Bicycle rides in Massachusetts

 Berkshires

Berkshires to Boston, September 12-16, 2018 - Berkshires to Boston bicycle tour
Pain in the Mass bicycle ride Pain in the Mass, Amherst MA August 11, 2018 - THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy.…
Hoosic River Ride, August, 2018 - The Hoosic River Ride is a one-day event that benefits the education, research and advocacy programs of the non-profit Hoosic…
South Berkshire tour from Great Barrington, MA - This weekend tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut and New York State. All…
Hazon ride, Falls Village, CT - The Hazon Ride & Retreat is a fully-supported ride, fundraiser, and community experience for people of all cycling levels and…
Umpachenee Falls Great Barrington to Umpachenee Falls - Hidden away near tiny Mill River, Massachusetts is a local gem, a rolling waterfall that starts as rapids about a…
Great Barrington - Philmont ride Great Barrington MA -Philmont NY: Tour of Massachusetts - Great Barrington  MA to Philmont, NY loops are provided by the Massachusetts State Bike Tour 2016. View the 76 mile ride.…
North Shore Cyclists Berkshire ride Cycling the Berkshires from Lenox, MA - These routes start from the Apple Tree Inn  in Lenox MA. Hancock Shaker Village: Soon after setting out on the 26…
Cycling around Mt. Greylock - Mount Greylock is the highest mountain in Massachusetts. In addition to the incredible ride over the mountain there is an…
Umpachenee Falls - A classic Berkshire ride, starting from the Windflower Inn in Great Barrington, MA but very near the hamlet of South…
Mount Everett- Bash Bish Falls ride Mount Everett Climb - This is one of the most challenging rides in the Berkshires, with a an ascent of several miles from South…
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…
Berkshire Cycle Touring - This scenic self-guided week-long tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut, Vermont and New…
Mount Greylock climb - Mount Greylock  at 3491 ft. is the tallest mountain in Massachusetts.. Notch Road from North Adams is the steeper of the…
North Berkshire cycling tour - Based at the Maple Terrace Motel in Williamstown, Massachusetts.Rides are 35-50 miles with terrain varying from the flat Ashuwillticook Rail…
Becket MA to Lenox bicycle ride Becket hill climb - A climbing ride in the Berkshires. From Lenox, Massachusetts head east for a few miles on the nice shoulder of Rt.…
Williamstown Natural Bridge bicycle ride Natural Bridge from Williamstown - This 14 mile loop to Natural Bridge from the Maple Terrace Motel in Williamstown Massachusetts starts out with a nice…
Williamstown to Bennington bicycle ride Williamstown – Bennington cycling loop - One of my favorite rides from Williamstown MA heads north across the state line to Bennington Vermont. A good starting…
Ashuwilticook Trail and back Adams MA Ashuwillticook Hill Climb - This ride heads south on the Ashuwillticook Rail Trail from its northern terminus at the Adams Massachusetts visitors center, and heads…
Sandy Brook bicycle ride Sandy Brook Ride - Pete Salomone suggested this as one of the best cycling loops in northwestern Connecticut. The ride originates in Pleasant Valley…
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…
Sandisfield-Stockbridge bicycle ride Sandisfield – Stockbridge Ride - Description from CTBikeRoutes: This rolling to hilly ride showcases some of the best of southern New England scenery: woods, a…
Deerfield River North Adams bicycle ride Williamstown Deerfield River Ride - Anyone who has taken Rt. 2 from North Adams to Greenfield knows that the Mohawk Trail is the most beautiful…
Great Barrington-Stockbridge bicycle ride Great Barrington-Stockbridge Ride - Alford, Stockbridge and West Stockbridge from Great Barrington, Massachusetts This ride starts on Rt. 23 at the Great Barrington –…
Egremont bicycle ride North Egremont Ride - This ride begins at the Windflower Inn on Rt. 23 near the Great Barrington / South Egremont town line. We…
Tyringham-Great Barrington ride Tyringham bicycle loop - This scenic ride with 35-50 mile options starts from downtown Great Barrington Massachusetts and heads out of town up “Three…
Twin Lakes bicycle ride, Berkshires - This ride heads south from the Windflower Inn on Rt. 23 near Great Barrington MA on a nice flat road…
Berkshire Byways two state ride - Description from CTBikeRoutes:  This is a very scenic ride through the beautiful countryside of the Southern Berkshires, passing by farmlands…
Lenox to North Adams 2012 Mass Bike Pike Tour - The 2012 Mass Bike Pike Tour is a four day loop, starting in Great Barrington, heading through New York State…

