Boston Road Rides & Routes

The Minuteman Bikeway – 19 miles

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The Minuteman Bikeway was built by the Commonwealth of Massachusetts along the route of a former railway. Used by local residents and visitors from near and far, it’s totally car free!

Bike to the Sea – 18 miles

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The Bike to the Sea follows the Strand Community path, a part of the East Coast Greenway. Beginning on the banks of the Mystic River, it’s a wonderful way to experience the North Shore of Massachusetts.

The Paul Revere Ride to Freedom – 22 miles

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This ride mimics the legendary one that Paul Revere took on the night of April 18th, 1775 to warn the militia in Lexington of the British advancements.

This route ends at the Concord train station for a speedy return to the city. Check here for more information on the commuter rail.

Dover Loop – 35 miles

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The Dover Loop is a favorite of many amateur and pro racers in Boston. The rolling hills make for an excellent workout!

The South Bay Harbor Cruise – 25 Miles

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This ride is based on a tour that Jessica Mink (who runs made for a special event that we guided and is designed to show off the bike ability of Boston’s outer neighborhoods, as well as the gaps in the proposed/partially constructed South Bay Harbor Trail network.

Great Farms Ride – 60 Miles


Get out of the city and explore the rolling hills and farms of Concord and Carlisle. We also strongly recommend making a stop for Ice Cream at Kimball Farm!

Three Islands Ride – 70 Miles

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Fill your lungs with the sea breeze on this ride to Salem and back – with breathtaking views of the ocean from Deer Island, Nahant, and Marblehead, this ride is a sure-fire day trip in the summer or fall.

Provincetown – 123 Miles

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Provincetown is the last town on the eastern end of Cape Cod. Known around the USA as a haven for LGBTQ people, the town has a very open and carefree atmosphere, plenty of beaches, great nightlife, and fantastic seafood.