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Boston Road Rides & Routes

Weekly Shop Ride – 20 miles


Back from the days when we ran our weekly shop ride, this was our route of choice! Great for folks who don’t mind some urban riding, and are looking for a shorter ride. Excellent choice for an evening workout!

The Minuteman Bikeway – 39 miles


This out-and-back ride follows the Minuteman Bikeway, one of the nation’s most popular rail trails. Follow this route for a (nearly) car-free ride to the suburbs and back.

Please note the Minuteman Bikeway is a family-friendly environment. Those looking for a fast-paced road ride may prefer following our other routes.

Walden Pond – 47 miles


This shorter loop uses the Minuteman Commuter Bikeway to navigate in and out of the city. The route also passes Walden Pond, the famous site of Henry David Thoreau’s 19th century cabin. Walden Pond is also a great place to get off the bike and go for a swim!

Recommenced for those looking for an easier ride, or for those looking to cool off on a hot summer day. Please note that the Minuteman Bikeway is a family-friendly environment and is not recommended for high-speed road riding.

Dover Loop – 44 miles


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

Cross Bike Loop – 54 Miles


Renting one of our cyclocross bikes? This is a perfect route to get you on some mixed terrain. While this route is not overly-technical, it will get you off the pavement and is not recommended for road bikes!

Great Brook Farm – 60 Miles


Our most popular route!

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 Great Brook Farm!

Wachusett Mountain – 119 Miles


Starting at sea level, this century-ride follows winding country roads west to Wachusett Mountain. You can see Boston from the 2000′ summit!

Provincetown – 123 Miles


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. This one-way ride is a great way to see a lot of Eastern Massachusetts. Consider taking the ferry back directly to our shop!

Paul Revere Ride to Freedom Bike Tour - 47.5 Miles


Enjoy this 45.8-mile loop trail near Boston, Massachusetts. Generally considered a moderately challenging route, it takes an average of 14 h 19 min to complete. This is a popular trail for road biking, running, and walking, but you can still enjoy some solitude during quieter times of day. The best times to visit this trail are April through September. Dogs are welcome, but must be on a leash.



More Resources

Road Biking Resource Guide

Stop by our shop and grab a free copy of this guide!

Cycle to the Source Route Map and Cue Sheet

Ride With GPS routes by Charles River Wheelers

MIT Cycling Club Routes