D2R2 has a more popular meaning but I like to think of it as Dry Dirt Road Riding. Such roads are perfect for the vintage (or vintage-like) all-road cycle. No need for those knobbly tires, just ones that are slightly wider and still work great on pavement. You can even take a three-speed on most. Furthermore, one can ride out to such roads easily on an all-road bike, without having to drive.

For a few years, I’ve been trying to create a map of the dirt roads in the Greater Boston Area. This is fun cycling and I don’t see a need to keep these great roads a secret. But more so, we could use the help finding more great roads that are nearby and good for all-road bikes.

Here is my map centered on Concord & Lincoln. Pan around, there are other great roads on the North and South Shores.

View East Mass Dirt Roads in a larger map

Of course, D2R2 is more than just riding on dirt roads now that mud season has ended (not that we have much of a mud season in Boston 🙂 The real D2R2, that is Deerfield Dirt Road Randonee, is only about six weeks away; and registration is still open… Which means it is time to get some preparation rides in.

I just put together a map of a few D2R2 preparation routes in the Boston Area. Over the years I’ve ridden on each to varying degrees and I plan to ride on them more in the next few weeks to get ready. The map is intended to be displayed with ‘East Mass Dirt Road’ map posted above, so you can see what is dirt and what isn’t.

View D2R2 Preparation Routes in a larger map

I have mapped three routes. The two just west of Boston are the routes that I typically ride, and I suspect most here will understand the best. The Prospect Hill Loop is one of the best hill climbs in the area. The BCC Loop is nice specifically because of the large quantity of unpaved roads, though pedestrians will likely slow you down.

The Plymouth Loop is one I did a few years ago. The dirt roads here are nice, but can be rough, and thus good practice for D2R2. You can even take the commuter rail down. Just make sure you don’t miss the train back, but if you do there is a fancy pizza joint nearby.

I’ve ridden on a North Shore loop, which is almost a century. It didn’t have as much unpaved roads, but it is a very nice place to ride. There were a couple fords and a few of the old roads are a good challenge. Once I find the cue sheet, I’ll add it to the map.

If you have another route or other dirt road suggestions, let us know and I’ll update the maps.

Lastly, if you’re looking for others to ride these roads with, post a comment, I’m sure others (including myself) would enjoy your company on our next ride.

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