Amazing Outdoor Workouts: Bike

No matter your skill or experience level, there’s a ride in Boston for you. Just mount up, pedal safely, and let our experts guide you.

By Casey Lyons | Boston Magazine |

The HarborWalk offers fine views for cyclists. (Photo by James Michelfelder and Therese Sommerseth.)

Three of the city’s most dedicated bicyclists dish on the trails, routes, and paths that keep them coming back for more.

South Boston, HarborWalk
Nicole Freedman, Former Boston Bike Czar

The slice of the HarborWalk from the federal courthouse in Southie to UMass Boston in Dorchester offers mostly off-street cycling and what Freedman calls “one of the best views in Boston.” Head south from the courthouse on this flat path (9 miles each way), passing the L and M Street beaches and Carson Beach, and take a restroom and hydration break at the Edward J. McCormack Bathhouse. Continue on to the JFK Library (there’s a very short dirt section just before it), then follow the coast past weekend fishermen to Morrissey Boulevard. Keep in mind that the paths can be busy with strollers, runners, and beachgoers in the summertime.

Needham/Sherborn, Route 16 South
Billy Starr, Pan-Mass Challenge Founder and Executive Director

If you like your pavement as smooth as your Lycra, head out toward Needham and work your way south – southwest for as long as you want to go. This area allows you to exchange the crowds on the Minuteman Bikeway for tree-lined streets that weave through the countryside. But Starr won’t recommend a particular route. “Why not get lost? That’s the whole point,” he says. “I won’t define a route for you. I dare you to take a leap and think outside the box.” Of course, you probably will still want a guide of some sort. Starr recommends the Rubel Maps, available at good bike shops and at

Middlesex Fells, Mountain Bike Loop
David Watson, MassBike Executive Director

Just 8 miles north of the city (and accessible by commuter rail and the Red Line), Middlesex Fells offers enough fire roads, forest roads, and single track to keep bikers busy for hours. For the best outing, Watson recommends circling the North, Middle, and South reservoirs on the 6.3-mile Mountain Bike Loop. (Note to beginners: “Fells” translates from Saxon as “rocky, hilly, place.” Be prepared to dismount and walk in a few steep sections.) The reward is worth it. “You’re on a narrow trail up on a hillside overlooking the Winchester reservoirs through the trees, and you can see the light sparkle off the water,” Watson says. “For me, that’s kind of my Zen place.”