Danvers. 2016 routes 10 mile cue sheet 25 mile cue sheet 50 mile cue sheet 50 miles Route at RideWithGPS View and… Continue reading A Reason to Ride, Danvers MA 
A scenic coastal ride from an historic New England village - This half-day ride is led by Ipswich Town Historian Gordon Harris and begins at the Ipswich Riverwalk Mural, covering about 25 miles in one of New England’s most historic and scenic coastal communities. Starting out, our ride crosses the Ipswich River pedestrian bridge to the South Green, where the historic Whipple house is located. We… Continue reading A scenic coastal ride from an historic New England village 
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 - Nashoba Valley Pedalers Onwards and Upwards short route (36 miles). 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… 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 
Acton: CRW Fall Century - The Charles River Wheelmen annual 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… Continue reading Acton: CRW Fall Century 
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 
ALA Cape Cod Autumn Escape Trek - The American Lung Association Autumn Escape Bike Trek is a 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 cue sheet View… Continue reading ALA Cape Cod Autumn Escape Trek 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 - 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… Continue reading Amherst Pioneer Valley Farm Ride 
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 Bike Trek, Plymouth MA - Location: Plymouth, MA Beneficiary: American Lung Association http://www.lung.org The American Lung Association Autumn Escape Bike Trek is a 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. 2017 Routes Day… Continue reading Autumn Escape Bike Trek, Plymouth MA 
Bares and the B’s from South Acton, MA - The Bares and the Bs 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 back in Berlin and take the indirect route back to… Continue reading Bares and the B’s from South Acton, MA 
Bedford ride around Carlisle - This Charles River Wheelmen Friday ride winds through mild rolling back roads in Concord, Carlisle, Acton and Chelmsford for those out to enjoy the scenery. The 53mi adds some hills for the fitness rider and extends through Stow, Harvard, and Littleton. Stop for food in Harvard. Shorter versions are also arrowed (18, 24 mile) The ride passes the Minuteman visitor… Continue reading Bedford ride around Carlisle 
Bedford-Harvard loop - This is a Charles River Wheelmen ride Description: The short ride goes through Concord, Acton, Littleton, Westford, and Carlisle. The long ride adds Stow and Harvard. The long ride passes an impressive array of apple orchards, while taking in a few hills. Start: Bedford VA Hospital, 200 Springs Rd, Bedford (map) RideWithGPS Links: Long Ride, Short… Continue reading Bedford-Harvard 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 - Join The Best Buddies Challenge. The 100, 50, 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… Continue reading Best Buddies Challenge, Cape Cod 
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, Marlborough MA - Join the American Cancer Society’s Bicycles Battling Cancer ride for our scenic ride through Central MA and Southern NH. Riders of all levels welcome! Choose between three route options: 30, 70 or 100 miles along a well-supported ride. Together cyclists and volunteers come together to raise funds to help save lives and provide free programs and… Continue reading Bicycles Battling Cancer, Marlborough MA 
Bike MS: Ride the Vineyard, - Bike MS: Ride the Vineyard is more than a ride. It’s an experience grounded in camaraderie and marked by passion, inspiration, determination and pure enjoyment. It will be an experience you’ll never forget, shared with new friends and old. Start/End Location: Martha’s Vineyard Regional High School, 100 Edgartown – Vineyard Haven Road, Oak Bluffs, MA 02557 Route options:… Continue reading Bike MS: Ride the Vineyard, 
Bikes Not Bombs, Jamaica Plain MA - Bike Not Bombs’ Bike-A-Thon route maps are online for all four distance options. The rides start in the Jamaica Plain neighborhood of Boston. The Bike-A-Thon offers a Century Route with options of 10 miles, 30 miles, 50 miles or 100 miles. Go to https://bikesnotbombs.org/bike-a-thon/routes. 2017 Routes 100 mile route map. 100 mile route GPX file 50 mile route map. 50… Continue reading Bikes Not Bombs, Jamaica Plain MA 
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. 12 green road, Bolton, ma [Map] Description: A Nashoba Valley Pedalers ride. Eat your heart out Hitchcock! Lots of climbing, and ventures briefly into New Hampshire with route options of 70, 56,… 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 
Border to Boston Trail - The Border to Boston Trail will provide an alternative transportation route linking communities from Salisbury to Boston. 10 miles have been completed. Border to Boston Trail map Border to Boston brochure Northern Section Newburyport Salisbury Topsfield Boxford Danvers Georgetown Newbury
Boston Best Buddies Ride - Best Buddies Challenge Riders choose from three options for distance: 100 miles, 50 miles or 20 miles. No matter what distance you choose, you’ll enjoy magnificent views biking along a classic New England route, fully supported from Boston all the way to Hyannis Port. For those who do not wish to ride, you can still… Continue reading Boston Best Buddies Ride 