Pioneer Valley

Food for Justice bike ride Food Justice Bike Ride, Greenfield MA, June 24, 2018 - A newly created charity bike ride called “Food Justice Bike Ride” on June 24, 2018. Start/Finish at Just Roots Community…
Appalachian Mountain Club AMC bicycle repair and Information workshop, Florence MA, Saturday, May 5, 2018 - Want to learn more about how bicycles work, how to maintain them, and how to make basic repairs to them?…
River Valley Ice Cream Ride River Valley Ice Cream Ride, July 28, 2018 - Ice Cream Ride:  http://www.icecreamride.com Start location: Turners Falls, MA Charities: MassBike Pioneer Valley, Turners Falls Riverculture and Community Involved in Sustaining…
Pain in the Mass bicycle ride Pain in the Mass, Amherst MA August 11, 2018 - THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy.…
Death Ride Tour - War on ALS The Death Ride Tour/ Fall Blaze expands the popular Colorado Death Ride tour series to New England.…
Deerfield Bicycle Tour, June 24 – 29, 2018; August 12 – 17, 2018 - Discover Historic Deerfield and the beautiful Connecticut River Valley from the seat of your bicycle this summer! Historic Deerfield presents…
Farm Ride Amherst MA Amherst Pioneer Valley Farm Ride, August 10-13, 2018 - The annual Farm Ride starts from the University of Massachusetts in Amherst, MA and offers two full days of cycling…
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…
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…
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…
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…
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…
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.…
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 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,…
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…
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…
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…
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…
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.…
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…
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.…
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…
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)…
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…
Great River Ride - Starting from Westfield near the Mass Turnpike in western Massachusetts, the Great River Ride is “one of the best century…

Central Massachusetts

Sudbury Century bicycle ride Sudbury NVP Fall Century 2011 - Shown below is the 100 mile route for the Neshoba Valley Pedalers 2011 Fall Century 27 mile http://ridewithgps.com/routes/570108 50 mile…
Wachusett Clinton bicycle ride Wachusett Aqueduct trail - The 9 mile Wachusett Aqueduct extends from the Wachusett Reservoir in Clinton Massachusetts to the John J. Carroll Water Treatment…
Uxbridge Chasm bicycle ride Uxbridge-Chasm State Reservation loop - Known as the Purgatory Ride, this Charles River Wheelmen cycling loop goes through North Uxbridge, Sutton, and neighboring towns. It…
Dudley-Woodstock bicycle ride Dudley – Woodstock Loop - A Seven Hills Wheelmen Ride from Dudley MA Start: Dudley District Court, Lyons Rd., Dudley MA View this ride at http://ridewithgps.com/routes/865365…
Boylston Tower Hill bike ride Tower Hill Ride - Tower Hill bicycle ride
Holden MA bicycle ride Ride for a Reason, Holden MA - Ride For A Reason Bike-A-Thon To benefit the Interfaith Hospitality Network of Greater Worcester, 15-mile, 30-mile and this year we’re…
Quabbin Reservoir ride Quabbin Reservoir ride - The King’s Tour of the Quabbin is a Seven Hills Wheelmen annual century ride around Quabbin Reservoir in western Massachusetts,…
Paxton bicycle ride Paxton Around the Mountain - Around the Mountain is a 53 mile Seven Hills Wheelmen ride from Paxton MA, (53 miles), starting at the Paxton…
Whittinsville bicycle ride Whitinsville Major Taylor Ride - Marshall Walter “Major” Taylor known as “Major Taylor won the world 1 mile track cycling championship in 1899, and was…
Wachusett bicycle climb Climb to the Clouds, Mount Wachusett, Princeton MA: July 16, 2017 - 2012 Description This is a classic Charles River Wheelmen tour, beginning at Nashoba Regional High School in Bolton, MA.(map to…
Bruce Freeman trail 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,…
Rutland-Warren bicycle ride Rutland MA-Warren 50 mile ride - This is a 50 mile Seven Hills Wheelmen Ride, beginning at the Long Pond boat ramp, Routes122 & 122A, in…
Natick-Norfolk bicycle ride Natick-Norfolk ride - Start: Bakery on the Common, Natick MA Description:  This Charles River Wheelmen ride heads south to Norfolk. Route at RideWithGPS View and…
Dover Moose Hill Madness - A CRW Ride Start: Chickering Fields, 114 Dedham Street, Dover MA. Description:  This ride which starts in Dover, heads south…
Framingham Hills to Hopeful - A Charles River Wheelmen Ride Start: George P. King School and Framingham Public Schools Administration Building, 454 Water St., Framingham MA…
Cordaville MA Four Town Ride - This is the Four Burro Charles River Wheelmen bicycle ride Start: George Mooney park, Cordaville, MA. (map to start) Description:…

