Climb Mt. Greylock
The highest peak in Massachusetts
Climbing Mt. Greylock is the ultimate Berkshires hiking challenge—and the ultimate payoff! You really earn the summit of Massachusetts’ highest peak when you hike it! One of the best views in all of New England awaits you when you reach the summit at 3,491 ft. Best of all, it’s not as hard as you’d think. Most hikers can do it!
We’ll climb up from the valley 2,000’ below and feel great under the trees as we hike up. It’s a little adventure, and we even get to hike on the world-famous Appalachian Trail. Certainly the highlight is the stunning vista overlooking the beautiful Berkshire Mountains, the Taconic Range, the Adirondacks, the Green Mountains to the North, and even the Whites in New Hampshire. You can see 5 states on a clear day!
I’ve done it dozens of times since I moved here in 2021. Great exercise, and pretty doable for many (if not most!) hikers. Now I’m not saying it’s the Matterhorn, but in my estimation it’s a damn fine achievement to say you’ve climbed Greylock! And it’s always fun and good exercise—an awesome way to be outside in nature for half a day!
🥾 Check out the different ways we can hike it 🠋
Choose Your Greylock Adventure:
🥾The Classic Ascent (4 hours) – From Greylock Glen IN Adams, MA
This half-day loop packs the full experience Greylock experience. As you drive up to the Greylock Glen area in Adams and you’ll see the mighty East Face of Greylock right in front of you. You can see exactly where we’ll be going. But trust me, it’s not as hard as it looks! We’ll ascend a bit over 2000’ on Gould Trail, a steady, scenic climb that winds through variable green forests and offers a few sneak peeks before the main event. As we approach the summit, we’ll join the Appalachian Trail and make the final ascent through rare boreal forest before we get to the unforgettable summit view.
We’ll chill at the summit, soak in the view take some pics, check out the Veterans Memorial, and have a snack. Then we’ll descend via either the Cheshire Harbor Trail (gentler option) or the legendary Thunderbolt Trail – once home to an old-school ski racecourse and now a steep, thrilling descent.
Best for: Hikers of all abilities in decent to good fitness level, looking for a solid workout and epic views without committing to a full-day trek. It’s 5-7 miles round trip, 3.5 to 5 hours—depending on our speed.
$60 per hiker, groups 4-6
$75 per hiker, groups 2-3
$100 per hiker, solo hiker
🏞️ The Full Day Challenge (6–8 hours)
Ready to level up? Choose from several longer, more rugged routes that take you deeper into the Mount Greylock State Reservation, combining a longer, strenuous climb, remote forest paths, and extended time on the iconic Appalachian Trail.
From North Adams: Climb via Bellows Pipe Trail and the Appalachian Trail to the summit, then descend via Bernard Farm Trail – a loop that’s scenic, quiet, and deeply rewarding.
From Williamstown: Hike up the Hopper Trail, cross the summit via the Appalachian Trail, take in the amazing views, then descend the beautiful and varied Haley Farm Trail, taking in another stunning vista (background image). You’ll get everything from serene woods to tumbling streams.
Longer Loops: Interested in even longer journeys up Greylock? We can start from the Appalachian Trail in North Adams, or Money Brook Falls Trail to Hopper Trail. We can also do a loop from Roaring Brook trailhead further south that takes us down via Stony Ledge Trail (with the amazing view you see here!).
Best for: Hikers in good shape with prior trail experience, looking for a full-day adventure and deep immersion into Greylock’s natural beauty.
$110 per hiker, groups 3-5
$150 per hiker, groups of 2
$200 per hiker, solo hiker
🏔️ Fun Facts ABout Mt. GReylock
⛰️ Highest Peak in Massachusetts!
At 3,491 feet, Greylock is the tallest mountain in the state. On a clear day, you can see up to 90 miles in all directions — into five states!
✍️ Literary Legends Inspired by It
Herman Melville could see Mt. Greylock from his home in Pittsfield and it helped inspire the great white whale in Moby-Dick. Nathaniel Hawthorne also spent time here, writing and wandering.
🏛️ The Memorial Beacon
At the summit stands a towering 93-foot Veterans War Memorial, topped with a glowing beacon — like a lighthouse for the mountains. You can walk up the cool spiral staircase for an even better 360° view of the Appalachians surrounding you! It triumphantly honors all the soldiers from Massachusetts who have given their lives defending the nation
🏞 The Appalachian Trail Runs Right Over It
Thru-hikers and local adventurers alike cross Greylock’s summit as part of the 2,190-mile Appalachian Trail. You’re walking with legends.
⛷️Historic Thunderbolt Ski Trail
Built in the 1930s as a New Deal project, the legendary Thunderbolt was one of the first ski trails in North America. Skiers would bomb down the mountain at breakneck speeds — no lifts, no fear, just wool pants and guts. It’s still a favorite for backcountry skiers, snowshoers, and hardcore hikers today, maintained by the great Thunderbolt Ski Runners.
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