Boston Hub on Wheels - This year, riders have the option of selecting either the 10-mile family-friendly route or the more challenging 40-mile course. Visit the Hub on Wheels signup page. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 
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 RideWithGPS View 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 
Brain Tumor Ride, Waltham MA - Boston Brain Tumor Ride is an event to raise awareness and much-needed resources to fund critical brain tumor-specific programs to improve the lives of all those affected by brain tumors. Hosted by the National Brain Tumor Society, the Boston Brain Tumor Ride offers individuals and teams a chance to honor and remember loved ones, connect… Continue reading Brain Tumor Ride, Waltham MA 
Bravehearts Ride, Harvard MA - Every July more than 400 cyclists (from first timers, to weekend warriors, to Olympians) brave the BraveHearts 25 or 50 mile course through the backroads and challenging hills of Harvard, Massachusetts to help fund innovative medicines and memorable experiences for families facing devastating cancer diagnoses.… Continue reading Bravehearts Ride, Harvard MA 
Bruce Freeman Trail, Chelmsford MA - The Bruce Freeman Trail is a proposed rail trail 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. Phase 1 of the Bruce Freeman Rail Trail is now open and extends 6.8 miles from… Continue reading Bruce Freeman Trail, Chelmsford MA 
Buzzards Bay Watershed Ride, Compton RI to Woods Hole MA - The Annual Buzzards Bay Watershed Ride supports the Buzzards Bay Coalition with a ride from Little Compton, RI to Woods Hole, MA… Continue reading Buzzards Bay Watershed Ride, Compton RI to Woods Hole MA 
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 
Climate Ride NE, Bar Harbor to Boston - Bar Harbor to Boston, SEPTEMBER 8 – 12, 2016 This 5-day, 390-mile Northeast Climate Ride route takes advantage of the best cycling in Maine, New Hampshire, and Massachusetts. You’ll ride along the North Atlantic’s scenic coastline by day and spend evenings with an amazing community of people. Upon registration, you will have an opportunity to choose… Continue reading Climate Ride NE, Bar Harbor to Boston 
Coastal Trails Newburyport MA - The Coastal Trails Network is an emerging 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. Construction of Phase II of the Clipper City Rail Trail and Harborwalk in Newburyport is shown in red in… Continue reading Coastal Trails Newburyport MA 
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 heart of some of the Boston area’s greatest road biking country. View the 60 mile cycling route Route at RideWithGPS View and print cue sheet… 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 
Cycle for Life, Holliston MA - Cystic Fibrosis Cycle for Life Start: 101 Summer St., Holliston, MA (map) Description: 12, 30 and 65 mile route options. Metric Century travels to historic Concord, MA. Extraordinary bike support from Landry’s Bicycle Shops. Delicious BBQ from Tennessee’s. 2012 route Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Cycle for Shelter, Haverhill MA - 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 
CYCLE Kids Breakaway Lincoln MA - With the help to the Charles River Wheelmen, CYCLE Kids hosts its second annual Breakaway Bike Ride on May 20, 2012 to raise money to get kids on bikes and on their way to living healthy, active lives. All rides leave from the deCordova Sculpture Park and Museum 51 Sandy Pond Road in Lincoln, MA,… Continue reading CYCLE Kids Breakaway Lincoln MA 
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 
Cycle Massachusetts State Bike Tour - Cycle Massachusetts is dedicated to Celebrating Cycling in Massachusetts. We organize, participate and support many other rides in Massachusetts and we are active in promoting bicycle tourism so that others will see what a great place our state is for cycling. The Cycle Massachusetts State Bike Tour supports MassBike and better biking for Massachusetts. State Bike… Continue reading Cycle Massachusetts State Bike Tour 
Cycle Massachusetts State Bike Tour - Cycle Massachusetts State Bike Tour 2018 All our proceeds go to Massbike and we are their number one donor each year – check us out at www.cyclema.com. 2018 Description Discover Central Massachusetts as we ride a loop between Amherst and Worcester. Starting and ending in Amherst – Worcester host location 3 move days. 2017 Routes Day 1 – Greenfield Routes… Continue reading Cycle Massachusetts State Bike Tour 
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
Death Ride Tour - War on ALS The Death Ride Tour/ Fall Blaze expands the popular Colorado Death Ride tour series to New England. The three-day tour rolls through western Massachusetts and southern Vermont October 6 – 9, 2017 (Columbus Day weekend). Profits support the Blazeman Foundation for ALS and the ALS Association and their research to combat amyotrophic laterals sclerosis… Continue reading Death Ride Tour 
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 - 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 