North Shore

Coast to the Cure Ipswich bicycle ride Coast to the Cure, Gloucester MA September 8, 2018 - Coast to the Cure is an annual fundraising ride for neurofibromatosis. Cycle along flat to rolling hills through Boston’s North Shore.…
Topsfield Road, Ipswich - On Topsfield Road in Ipswich, many of the storm drains have sunken several inches, and the pavement at the edges is crumbling. The road has been the scene of several serious cycling accidents.
Tour de Greenbelt, Saturday, September 29, 2018 - The 2016 Tour de Greenbelt started at the Essex County Greenbelt’s Cox Reservation and Headquarters, 82 Eastern Avenue, Essex, MA…
NSC Blazing Saddles Century, Byfield MA: Saturday, August 18, 2018 - North Shore Cyclists’ Blazing Saddles Century travels through the rural towns of the North Shore and southern New Hampshire past beautiful rivers,…
Topsfield MA North Shore bicycle ride North Shore Tour de Cure, Topsfield MA: Sunday, May 20, 2018 - The Tour de Cure is a series of fundraising cycling events held in 44 states nationwide to benefit the American…
Danvers a Reason to Ride A Reason to Ride, Danvers MA: September 9, 2018 - A Reason to Ride is a fundraiser to benefit cancer research at Beth Israel Deaconess Medical Center, starting from Danvers MA and visiting…
Cycle for Shelter Haverhill bicycle ride Cycle for Shelter, Haverhill MA: July 22, 2018 - The  annual Cycle for Shelter to benefit Emmaus will be held at Northern Essex Community College.   Cyclists can ride a…
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…
A Hole in the Wind, A Climage Scientist’s Bicycle Journey Across the US - Author Talk & Book Signing, Saturday, Sept. 30, 3pm, EBSCO Hall, 5 Peatfield St., Ipswich MA. An epic bicycle journey…
Willowdale Mountain Bike Ride - Willowdale Mountain Bike Ride Willowdale State Forest, Topsfield/Ipswich MA Date: 19 Nov 2016 9:00 AM EST Join the Essex County…
Reid's ride Lynnfield to Gloucester Reid’s Ride, Gloucester MA: July 16th, 2017 - Reid’s Ride is a 28-mile bike ride from Lynnfield High School to Gloucester’s Stage Fort Park to benefit the Reid Sacco…
Ipswich Topsfield and Boxford bicycle ride Ipswich-Topsfield-Boxford - Ride from Ipswich MA to Topsfield, a charming New England village.  A private driveway is used to connect Pineswamp and…
Hamilton Get Off My Road bicycle ride Hamilton MA “Hey you, get off my road!” - Start: Hamilton-Wenham Regional School, 775 Bay Rd, 01982 South Hamilton , MA See map: Google Maps Routes Miles Elevation (ft) Print Download 30…
Castle Neck hike Ipswich Around Castle Neck - This 5.5 mile walk begins on the Green trail from the far right side of the Crane Beach parking lot…
Cape Ann bicycle ride North Shore cycling tour - This cycling tour of the Massachusetts North Shore was developed for Road Scholar, and is based in Ipswich and Newburyport,…
Ipswich MA hilly bicycle ride Hills of Ipswich - There’s about 2300′ of climbing on this 44-mile ride, with a lot of “out and back” on beautiful roads you may…
Danvers MA Topsfield Georgetown bicycle ride Danvers with hills - Thanks to Jason Bartlett for this ride: “There’s an unfortunate scarcity in really hilly routes on the Massachusetts North Shore.…
Haverhill bicycle ride Haverhill riding north - Start: Northern Essex Community College 100 Elliott Street, Haverhill, MA (View map) Meet in the Technology center Parking Lot. Description:…
Salem - Marblehead bicycle ride Salem-Marblehead ride - Start Location: Salem Willows Park at the corner of Fort Ave. and Bay View Ave. near “Salem Willows Park” signage…
Exeter Great Bay bicycle ride Exeter to Great Bay - What to expect: The rides go through the scenic farm country of southern New Hampshire. The terrain is rolling hills…
Topsfield to Merrimack River bicycle ride NSC Saturday ride, Boxford - Start: Masconomet Regional High School, Boxford MA map to start. Directions: From Route 95 take exit 51 (Endicott St) east towards…
Hamilton to Newburyport MA bicycle ride NSC Hamilton to Newburyport - Start: Cutler Elementary School, Asbury St., South Hamilton, MA map to start Description: Enjoy some of the nicest cycling in…
Tyngsborough Pepperell Hollis bicycle ride Tyngsborough Pepper and Maple - Start: Tyngsborough Elementary School, 205 Westford Rd, Tyngsborough, MA (map). Arrow Shape: White T. Description: The ride is remarkable for staying on so…
Ballardvale Andover bicycle ride NSC Over Hill and Dale from Ballardvale - Start locations: Ballardvale MBTA Station, Andover is the traditional start. map to start ($4 parking charge is enforced. There is…
