Road Rides

Looking to get outside the city and put some miles in? Look no further! Here are some longer routes to get your heart rate up and satisfy your skinny-tired fantasies:
Shorter rides at the top, longer ones at the bottom. Have a favorite route you’d like to share? Let us know! Sent an email to, and we’ll be happy to put it up here.
Using a GPS device? You can download KML files from Google maps, and use your device’s software to convert them to a proper file format. We’ve mapped some of these rides using our Garmin Edge, so stay tuned for more of those to come!

The Paul Revere Ride to Freedom – 22 miles (each way)

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.

View Paul Revere Ride to Freedom in a larger map
This route is also available for download through:


The South Bay Harbor Cruise – 25 Miles

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 bikeability of Boston’s outer neighborhoods, as well as the gaps in the proposed/partially constructed South Bay Harbor Trail network.

View The South Bay Harbor Cruise in a larger map

Dover Loop – 47 miles

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

View Dover Loop in a larger map

Three Islands Ride – 70 miles

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.

View Three Islands Ride in a larger map