Greylock. The Appalachian Trail travels 90 miles in Massachusetts as the trail winds through the Berkshires. After about 3 hours of driving from each direction, we all got to spend a wonderful 24 hours together. The New England Hundred Highest is a list of the hundred highest summits in New England, used in the mountaineering sport of peak bagging.The list is a superset of the New England Four-thousand footers, with the same requirement that each included peak must have 200 feet (61 meters) of topographic prominence ("optimistic" prominence, equivalent to 160 ft (49 m) of "clean" prominence). Zouhan Zeng/Google Images. Mount Greylock is located in the Berkshire Mountains, and is the highest mountain in Massachusetts. From Monument Mountain, Mount Greylock's profile looked like a whale to Herman and it was Mount Greylock that inspired the great white whale he named, Moby Dick.) For instance, Alaska could be regarded as the highest state because Denali, at 20,310 feet (6,190.5 m), is the highest point in the United States . And getting to Connecticut’s highest point requires climbing up two mountains, then climbing down to the high point. It is located in northwestern Massachusetts. Everet… The trail passes over the highest point in the state at Mount Greylock with an elevation of 3491 feet. Greylock website These directions are taken directly off of Massachusetts State Parks website. Fitch 3,110 4 Mt. However, Colorado, with the highest mean elevation of any state as well as the highest low point, could also be considered a candidate for ” highest state”. Williams 2,951 5 Spruce Mountain 2,710 6 Misery Mountain 2,671 7 Brodie Mountain 2,621 8 Mt. Summary Massachusetts is home to the Berkshires, a range covering much of the western portion of the state. Directions: Mt. The trail travels over hills, valleys and through towns and hamlets of the Berkshires. Mountain Elevation (ft) 1 Mt. NE 100 Highest NH 4,000 Footers NH 100 Highest NH 52 With A View NH Belknap Range NH Ossipee 10 Links Search Trail Conditions Trip Log Sunrises Sunsets About: Massachusetts Mountains & Peaks. Mount Greylock is the tallest mountain in Massachusetts at 1,063 meters or 3,487.5 feet. The AT passes through the towns of Dalton and Cheshire. For a quick trip, we decided to all drive to North Adams, Massachusetts on a cool spring Friday, and spend a Saturday hiking Massachusetts tallest mountain - Mt. Latitude/Longitude 42.638 / -73.166. Plus the trail to the summit (rather than the highest point) of Mount Frissell is near an attraction more interesting to some: the New York-Connecticut-Massachusetts tri-state marker. Mount Sugarloaf is an 800 foot mountain in South Deerfield and is one of the tallest points in central Massachusetts. We were there April 19-20, 2013. Greylock 3,491 2 Saddle Ball Mountain 3,238 3 Mt. 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