Mount Greylock Massachusetts’s Highest Peak

For me, one of the best parts of an adventure is what I learn and discover along the way. Often times, I start hiking a trail and find out either through other hikers or monuments, the historical significance of the route.

In 2013, on my quest to hike the highest peak in every U.S. state, I headed up to the Berkshires to take on Mt. Greylock. Standing at 3,491 feet, Mt. Greylock, is the highest peak in Massachusetts and one of the most beautiful mountains in the Northeast. A section of the Appalachian Trail also winds through Greylock’s maze of trees and brush. Mount Greylock is located in Adams, Massachusetts, which was first settled in 1762. Adams is ~130 miles from Boston and ~180 miles from New York City. In the 19th century, Adams and the surrounding area was the home for some of America’s greatest authors. Ralph Waldo Emerson, Henry David Thoreau, Nathanial Hawthorne, and Herman Melville all spent time hiking on Greylock and gained inspiration from it’s wondrous beauty.

There are a few options to reaching the peak of Mount Greylock. You can drive up or you can hike via one of the many marked trails. My ascent to the summit of Mount Greylock was via the Bellows Pipe Trail. This 5 mile round trip hike took me approximately 4 hours. However, don’t be fooled into thinking this will be a walk in the park! With heavy vegetation, uneven terrain, and steep ascents, this trail offers a respectable challenge. It is very important to thoroughly plan for this adventure as it is quite easy to get lost. There is a very remote feel to hiking Mount Greylock. At times, during my hike I feltlike I was in the middle of a Costa Rica rainforest16066408932_4a16593b41_o

As I neared the summit, I ran into a group of local hikers who shared a little history about the mountain. The author Herman Melville had lived just a short distance away in Pittsfield. Each morning when he looked through his study window, he had a clear view of Mount Greylock. Melville gained his inspiration for the book Moby Dick from Mt. Greylock’s long, saddle-like shape that he thought resembled a great whale. His love of Greylock didn’t stop at Moby Dick. He actually dedicated his 7th book ‘Pierre’ to the mountain with the words below:

”To Greylock’s Most Excellent Majesty,….for innumerable ages, been the one grand dedicatee of the earliest rays of all the Berkshire mornings, . . . will receive the dedication of my own poor solitary ray. . .”

I always get so inspired when I learn of the history behind an adventure. This aspect can really bring the experience to life and make your trip that much more memorable. If you are ever visiting the Berkshires or planning a trip to Massachusetts be sure to visit Mount Greylock, you won’t be disappointed.

If you would like to learn more about our adventures click HERE or if you would like to talk history and adventure shoot us an email at We always love a good chat!

I look forward to seeing you on the trail!



Jeff Bonaldi
Founder & CEO
The Explorer’s Passage

About Jeff Bonaldi

Jeff Bonaldi is the Founder and CEO of The Explorer’s Passage, a premier adventure travel company. His mission is to provide travelers with the opportunity to transform their lives and the planet through the power of adventure.

Learn more about Jeff’s story and his company HERE.

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