Boston Road Rides & Routes

Weekly Shop Ride – 20 miles

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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

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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.

Dover Loop – 44 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!

Walden Pond – 46 miles

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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 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.

Cross Bike Loop – 54 Miles

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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 – 58 Miles

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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

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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

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

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