North Reading MA bicycle ride NSC North Reading pigs, ponds and potholes - A North Shore Cyclists ride Start: Ipswich River Park, North Reading map to start Description: Serene back roads, farm stands,…
Topsfield Ipswich North Andover bicycle ride NSC pothole inspection tour, Topsfield - Start: Topsfield Plaza, Main Street, Topsfield, MA. map to start Directions: From Rte 95 N, take Exit 50 to Route 1…
North Shore Cyclists Wakefield bicycle ride NSC Wakefield Thursday ride - Start: Quannapowitt Parkway, northern end of Lake Quannapowitt in Wakefield MA, the end nearest the Rt. 128 interchange. Directions: Rte…
Bradley Palmer State Park bicycle ride NSC Bradley Palmer winter ride - Start location: Bradley Palmer State Park parking lot, Asbury Street, Topsfield MA. From the Asbury Street entrance, take the first…
North Reading MA bicycle ride NSC North Reading evening rides - Start Location: Edith A. O’Leary Senior Center, 50 Bow St., N. Reading MA map to start. The building is at…
Bradford MA to Boxford MA bicycle ride NSC Haverhill-Bradford Tuesday evening rides - Start: Bradford Christian Academy, 97 Oxford Avenue, Haverhill, MA. Map to Start. Oxford Ave and the brick school building is across Rte.…
Ipswich Old Stone Walls bicycle ride NSC Old Stone Walls Ride Ipswich - Start: Ipswich, 16 Hammatt Street parking lot, behind Market Street and Central Street.  map to start 2015 Alternative Start: Cutler…
NSC Portsmouth ride NSC Portsmouth to Maine Seacoast ride - Start: Parrott Ave. Parking Lot, Portsmouth, NH. MAP TO START Directions: From I-95 N, take Exit 3 To Portsmouth. In 1.2…
NSC Halloween Ride NSC Hamilton-Salem Halloween Ride - Description: This ride starts in Hamilton and winds into downtown Salem where there will be large crowds of revelers. Fancy costumes…
NSC Quiet Roads North of Boston NSC Quiet Roads North of Boston, Reading -  Start: REI, Salem St in Reading.  map to start Directions: Route 128 to Exit 40; go around rotary to Route…
NSC Ride to the Sea from Georgetown NSC Ride to the Sea, Georgetown - Start: Perley School, Georgetown map to start Directions: Take Rt. 95 exit 54 west, then follow Rt. 133 west to…
NSC Salt Marsh Ride, ipswich - Start: Ipswich MA downtown central parking lot on Hammatt St. behind Market Street and Central Street map to start Directions:…
NSC Salt Marsh Ride from Rowley NSC Salt Marsh Ride, Rowley - Location: Pine Grove School, Rt. 1A, Rowley MA Directions: Pine Grove School is on the right when going north on…
NSC Bradford ride NSC Bradford ride - Start: Bradford Elementary School, 118 Montvale Street, Haverhill, MA (map to start) Description: All rides (27 miles), medium(40 miles), and long (61…
NSC Willowdale mountain biking NSC Willowdale mountain biking - Start: Linebrook road in Ipswich MA, across from the Marini farm field on the right hand side parking lot. Coming from…
Newburyport-Amesbury bicycle ride NSC North from Cushing Park, Newburyport - Start: Cushing Park, Kent St., Newburyport, MA. Google Directions and Map to Start Location. This is a North Shore Cyclists ride.…
Arrowed rides on the North Shore Cyclists site - Ride name City and arrow Applecrest Amesbury Back to the Saddles Again Byfield Bagels and a Witch Boxford Best of Ipswich…
Amesbury - Great Bay ride NSC North to Great Bay, Amesbury - Start: Amesbury Elementary School, 20 South Hampton Rd., Amesbury map to start Directions: Rte. 95 to exit 58 for Rte.…
Nashua River Ramble Nashua River Ramble - Start: Tyngsboro Elementary School; 205 Westford Rd, Tyngsboro, MA map to start Directions: Take Exit 34 on Hwy 3. At…
Topsfield ride NSC Topsfield Monday ride - Start: Topsfield Plaza, Topsfield map to start Directions: From Rte 95 N, take Exit 50 to Route 1 North. In…
Minuteman Ride from Lawrence, MA Minuteman Ride from Lawrence, MA - Start: Greater Lawrence Vocational High School 57 River Road, Andover MA map to start Directions: I-93 N, Exit 45 River…
Cheese and Whine bicycle ride from Newburyport MA NSC Cheese and Whine from Amesbury - Start location: Amesbury Elementary School, So. Hampton Rd., Amesbury, MA. Map to Start. From  Rte 95 to exit 58 for…
Merrimack River ride from Newburyport MA NSC Merrimack River ride from Newburyport, MA - Start: Cushing Park, Newburyport MA map to start Directions: From Rte. 95 take exit 57 Rte 113 east. Go for…
Merrimack River from Ipswich MA Merrimack River ride from Ipswich MA - Start Location: Ipswich Middle and Senior High School, 130 High St., Ipswich MA. (we start from the parking lot behind the…
coastal bicycle ride from Newburyport, MA NSC Let’s Go Coastal from Newburyport, MA - Start: Cushing Park, Newburyport map to start Directions: From Route 95, take Exit 57 for Route 113 East. Go for 2 miles and…

