Pittsfield State Forest
Pittsfield State Forest is a great place to ride mountain bikes. For those who don't know the state forest, it's roughly 8 x 2 miles (10,000 acres) along the Taconic Ridge, sandwiched between downtown Pittsfield and the NY state line. A DCR trail map is available at the state forest, and the following description uses trail names from that map. The best map for "the big picture" is the Rubel Bike Map for Western Massachusetts (bikemaps.com). To get to the state forest, go west on West Street from downtown Pittsfield and follow state forest signs (via Churchill and Cascade Streets)
If you like to camp, consider camping in the state forest from May to October. I prefer the sites on top of the ridge near Berry Pond. The downside to the top of the ridge is that there's only a composting toilet and no running water. The good news is that the relative isolation is wonderful; take your shower and get drinking water in the camping area at the bottom of the ridge.
The most interesting rides in Pittsfield State Forest are north and south from the top of the ridge near Berry Pond, starting out in either direction on Taconic Skyline Trail (the parallel Taconic Crest Trail is hiking only). Other than the camping, the biggest advantage of starting from Berry Pond is that the Taconic Skyline Trail, which has a rough surface because of motorized vehicle use, is slightly downhill in both north and south directions from Berry Pond and is thus easier to ride.
To ride your bike to the top of the ridge near Berry Pond from the entrance to the state forest, ride Honwee Trail towards the top of the ridge, then use the paved road the rest of the way to the top. Honwee Trail is actually a loop trail, but stay on the section closest to the paved road, which is only moderately steep. The Honwee Trail leg that is furthest from the paved road is extremely steep. Once on top of the ridge, there's a spectacular view west into New York State. Before heading north or south, ride some of the trails and roads in and around the camping area and pond.
The loop north follows Taconic Skyline Trail along the ridge to Potter Mountain Road. Turn right onto Potter Mountain Road and immediately look for Potter Mountain Trail descending to the left. At the bottom, turn left to visit Balance Rock--quite spectacular as balanced rocks go in New England. Retrace your route from Balance Rock and follow Balance Rock Trail back to the bottom of Honwee Trail near the state forest entrance. There's an interesting variation to this route by turning right to follow Churchill Brook a short distance, then crossing the brook onto a sweet single-track trail. Just don't climb back up the ridge.
The trip south from Berry Pond can be done several ways. The toughest part of riding south is finding the right trail down from the ridge (hint: descend first to West Street, then ride the CCC Trail if you want to go further south). To return to Berry Pond, you'll either have to retrace your route--tough because it's uphill--or make a loop by riding paved roads.
The most interesting ride south from Berry Pond is to drop a vehicle at the campground at October Mountain State Forest (alternatively, leave your vehicle in the center of Lenox). Start the ride from Berry Pond in Pittsfield State Forest. Ride south on the trail system to US 20 across from Hancock Shaker Village. Turn right onto US 20, then immediately left and ride back roads (mostly dirt) over Lenox Mountain to Lenox via Osceola, Dunbar, and Reservoir Roads. Do a side trip on a jeep road to the fire tower on Lenox Mountain, if desired (I saw black bear when I did this). As you approach Lenox, ride through John Drummond Kennedy Park, which is a wonderful mtb destination in its own right, by entering the "back door" from Reservoir Road. From downtown Lenox, ride east to October Mountain State Forest. If you ride east on Housatonic Street from Lenox, you can avoid traffic by crossing the Housatonic River on a footbridge just north of the October Mountain State Forest campground entrance.
If you've still got legs, ride within October Mountain State Forest, but be advised that you're at the low point within the state forest and it's a pretty tough climb to the top.
Over the last couple of years Berkshire NEMBA, working with DCR staff, have put in a highly enjoyable network of trails in the eastern section of the forest. A very detailed map of these trails is available as a handout at the guard shack at the forest's entrance.
By Jim Logan