Spectacular Places to Go Cycling in Massachussetts

Cyclist | Morning ride | © Ed Dunens/Flickr
Dave Afshar

From quiet oceanside bike paths to steep mountain trails to urban expeditions, the bay state has plenty to offer hardcore cyclists and casual bike riders alike. We take a look at the best ways to have fun on two wheels in Massachusetts.

Cape Cod

The quintessential New England weekend getaway boasts gorgeous coastal views, quaint villages, and cheap campsites, all of which are accessible by bike. From Boston, take the CapeFlyer train from South Station to Hyannis and start your adventure from there.

Cape Cod

Cape Ann

Accessible from Boston via the commuter rail, Cape Ann is a perfect option for anyone in need of a day trip out of the city. The area isn’t too hilly and the views of the rocky coastline, old houses, and seafood shacks deliver an authentic New England experience, all in a day.

South Shore

At roughly 35 miles long, the South Shore bike path is great for intermediate cyclists seeking a day trip that’s challenging yet not overwhelming. Check out the Blue Hills Reservation and the Cohasset-Scituate coast for some of the most scenic bike paths in all of Greater Boston.

The Berkshires

Located in rural western Massachusetts, this mountainous region is famous for its foliage, farm-to-table food culture and outdoor activities. For those looking to take on a challenge, the Berkshires to Boston Bicycle Tour is a four-day, 240-mile expedition across the entire state.

Scenic Berkshire Road

Harold Parker State Forest

This massive campground features both mountain biking and on-road bike paths, as well as a playground and swimming pond, making it an ideal choice for families and kids.

Fresh Pond Reservation

Conveniently located in Cambridge, the Fresh Pond Park bicycle path is great for Boston residents in need of a quick escape from the hustle and bustle of downtown. Although the loop bike path is only three miles long, it is child and dog-friendly, and offers a safe and easy trip for casual riders.

Willowdale Forest

Located in Topsfield, roughly an hour’s drive north of Boston, Willowdale Forest offers mountain bikers a scenic off-road trek that can be completed in a day. The trails are well-groomed, easily accessible, and open to the public from sunrise to sunset.


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