Boston area

Boston to Provincetown H2B Harbor to the Bay Harbor to the Bay (H2B), September 15, 2018 - The H2B Ride is a 125 mile ride from Boston to Provincetown to support people living with HIV and AID.…
Bike to the Beach, Boston to Newport: September 1, 2018 - Bike to the Beach is a 501(c)3 non-profit organization creating a community of cyclists, autism advocates, fitness junkies, and beach lovers to…
Brain Tumor bicycle ride Brain Tumor Ride, Boston: May 20, 2018 - Boston Brain Tumor Ride is an event to raise awareness and much-needed resources to fund critical brain tumor-specific programs to…
Bikes Not Bombs route Bikes Not Bombs, Jamaica Plain MA: June 10, 2018 - Bike Not Bombs’ Bike-A-Thon route maps are  online for all four distance options. The rides start in the Jamaica Plain neighborhood of…
Jingle Ride! Arlington to Boston - On Sunday, December 11th, 2016 join the 20th Annual Ciclismo Classico Jingle Ride.  This leisurely and festive singing bike parade goes from Arlington…
Soldier ride 2016, Lexington MA - Soldier Ride is a unique four-day cycling opportunity for wounded service members and veterans to use cycling and the bonds of…
Boston Hub on Wheels, Sep. 17, 2017 - This year, riders  have the option of selecting either the 10-mile family-friendly route or the more challenging  40-mile course. Visit…
Boston to Provincetown bicycle ride 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…
South Harbor Boston bicycle ride South Bay Harbor Trail - The South Bay Harbor Trail is a 3.5 mile-long pedestrian – friendly urban bike trail that will connect Lower Roxbury,…
Newton MA bicycle ride Newton MA fitness ride - This is a Charles River Wheelmen weekly ride from Newton MA, with multiple distance options. Scenic rolling roads through Needham,…
Boston Best Buddies bicycle ride Boston Best Buddies Ride - Best Buddies Challenge Riders choose from three options for distance: 100 miles, 50 miles or 20 miles. No matter what…
Dorchester-Pleasure Bay ride - This short ride starts from the Thomas J. Kane Square and playground park in Dorchester MA , a residential section…
Bourne to Provincetown Cape Cod bicycle ride Cape Cod Getaway: June 24-25, 2017 -  150 miles, Boston Harbor to Provincetown The Cape Cod Getaway is the largest MS ride in New England. On Day…

