From the trailhead, head north on the blue-blazed Guilder Pond Trail, almost immediately crossing a creek on a split log footbridge. The trail follows the shore of Guilder Pond, which is 2,048 feet above sea level, making it the second highest pond in Massachusetts. At times, the trail heads into the hemlock forest, then returns to the pond. After walking for 0.6 mile (three-quarters of the...
Hike Description:
From the trailhead, head north on the blue-blazed Guilder Pond Trail, almost immediately crossing a creek on a split log footbridge. The trail follows the shore of Guilder Pond, which is 2,048 feet above sea level, making it the second highest pond in Massachusetts. At times, the trail heads into the hemlock forest, then returns to the pond. After walking for 0.6 mile (three-quarters of the way around the pond), an unmarked side trail on the right leads you to a large rock ledge overlooking the entire pond. This is a great place to take a break.
When you’re ready to continue, return to the Guilder Pond Trail and turn right. In another 500 feet, you'll come to a junction with the white-blazed Appalachian Trail (A.T.). Turn left onto the A.T., which you will follow all the way to Jug End. In half a mile, you'll pass a sign for the Hemlocks Shelter, rock hop over a creek, then reach a blue-blazed side trail that leads to the Glen Brook Shelter.
In about .75 mile keep left on the AT and rock hop over a creek as the blue-blazed Elbow Trail goes right. The Elbow Trail terminates at the Berkshire School on MA Route 41.
In another half mile you might be tempted to leave the trail to the right, following faint unofficial paths in search of views but resist the urge as there is no need to trample the vegetation as others have done. Before you know it, the Appalachian Trail will deposit you directly on to a rock outcrop at the summit of Mount Bushnell for unobstructed views of the Massachusetts countryside. Look towards the horizon for the highest peak, Mount Greylock, the highest mountain in Massachusetts, about 40 miles away.
Where the trail ascended and descended along a fairly smooth trail up to this point, you will now find the path becomes more rugged with steeper inclines and some short rock scrambles. There will be more views to your right as you continue on, especially during times of no foliage, while traveling along the ridge. At the 4.4-mile point, a large cairn indicates you have reached Jug End but continue on briefly, stopping before the trail drops precipitously, to enjoy the views. Turn around and head back the way you came. Continue straight when the Guilder Pond Trail joins the AT on the boardwalk resulting in white and blue blazes the rest of the way to the upper parking lot.


Hike through old growth forest along Guilder Pond, the highest natural body of water in Massachusetts, then follow the Appalachian Trail along Mount Bushnell’s summit views on the way to Jug End.