Five Spectacular Biking Trails in Greater Boston

From a revolutionary 10-mile ride to a 2.6-mile Deer Island loop, we’ve rounded up some of the region’s best.

Illustration by Jeannie Phan

1. Minuteman Bikeway

Beginning in the charming town of Bedford and ending in the bustling heart of Cambridge, the 10-mile Minuteman Bikeway retraces the footsteps of Revolutionary War heroes. As you pedal along the smooth asphalt of the rail trail, take in historic points of interest such as the Lexington Battle Green and the destination of Paul Revere’s midnight ride—and be sure to stop off at Rancatore’s Ice Cream in Lexington for a cool treat along the route.

2. Deer Island

Looking for a true escape just outside the city limits? Located just off the coast of Winthrop, this “island” with 60 acres of open space is actually a peninsula featuring a 2.6-mile loop trail. From the route, you can take in gorgeous views of the Boston skyline, the Harbor Islands, and the Atlantic Ocean (plus the area’s waste-water treatment plant, if you’re into that sort of thing). Short and sweet, the laid-back pathway is perfect for a leisurely weekend morning.

3. Emerald Necklace

When one urban park isn’t enough, hop on this 7-plus-mile gem, which connects Boston Common to Franklin Park as it passes through an interconnected series of lush green spaces designed by Frederick Law Olmsted, the father of American landscape architecture. The path varies from paved to packed gravel, so be prepared for some off-road adventure as you peep the gardens, ponds, and wildlife along the way.

The Charles River bike lane. / Photo by Eduardo Fonseca Arraes via Getty Images

See also: The Best Bike Paths in Boston

4. Charles River Bike Path

Visitors and locals alike love this 23-mile loop, which hugs the banks of the Charles from Boston all the way to Waltham, for its unparalleled views of the cityscape on both sides of the river—so be sure to put it on the itinerary when you have out-of-town guests who like to bike. Even better: The path is mostly flat, paved, and well-maintained, making it perfect for cyclists of all skill levels.

5. Neponset River Greenway Trail

Just a hop, skip, and a wheelie from downtown is this 8.2-mile paved trail, which runs along the Boston and Milton shoreline of the Neponset River—a “harvest river” once used as part of the fur-trading route in the 1600s. This is a rail trail, but it does have some trickier sections along the Truman Parkway, so less-experienced riders should start at Tenean Beach or Mattapan Station. You’ll be rewarded with views of tree-lined valleys, river marshes, the first chocolate factory in America, and maybe even some fishermen.

First published in the print edition of the June 2023 issue with the headline “Pedal Power.” See also: The 10 Best Bike Paths in Boston.