Southeast Massachusetts

Buzzards Bay Watershed Ride Buzzards Bay Watershed Ride: September 30, 2018 - Celebrate the beauty of the Buzzards Bay region by participating in the Buzzards Bay Watershed Ride! Whether you’re an avid…
Martha's Vineyard ride Vineyard Warrier Triathlon: September 8, 2018 - Vineyard Warrior Triathlon on the Island of Martha’s Vineyard: A 1 mile swim, 24.6 mile bike, and a 6.2 mile…
Cape Cod Canal bikeway Cape Cod Canal Bikeway - The Cape Cod Canal Bikeway is two separate paved paths that connect Buzzards Bay with Scusset Beach on the mainland…
Rhode Island Sound and Buzzards Bay - This Charles River Wheelmen ride begins at Horseneck Beach State Reservation south of Westport MA, with views of Rhode Island…
Dartmouth MA bicycle ride Dartmouth Coastal Metric Century - This Narragansett Bay Wheelmen ride starts at the University of Massachusetts campus in Dartmouth MA and heads southwest through Westport…
Swansea bicycle ride Swansea MA cycling loop - This Narragansett Bay Wheelmen (NBW) loop around Swansea MA crosses briefly into Rhode Island. Start: Swansea II Shopping Center Route…
Seekonk Century bicycle ride NBW Seekonk – Plymouth Cranberry Century - This Narragansett Bay Wheelmen (NBW) ride begins in Seekonk MA near the border with East Providence RI, and loops to…
Boston to Provincetown bike ride Boston to Provincetown - 125-Mile Ride: Boston to Provincetown:  Those riders who want to challenge themselves to ride the full 125 miles will start…
Narragansett Bay Wheelmen NBW bicycle rides Cycling in southeast Massachusetts - Cue sheets for the following  rides are provided by Narragansett Bay Wheelmen Belchertown Central Massachusetts Spectacular Bourne, MA The Cape…
Walpole-Dover bicycle ride Walpole-Dover loop - This nice ride starts downtown in Walpole, Mass and heads out through rural countryside. After 8 miles you pass through…
Wareham-Plymouth bicycle ride Wareham-Manomet Bluffs Ride - NBW Wareham -Manomet Ride (# 153) Start:  Wareham  MA Town Hall  (map to start) Descripton: The ride passes through the…
Swansea-Dighton Rock bicycle ride Swansea-Dighton Rock Ride - NARRAGANSETT BAY WHEELMEN #102 SWANSEA – DIGHTON ROCK RIDE Start:     Swansea Shopping Center, Swansea, MA  (map to start) Descripton: …
Unon CT – Brimfield MA Antiques Ride - This is the Narragansett Bay Wheelmen’s Brimfield Antique Ride, 34 miles from Union Connecticut. Start: Public library or church, downtown…
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…
Bourne to Provincetown Cape Cod bicycle ride Cape Cod Getaway: June 24-25, 2017 -  150 miles, Boston Harbor to Provincetown The Cape Cod Getaway is the largest MS ride in New England. On Day…
Rockland south coastal ride - This Charles River Wheelmen ride is along shady, quiet roads offering great vistas of the Massachusetts shore shore coastline. The…
Raynham MA Cranberry Metric Century Ride - NARRAGANSETT BAY WHEELMEN #81CRANBERRY METRIC 17-35-62 miles Start: Staples Plaza, junction Routes 44 and 24, Raynham, MA Description: Easy ride…

Cape and the Islands

The Last Gasp, Sandwich to Provincetown MA: September 16, 2018 - The Annual LAST GASP!  The 27th Annual LAST GASP! Ride from Sandwich to Provincetown in support of several Cape Cod…
Cycling Martha's Vineyard Ride the Vineyard, Martha’s Vineyard, Saturday, May 5, 2018 - Ride the Vineyard the Multiple Sclerosis fundraiser on Martha’s Vineyard, Massachusetts. With the quaint charm and beautiful ocean views of…
Cape Cod Rail Trails Cape Cod, Old Colony and Nauset bike Trails - The 22-mile Cape Cod Rail Trail follows the former Old Colony Railroad right-of-way from South Dennis to South Wellfleet, passing…
Cape Cod Canal bikeway Cape Cod Canal Bikeway - The Cape Cod Canal Bikeway is two separate paved paths that connect Buzzards Bay with Scusset Beach on the mainland…
Cape Cod Falmouth bicycle ride Inner Cape Cod Metric Century - This ride begins in Bourne at the entrance to Cape Cod, then south to Falmouth, crosses the Cape north to…
Bourne Cape Cod bicycle ride Cape Cod Ride - A Charles River Wheelmen ride Description: Ride on lightly traveled roads with views of Cape Cod Bay, Buzzards Bay, Nantucket…
Bourne-Falmouth bicycle ride 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…
Bourne to Provincetown Cape Cod bicycle ride Cape Cod Getaway: June 24-25, 2017 -  150 miles, Boston Harbor to Provincetown The Cape Cod Getaway is the largest MS ride in New England. On Day…

