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Hiking trail

Hiking in the Berkshires: Cheshire to Mount Greylock Summit

Hiking trail · Massachusetts
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    Photo: Chase Marston, Macs Adventure
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Spend the day walking through stunning woodland terrain while climbing steadily to the summit of Saddle Ball Mountain. Continue on an iconic Appalachian section to reach the summit of Mount Greylock, Massachusetts’s highest peak and finest views.

13.1 km
5:00 h
831 m
82 m

Quickly leave town behind as the trail enters the quiet woodlands. Spend the first few miles in the rural outskirts of Cheshire, passing hilltop homes and rolling fields. Then get into the rhythm of the climb as the trail begins trending upward toward Saddle Ball Mountain. Though the trail is mostly ascent, the grade is relatively gentle with a few steeper sections. Wind through dense pine trees and open hardwoods groves, and balance on the long boardwalks through the wetlands. As you approach Mount Greylock, notice the pronounced Veterans War Memorial tower peaking above the tree line, a sign that your destination is nearing. The last mile is steep, but the reward is worth the challenge! Follow the AT straight to the tower to enjoy the views before settling into Bascom Lodge for the evening.


Note, there are no lunch facilities on the way, but Bascom Lodge offers a full lunch from 11-4:30 every day. 

Author’s recommendation

Eat a full breakfast, as the day is predominantly uphill. And, be sure to bring food as there are no opportunities to get food along the way. User
Chase Marston
Updated: April 25, 2019

Highest point
1066 m
Lowest point
303 m

Safety information

Though the trail is well marked with the iconic Appalachian Trail white blazes, it can be easy to temporarily lose the trail or begin following a false trail.  Any false trail will quickly end, so simply retrace your steps to the trail and look for the white blaze.


After or during rain, the trail can become muddy, slippery, and harder to locate. Be extra cautious on wet leaves, rocks and mud to maintain balance, and pay extra attention to the white blazes to stay on the trail. Furthermore, rain will cause the streams to flow higher, making the crossings slightly more challenging. Remember, a wet boot is better than falling in the steam and potentially hurting yourself. If there is not a clear safe dry route across, find a safe wet route. 


After or during rain, the trail can become muddy, slippery, and harder to locate. Be extra cautious on wet leaves, rocks and mud to maintain balance, and pay extra attention to the white blazes to stay on the trail. Furthermore, the steams will tend to run higher, so some of the crossings may present a slightly higher challenge.


Various hunting seasons will overlap with the hiking season, so always wear a bright color in the spring and fall. Familiarize yourself with which hunting season might occur during your trip on the following website: (OR)


As always, be sure to check the weather before departing for the hike – New England weather is notoriously fickle, so always be prepared with proper layers and rain gear.


Bring hiking boots that are both comfortable and worn.

Always bring rain gear as the New England weather can quickly change. Bring also an extra layer or two, plus a warm mid-layer.

Bring dry, extra socks as they can be helpful to prevent blisters.

Though poles are not necessary, they are recommended for balance in uneven terrain and over steams as well as assistance with climbing and descending the steep hills.

Basic medical supplied, including blister protection.

Tips, hints and links

Points of Interest


Veterans War Memorial Tower 

An iconic symbol of the Berkshires, this stunning 93-feet tall tower is the ornament atop Greylock's summit. Its perpetual lighted beacon was once the strongest in Massachusetts, and can be seen from over 70-miles away. 

Bascom Lodge

A mountain lodge built in the 1930's using native materials of Greylock schist and red spruce, this center provides shelter, overnight stays, wonderful dining experiences, and a display of unique architecture. 


Food and Water

There will be not opportunities to refill water or acquire food along this day’s route. Be sure to bring enough of both for the entire walk. This includes 1-2 liters or water, a full lunch, and enough snacks keep you fueled. We recommend bringing a water purification method in the event of an emergency. Call our office or contact your local outdoor store for options.


Harbour House Inn B&B (317 m)
42.577667, -73.151948
18T 651661 4715572


Bascom Lodge, Mount Greylock

Turn-by-turn directions

0.0 miles – Depart the Harbour House B&B and return to Rt 8., TURN RIGHT to head south the way you came the previous day. 


0.85 miles – TURN RIGHT onto the Appalachian Trail North (ATN). The trail will quickly begin climbing gently into the woods.


1.6 miles – Continue STRAIGHT ON across the road to stay on the ATN. The trail will climb gently for about .5 miles before getting steeper for a short section.


4.2 miles – Continue STRAIGHT ON over the Old N. Adams Road. The trail will begin climbing steadily from here to Saddle Ball Mountain.


4.8 miles – BEAR LEFT on the ATN at the intersection for the Mark Nopel Shelter.


5.3 miles – Continue STRAIGHT ON the ATN following signs for Greylock as a trail to Jones Nose enters from the left.


7.2 miles – Come to the Greylock access road, TURN RIGHT across the parking area to rejoin the ATN following signs for Greylock Summit.  


7.5 miles – Continue STRAIGHT ON across the access road following signs for the ATN and Greylock Summit.  


7.7 miles – Just after passing a pond, the trail comes to a large intersection of three trails and three roads. BEAR LEFT and follow signs for Greylock Summit, Bascom Lodge, and the ATN


8.1 miles – Continue STRAIGHT ON toward the summit. Come to the access road roundabout – from here, celebrate at the summit’s Veterans War Memorial Tower, or go check in at the Bascom Lodge. Be sure to take in the stunning views of the Berkshires and revel in your achievement!


all notes on protected areas

Arrival by train, car, foot or bike

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13.1 km
831 m
82 m


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