Category: Massachusetts

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 […]

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 […]

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 great swamp and then the sleepy village of Tyringham. After passing through this classic hamlet there are vistas of the surrounding Berkshires on your way to the well-known […]

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.  View the 93 mile version of this ride: Route at RideWithGPS View […]

Northampton Bike Fest

Northampton BikeFest

Routes provided by the Northampton Cycling Club, Northampton, MA Century Ride A challenging 104 mile loop through some of the best scenery of western Massachusetts and southern Vermont. Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course 72-Mile Ride A metric century […]

Concord bicycle ride

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 […]

Acton Century bicycle 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 […]

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 – 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 […]

Stow MA bicycle ride

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. […]

Wayland - Concord ride

Wayland-Concord-Boxborough loop

This Charles River Wheelmen ride is known as “A River Runs Through It” and takes you through beautiful rolling wooded countryside west of Boston, with views of the Sudbury and Assabet River plains. All rides pass through Concord, Sudbury, Wayland, and Lincoln, and the 48-mile ride includes Stow […]

Weston - Concord ride

Weston-Concord loop

A Charles River Wheelmen Ride Description: The short ride travels through Weston, Wayland, Sudbury, Concord and Lincoln; the long ride adds Acton and Carlisle. The lunch stop is in Concord center. The terrain is rolling. Start: Weston High School, 444 Wellesley Street, Weston. (map) Cuesheets: Long, Short Route […]

Bedford - Harvard ride

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 […]

Maynard - Harvard ride

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. Description Both short and long rides include several hill climbs and smooth descents in the Harvard/Bolton “big thigh” country. The […]