 More Massachusetts rides

Ride for Food Ride for Food – Women’s Lunch Place; September 23, 2018 - Every mile helps a woman in need. Ride for Women’s Lunch Place Team,  Sunday, September 23, 2018.  Choose from 10, 25…
Tour Opacum bike ride Opacum Tour, Sturbridge MA: July 8, 2018 - Join Opacum Land Trust for this spectacular scenic bike ride through Sturbridge, Brimfield, Brookfield and surrounding towns and take in the…
The Last Gasp, Sandwich to Provincetown MA: September 16, 2018 - The Annual LAST GASP!  The 27th Annual LAST GASP! Ride from Sandwich to Provincetown in support of several Cape Cod…
Autumn Escape Bike Trek, Plymouth MA: September 28-30, 2018 -   Date: September 28-30, 2018 Location: Plymouth, MA Link:  http://action.lung.org/site/TR?fr_id=13912&pg=entry Beneficiary:  American Lung Association http://www.lung.org The American Lung Association Autumn Escape…
Food for Justice bike ride Food Justice Bike Ride, Greenfield MA, June 24, 2018 - A newly created charity bike ride called “Food Justice Bike Ride” on June 24, 2018. Start/Finish at Just Roots Community…
Cycling Martha's Vineyard Ride the Vineyard, Martha’s Vineyard, Saturday, May 5, 2018 - Ride the Vineyard the Multiple Sclerosis fundraiser on Martha’s Vineyard, Massachusetts. With the quaint charm and beautiful ocean views of…
Will Bike 4 Food: Hatfield MA, Sunday, September 30, 2018 - WB4F is a non-competitive ride through the beautiful Pioneer Valley to raise funds for The Food Bank of Western MA.…
Boston to Provincetown H2B Harbor to the Bay Harbor to the Bay (H2B), September 15, 2018 - The H2B Ride is a 125 mile ride from Boston to Provincetown to support people living with HIV and AID.…
Tour de Greenbelt, Saturday, September 29, 2018 - The 2016 Tour de Greenbelt started at the Essex County Greenbelt’s Cox Reservation and Headquarters, 82 Eastern Avenue, Essex, MA…
Holliston Cycle for Life bicycle ride Cycle for Life, Holliston MA: October 6, 2018 - Cystic Fibrosis Cycle for Life  Start:  101 Summer St., Holliston, MA  (map) Description: 12, 30 and 65 mile route options. Metric…
Coastal Trails Newburyport MA 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,…
Buzzards Bay Watershed Ride Buzzards Bay Watershed Ride: September 30, 2018 - Celebrate the beauty of the Buzzards Bay region by participating in the Buzzards Bay Watershed Ride! Whether you’re an avid…
Tour de South Shore, Hingham, MA, September 22, 2018 - The McCourt Foundation’s 2018 Tour de South Shore Athletic Festival offers a 25 and 50 Mile Bike, a 5K Walk…
Berkshires to Boston, September 12-16, 2018 - Berkshires to Boston bicycle tour
Tour de Cure Topsfield MA Tour de Cure New England Classic, Bedford, MA : July 14-15, 2018 - 2 New England Classic 150 & 550 The New England Classic Tour de Cure is a weekend or weeklong adventure…
Martha's Vineyard ride Vineyard Warrier Triathlon: September 8, 2018 - Vineyard Warrior Triathlon on the Island of Martha’s Vineyard: A 1 mile swim, 24.6 mile bike, and a 6.2 mile…
Impact Ride, Attleboro MA: September 29, 2018 - Join some of the best cycling  in southeastern New England with the IMPACT Ride. Proceeds go to the fight against…
River Valley Ice Cream Ride River Valley Ice Cream Ride, July 28, 2018 - Ice Cream Ride:  http://www.icecreamride.com Start location: Turners Falls, MA Charities: MassBike Pioneer Valley, Turners Falls Riverculture and Community Involved in Sustaining…
Brain Tumor bicycle ride Brain Tumor Ride, Boston: May 20, 2018 - Boston Brain Tumor Ride is an event to raise awareness and much-needed resources to fund critical brain tumor-specific programs to…
NSC Blazing Saddles Century, Byfield MA: Saturday, August 18, 2018 - North Shore Cyclists’ Blazing Saddles Century travels through the rural towns of the North Shore and southern New Hampshire past beautiful rivers,…
Bikes Not Bombs route Bikes Not Bombs, Jamaica Plain MA: June 10, 2018 - 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-Stamford tri-state bicycle ride Tri-State Trek, MA-RI-CT: June 22, 2018 - Tri-State Trek, Riding for a cure for ALS, Chestnut Hill MA to West Haven, CT Day 1 route Day 2…
Wayland ALS bicycle ride Ride to defeat ALS, Wayland MA, September 23, 2018 - Ride to Defeat ALS is a community fundraising event that creates the hope and action needed to conquer Lou Gehrig’s…
Topsfield MA North Shore bicycle ride North Shore Tour de Cure, Topsfield MA: Sunday, May 20, 2018 - The Tour de Cure is a series of fundraising cycling events held in 44 states nationwide to benefit the American…