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 the section on Morrissey Blvd. Route at RideWithGPS View and print cue sheet View and print map GPX… 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 RideWithGPS View and print cue sheet View and print map GPX file TCX Course
East Coast Greenway in Massachusetts - East Coast Greenway in Massachusetts The route enters Massachusetts from the north in Salisbury, where it is primarily on-road until Boston. Heading west from Boston to Waltham, the ECG follows the Charles River Bikepath. From there, the future Mass Central Rail-Trail will take ECG users to just north of Worcester. From Worcester to the Rhode… Continue reading East Coast Greenway in Massachusetts 
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 
Food Justice Bike Ride, Greenfield MA - Start/Finish at Just Roots Community Farm, 34 Glenbrook Drive, Greenfield, MA. Two scenic courses with some hills (15 & 43 miles) with proceeds going to Just Roots Community Farm.… Continue reading Food Justice Bike Ride, Greenfield MA 
Framingham-Milford loop - A Charles River Wheelmen Ride Description: Scenic, little-used roads through Framingham, Hopkinton, and Southborough. Hilly and more so for longer route. Start: Nobscot Shopping Center, 776 Water St., Framingham (map) RideWithGPS Links: Short Route Medium Route Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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
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. Start: Windflower Inn, Rt. 23… Continue reading Great Barrington-Stockbridge 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… Continue reading Great River Ride 
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 RideWithGPS View and print cue sheet View and print map GPX file TCX Course
Hamilton MA Tour de Cure - This is the 2010 version of the North Shore 100 Mile Gran Fondo (Century Ride)sponsored by the American Diabetes Association. The start location was Pingree School in Hamilton, MA. Note that the tour now starts from the Topsfield Fairgrounds. 100 mile ride Route at RideWithGPS View and print cue sheet View and print map GPX file… Continue reading Hamilton MA Tour de Cure 
Harbor to the Bay (H2B) - The H2B Ride is a 125 mile ride from Boston to Provincetown to support people living with HIV and AID. Start: Northeastern University, Boston MA PDF Cue Sheet Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course
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 
Honey Pot Hills Orchard Ride - A Charles River Wheelmen Ride Description: A scenic ride through apple country. Description: Ttravel 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.… 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 - Join some of the best cycling in southeastern New England with the IMPACT Ride. Proceeds go to the fight against breast cancer.
Location: Attleboro MA… 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 - Falmouth Housing Corporation honors Peter Kirwin and Bob Murray, two champions of homelessness prevention and access to affordable housing in Falmouth. The Kirwin/Murray Memorial Bike Ride route follows the Falmouth Marathon route for about 29 miles, beginning at the Surf Drive Beach House. The shorter route will begin one half hour after and progress from… Continue reading Kirwin/Murray Memorial Bike Ride, Falmouth MA 
Lancaster MA cycling loops - June 10, 2012: American Cancer Society’s 4th Annual Bicycles Battling Cancer. The 2012 BBC event will start and finish at the Bolton Fairgrounds in Lancaster MA, and will feature three “loop” route options –century (100 miles), metric century (62 miles) and “lite” (30 miles). Riders may participate individually or as a team. The registration fee… Continue reading Lancaster MA cycling loops 
Lancaster Sugar House Ride - This 52 mile Seven Hills Wheelmen “Sugar House Bicycle Ride” starts at the Lancaster (MA) Middle School, intersecton of Rts 70 & 117 in Lancaster, MA. (map to start). The terrain becomes hillier and steeper as you cross into New Hampshire. At mile 27 in the middle of a five mile climb, stop at Parkers… Continue reading Lancaster Sugar House Ride 
Lexington MA Tour de Cure, August 20th, 2023 - 15-mile, 30-Mile, 62-Mile, 100-Mile Routes. Start: Lexington Labs 10 Maguire Road, Lexington, MA… Continue reading Lexington MA Tour de Cure, August 20th, 2023 
Lexington MA: Lexington Revolutions cycling tour - Lexington Revolutions is a CRW bicycle ride. Road mark is a yellow “slingshot”. Start: Clark Junior High School in Lexington, MA. (map to start) Description: Ride 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. 17 mile cue,… Continue reading Lexington MA: Lexington Revolutions cycling tour 
Lexington Mass Bike Summer Century - The annual Mass Bike Summer Century and Family Ride was Saturday, July 30, 2011, starting from Lexington High School, 251 Waltham Street, Lexington, MA map. All rides (12, 22, 45, 62 and 100 miles) traverse the heart of American Revolutionary history, from Paul Revere’s Ride through Lexington and Concord and to nearby battlefields. Longer rides… Continue reading Lexington Mass Bike Summer Century 
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’ rights and responsibilities, from the Massachusetts Bicycle Law of 2008 *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… 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 
Bike New England 