At 16,500-acres, October Mountain is the largest state forest in Massachusetts. The name was inspired by the beautiful foliage and colors of these hills in fall. Trails are available for every level of experience. This particular route follows dirt roads through the forest and takes advantage of the steep elevation changes between the Housatonic River and the interior of the state forest. Beginning at the forest headquarters, you will follow the flat Woodland Road until you reach New Lenox Road where the climb begins. You will make a steady climb for about a mile, ride along the top of the mountain where there are beautiful views, and then make a long and steady descent. There is minimal technical riding involved as the entire route is on dirt roads, but it is the extended ascent and descent that make the ride more challenging.