Pain in the Mass bicycle ride Pain in the Mass, Amherst MA August 11, 2018 - THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy.…
Rodman Ride for Kids Rodman Ride for Kids, September 22, 2018 - The Rodman Ride for Kids is a 25, 50, and 100-mile non-competitive cycling fundraiser for at-risk children in Massachusetts and…
Positive Spin for ALS Positive Spin for ALS, September 23, 2018 - The ALS Association Massachusetts Chapter hosts its Annual “Positive Spin for ALS” cycling event at the Longfellow Club, located at…
Cycle Massachusetts State Bike Tour, Aurust 4-10, 2018 - Cycle Massachusetts is dedicated to Celebrating Cycling in Massachusetts. We organize, participate and support many other rides in Massachusetts and…
Danvers a Reason to Ride A Reason to Ride, Danvers MA: September 9, 2018 - A Reason to Ride is a fundraiser to benefit cancer research at Beth Israel Deaconess Medical Center, starting from Danvers MA and visiting…
Cycle for Shelter Haverhill bicycle ride Cycle for Shelter, Haverhill MA: July 22, 2018 - The  annual Cycle for Shelter to benefit Emmaus will be held at Northern Essex Community College.   Cyclists can ride a…
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…
Cycle Massachusetts Cycle Massachusetts State Bike Tour – August 4 – 10, 2018 - Cycle Massachusetts State Bike Tour 2018 All our proceeds go to Massbike and we are their number one donor each year – check…
Nantucket bike rides - Deb and I celebrated her late April birthday with a trip to Nantucket, taking advantage of great early season rates at…
Death Ride Tour - War on ALS The Death Ride Tour/ Fall Blaze expands the popular Colorado Death Ride tour series to New England.…
Deerfield Bicycle Tour, June 24 – 29, 2018; August 12 – 17, 2018 - Discover Historic Deerfield and the beautiful Connecticut River Valley from the seat of your bicycle this summer! Historic Deerfield presents…
Willowdale Mountain Bike Ride - Willowdale Mountain Bike Ride Willowdale State Forest, Topsfield/Ipswich MA Date: 19 Nov 2016 9:00 AM EST Join the Essex County…
Massachusetts Formidable Ride - The Formidable Challenge is the toughest road ride in Massachusetts. The 2016 Formidable offers three routes, a 160-mile pavé ride, a century version,…
Soldier ride 2016, Lexington MA - Soldier Ride is a unique four-day cycling opportunity for wounded service members and veterans to use cycling and the bonds of…
Hingham Fall Foliage Ride Against Hunger - Fall Foliage Ride Against Hunger, Hingham, MA, Sat Oct 22, 2016. Enjoy a scenic ride through Hingham and Cohasset past…
Ride to Thrive, Harvard MA, October 14, 2018 - Begin your ride at the Healing Garden in Harvard MA & choose your route in support of the Healing Garden’s…
Where’s Chester? - A North Shore Cyclists ride from Amesbury MA to Chester NH on mostly wooded roads past farms and through quaint historic towns. The short route…
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…
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…
Boston Hub on Wheels, Sep. 17, 2017 - This year, riders  have the option of selecting either the 10-mile family-friendly route or the more challenging  40-mile course. Visit…
Western New England Greenway - The Western New England Greenway is part of U.S. BICYCLE ROUTE 7 that connects New York to Montreal. The corridor largely follows near U.S.…
Reid's ride Lynnfield to Gloucester Reid’s Ride, Gloucester MA: July 16th, 2017 - Reid’s Ride is a 28-mile bike ride from Lynnfield High School to Gloucester’s Stage Fort Park to benefit the Reid Sacco…
Farm Ride Amherst MA Amherst Pioneer Valley Farm Ride, August 10-13, 2018 - The annual Farm Ride starts from the University of Massachusetts in Amherst, MA and offers two full days of cycling…
Bravehearts ride, Harvard MA Bravehearts Ride, Harvard MA: JULY 14, 2018 - The National Brain Tumor Society Bravehearts Ride offers a 50-mile, 25-mile, and 2-mile children’s route. Proceeds benefit the National Brain Tumor…
Bicycle rides in Massachusetts -  Berkshires Pioneer Valley Central Massachusetts North Shore Boston area Southeast Massachusetts Cape and the Islands  More Massachusetts rides
Lexington MA metric century Massachusetts-New Hampshire 200K - This route is provided by New England Randonneurs, starting from Lexington, MA Route at RideWithGPS View and print cue sheet…

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