Get access to everything we publish when you sign up for Outside+.
This 9-miler parallels a stream and passes a ski area nestled into the Taconic Range before tackling a 1,200-foot climb up to Stony Ledge (good views of the day’s summit await). From here, the climb continues east on Hopper Trail to Mount Greylock (3,491 ft.), the highest point in Massachusetts. The peak offers big views to the neighboring Berkshires, and another state highpoint checked off your lifelist. Backtrack to the trailhead, or take an alternate loop down on the Overlook Trail.
-Mapped by Trung Q. Le
- Distance: 7.2
Location: 42.6376609802246, -73.2194976806641
Park at the turnout near the end of Roaring Brook Road and walk parallel to Roaring Brook down a path towards the trailhead.
Location: 42.637321472168, -73.2187728881836
Cross a small footbridge over Roaring Brook. From here, the trail criss-crosses the stream en route to the next major trail intersection.
Location: 42.6348991394043, -73.2137985229492
Cross another small footbridge over Roaring Brook; depending on the season, a local ski area may be visible to the south.
Location: 42.6352310180664, -73.2127532958984
Cross another small footbridge over Roaring Brook.
Location: 42.6352005004883, -73.2122268676758
Continue straight (bearing left @ the Y-junction) on Stony Ledge Trail. The Roaring Brook Trail continues to the right, offering an alternative approach to Greylock that circumvents this route’s 1.5-mile, 1,200-foot ascent to the top of Stony Ledge.
Location: 42.6452484130859, -73.1949996948242
Continue straight @ 3-way junction on the Stony Ledge Trail. The Haley Farm Trail shoots off to the north.
Location: 42.6442985534668, -73.1938018798828
Stoney Ledge overlook: Look East to see Mt. Greylock’s Orb Tower. From here, go to descend along Sperry Road, a wide dirt road. There are several campsites alongside the road.
Location: 42.6337509155273, -73.1888809204102
Continue straight on Sperry Road. The Hopper Trail shoots off north.
Location: 42.6328811645508, -73.1880798339844
Continue straight on Sperry Road. To the right, Roaring Brook Trail rejoins this route, and to the left the Hopper Trail continues south after a brief strech on Sperry.
Location: 42.6321296691894, -73.1872634887695
Continue straight on Sperry Road. The March Cataract Falls trail shoots off to the left.
Location: 42.6309013366699, -73.1871795654297
From here, numerous trails intersect in several different directions. Continue on Sperry Road and look for Hopper Trail signs on the left. Turn left on Hopper to leave Sperry Road behind and continue east on a gentle uphill grade.
Location: 42.6339683532715, -73.1768188476562
Go right @ 3-way junction to continue on the Hopper Trail.
Location: 42.6329002380371, -73.1768188476562
Turn left to continue on the Hopper Trail.
Location: 42.6329498291016, -73.1743011474609
Go left @ 3-way junction, continuing on the Hopper Trail. The Cheshire Harbor Trail shoots off to the southeast.
Location: 42.6339492797852, -73.1717300415039
Continue on the Hopper Trail, passing a small pond with a shelter on the eastern end.
Location: 42.6340713500977, -73.1706466674805
Cross the road and continue straight on the trail.
Location: 42.6372489929199, -73.1658325195312
Mount Greylock summit (3,491 ft.). Continue back down the way you came or take the Overlook Trail and rejoin the route at Waypoint 12.