I continue to be amazed at how many great roads there are for cycling in western Massachusetts, especially if you are not afraid to get off the pavement and venture onto some dirt roads. The Berkshires have countless scenic backroads, and this past weekend I was able to do another great ride that passed though the Beartown State Forest.
After meeting for breakfast, we all piled into Scott’s Eurovan and drove up to New Marlborough and parked on the green. We passed many other cyclists on the way there. We started out descending to Mill River, then wound our way to Sheffield. Scott’s crank arm was creaking, so we stopped off at the garage of dirt track racer Andy Bachetti which was located along our route. Andy had a 9 mm hex wrench and was nice enough to help us out. Thank Andy!
After arriving in Sheffield we headed northwest, eventually connecting to Jug End Road which is a nice dirt road that skirts the base of Mount Washington. After that we continued north toward Stockbridge.

Williamsville Road near Stockbridge
After arriving in Stockbridge we stopped on main street to refill water bottles. Beware of the $2 per bottle of water prices at the Stockbridge General Store. You are better off going to the gas station around the block.
After Stockbridge we climbed through the Beartown State Forest. Most of the climb from the north is a narrow paved road. Once we got up the hard part of the climb we took a left on Beartown Mountain Road which turned to dirt. For the most part, is was smooth packed dirt, but there were a few puddles and muddy spots.
There is a long downhill smooth dirt section that we took into Monterey where there is another country store. From Monterey we took another dirt road back to New Marlborough.

New Marlborough - Monterey Road
We were greatly helped navigating this route by using a Western Massachusetts Bicycle Map available from eMapStore, but we did notice the map had some roads listed as dirt that were paved.
View the complete photo set from this ride, and the photos on a map.
Route Map from MapMyRide.com



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Brent,
Another great day of Cycling and another detailed Blog to remember it by!
I am not doing any rides over 30 miles in the future without you as our Photo Journalist along.
The Beartown section was really nice I am glad we explored it.
Scott
That was a great ride and one that we should do again soon while it is fresh in mind. I think one more loop around soon will burn it to memory so that we can do it in the future without a map.
Certainly the best riding in the country!
I’d like to explore some of the other roads near Beartown State Forest and the Monterey area as well.