Cochituate Rail Trail, in Felchville

Ride a Rail-to-Trail New England Towns Tour

Photo: John Phelan

Connect a pair of protected rail-to-trail pathways for a classic town-and-country cycling loop just outside of Boston.

If you’re looking for a worthy bike ride near Boston, you don’t need to head farther than the beautiful towns just west of downtown. Extend out of the city center and you’ll find scenic miles on protected bike paths—not only picturesque views and pleasant riding, but opportunities to log some distance without riding beside cars. 

Prior to reaching Framingham, you can gain access to many miles of purpose-built bike path separated off main roads through wooded areas. Combining some of these standout protected corridors (with light transit through local communities) yields plenty of options for linking together memorable rides. Here’s one classic New England town-and-country route to get you accustomed to the area and its offerings, which cater to many seasons and to all ability levels—great for a solo after-work ride or a relaxing tour with the whole family.

A bike is seen near wayland 88 miles to northampton 16 miles to boston

Recommend Route

This mostly paved 21-mile loop starts in the town of Wayland, Mass., and has less than 1,000 feet of elevation gain. A gravel bike works well, as does a road bike, so long as you don’t have racing tires, even in the brief chip-stone sections. Look for parking downtown at the trail access parking lot near the Wayland Free Public Library, which also has a public bathroom open most days. From the parking lot, hop onto the protected Mass Central Rail Trail and start biking east. (The MCRT is a more than 100-mile-long trail created over a decommissioned rail line that stretches east to west across Massachusetts from Boston to Northampton.) 

Ride about 3 miles on the paved path before you reach Weston. Here, bike off the trail and into the town of Weston along the road. Head south past the Weston Town Hall and continue down School Road past the Weston Public Library until you reach its intersection with Wellesley Street. Ride about a mile and a half before taking a right on to South Avenue. Ride a half-mile before taking a left on Winter Street. 

After just shy of 2 miles, take another left onto Rathbun Road and bike until the road ends at the intersection with Oak Street in Natick. (You’ll be just over halfway done when you reach Natick.) There, take a left onto Oak Street and follow it until it ends at the intersection of Bacon Street (just a name, unfortunately, you’ll have to bring your own mid-ride bacon). 

Hop on the paved, shared-use Cochituate Rail Trail pathway and head north out of Nantick (see updates on this other rail-to-trail pathway here). Follow the trail until it ends and continue north on Concord Street, which turns into Elm Street and then Landham Road. Two miles after leaving the Cochituate Rail Trail pathway, take a right onto Pelham Island Road and ride about 3 miles back into Wayland to finish your ride.

Shorter Option

Rather than doing this loop, complete an out-and-back ride along the Mass Central Rail Trail. Start in Wayland and ride either east or west along the path before turning around and heading back to the parking lot. 

Refresh & Refuel

Pull off the road or path in any one of the passing towns to stop at a shop or gas station to load up on water and snacks. For a quick bite before or after your ride, consider The Bagel Table near the MCRT access just west of Wayland, along this historic rail trail

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.