Mount Greylock | Massachusetts #1

The Start of My State High Point Journey

At 3,491 feet, Mount Greylock is the highest point in Massachusetts, ranking #31 among U.S. state high points and marking my first official summit in the journey to visit the highest point in every U.S. state and the District of Columbia.

Located in the Berkshire Mountains of western Massachusetts, Mount Greylock stands apart from many state high points in that it’s a true hike—and, on a clear day, offers views into five states. I tackled this inaugural summit alongside my sister, Vicki, making it an especially memorable start to the adventure.

The hike

We completed a loop totaling about 6.7 miles, which took roughly 4.5 hours, including stops. One of the unique aspects of Mount Greylock is that sections of the hike overlap with the Appalachian Trail, adding a bit of long-distance hiking history to the experience.

The trail steadily gains elevation without feeling punishing, and the payoff at the summit is well earned. Even before reaching the top, the sense of place—remote, rugged, and distinctly New England—sets Greylock apart.

On the summit

The summit of Mount Greylock is home to the Veterans War Memorial, a striking stone structure that anchors the high point. On clear days, the views stretch across Massachusetts, New York, Vermont, New Hampshire, and Connecticut, making it one of the more scenic state high points in the Northeast.

Standing there, it felt like the right place to begin—challenging enough to feel earned, scenic enough to inspire what was ahead, and symbolic in a way that only a first summit can be.

Pictures (clockwise): Me on the summit | Looking up at the summit | The Veteran’s War Memorial on the summit | View from the summit

Final thoughts

Mount Greylock was the perfect introduction to highpointing: a real hike, big views, and a sense of accomplishment that made the idea of tackling all 50 states (plus D.C.) feel both ambitious and achievable.

After the hike, we headed back toward upstate New York and capped off the day with a stop at Udderly Ice Cream in West Sand Lake, NY. As soft-serve fans, it was exactly the post-hike reward we didn’t know we needed—and a great way to end the day.

Photos: Udderly Ice Cream, West Sand Lake NY | Post-hike treat!

So one down and fifty more to go (including the District of Columbia). Alongside this high-point journey, I’m also making a point to visit the Best State Park in Each State, as selected by Morgan Love, a writer for The Discoverer, one of my favorite travel blogs.

Catch you on the summit!

Date of Climb: 21 April 2023