About Cheshire Harbor Trail
This trailhead for the Cheshire Harbor Trail will supply visitors with many options for an enjoyable day of outdoor recreation in the Berkshires. Numerous multi-purpose trails leave from this trailhead, offering different experiences at all times of the year.
The Cheshire Harbor Trail, a 6-mile cross-country-skiing and hiking trail, leaves directly from this trailhead and heads toward the summit of Mount Greylock. The first part of the trail is a flat, gravel path. Then, the trail quickly inclines as it continues toward the peak. Once at the top, visitors will access panoramic scenic views of Western Massachusetts. A lodge also sells food and drinks there, making the summit ideal for a lunchtime picnic.
For an easy hiking trail, visitors can travel on the Moser Farm Loop. This loop, which leads down to the Gould trailhead and back, is a family-friendly trail that ambles over small hills. Eventually, the trail reaches an open meadow with views of Mount Greylock rising in the west.
The Grass Hopper Trail, a small mountain biking loop, is also easily accessible from this trailhead. With high berms and small jumps, the trail is perfect for bikers of all ages hoping to improve their skills.
Parking is near the end of West Mountain Road. The trailhead also provides access to an unmaintained snowmobiling trail in the wintertime.