Cheshire Harbor Trailhead — Adams, Massachusetts This 6.4-mile out-and-back trail near Adams, Massachusettsleads to the summit of Mount Greylock, Massachusetts’ highest peak. Generally considered a challenging route, it takes an average of 3 h 51 min to complete. The first part of the trail is a flat, gravel path, thoughthe trail starts very wide and gets rocky, with a steady incline to the top that in some places does get a bit steeper. This is the easiest and shortest ascent route from the base to the summit of Mount Greylock, with spectacular views at summit. Signs at the top call out points of interest that are visible on a clear day, including the Mount Monadnock in New Hampshire and Mount Wachusett in Massachusetts. There is also an easy hiking trail, the Moser Farm Loop, and a mountain biking trail, the Grass Hopper Trail, accessible from this trailhead.