Cheshire to Mount Greylock Trail

The Cheshire to Mount Greylock Trail is a 23.4 km trail that starts in Cheshire, Berkshire County, Massachusetts. Based on our data, the hike is graded as Difficult. For information on how we grade trails, please read measuring the difficulty of a hiking trail on hiiker. Also, check our latest community posts for trail updates. This hike can be completed in approx 6 hrs 35 mins. Caution is advised on trail times as this depends on multiple variables. For more info read about how we calculate hike time.