Elevation Gain: 2500 Feet
Distance: 5.9 Miles
My friend Levi, and I had planned to do a hike to the summit of Dewey and pick up Sky Top along the way. However, something came up for Levi at the last minute so I decided I would go alone. It would be my second time visiting Dewey and my first time climbing Sky Top. Mount Dewey is located in Underhill, Vermont. It is on the New England 3000 Footers and the New England 1000 Highest.
My plan was to start from Stevensville Trailhead, hike the Overland Ski Trail to the Long Trail and from the Long Trail, bushwhack to the summit of Dewey. If time allowed, I would continue on to Sky Top, a peak on Peakbagger.
I started early, around 7:45, and began walking the Overland Trail. The trail was very distinct. However, about two-thirds of the way up, the trail began to disperse. I then bushwhacked to the Long Trail. I crossed the Long Trail and began bushwhacking through thick hobble towards Dewey which I could see the entire time. I began bushwhacking to the west ridge of Dewey which I would hit and walk up to the summit. I hit the distinct spruce line and quickly hit a small blowdown which I crossed quickly. I began crawling through thick brush and hit the ridge. I then followed the distinct ridgeline to the summit where two register jars sat and red blazes led into the brush
The Forehead of Mount Mansfield from the start of the bushwhack just after the Long Trail Crossing
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Birch Glades above the hobblebush area
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A view through the trees above the blowdown and in the spruce. This is looking towards Lake Champlain.
The summit registers on Mount Dewey Elevation: 3370'
Me pointing to the register
My name in the register from 2017! Has not changed much up here.
From the summit of Dewey, I began to hike towards Sky Top. What I thought would be a rough bushwhack ended up being way easier than I thought it would be. From the summit, I spotted a red diamond blaze. I began to follow them and the trail became more and more distinct. It became stepper and stepper until I reached the col and found the trail shown on Gaia GPS. I turned and saw a sign labeled KINGSFORD TRAIL leading up to Mount Dewey. There was also a sign pointing downhill saying BURT. I began walking on the snowshoe trail toward Sky Top and got views of Mount Mayo and Mount Clark. I made it to a point where I began a short bushwhack to the summit of Sky Top which had no register. I then turned around and followed the same route back to Dewey. I dropped off the west face of Dewey and encountered thick brush where I could not see my feet I also got cliffed out multiple times. I managed to make it back to the Long Trail and then took the same route down to the distinguishable section of the Overland Trail and out where my dad picked me up a few minutes later.

The Kingsford Trail sign with the red blazes leads to the summit of Mount Dewey.
BURT sign pointing downhill
A pano on the way to Sky Top. From left to right. Bolton (Partially behind a tree), Clark (Partially behind a tree), and Dewey.
Bolton from another point
A zoom of Mt Clark
Selfie on the summit of Sky Top! (Elevation 2980') Nothing notable here and just off the trail.
A cool flower on the way down. I believe it is a Trout Lily in bloom.
This was a good hike. I was able to grab a new peak and revisit another one. It being a nice day was a bonus. I was in the woods for just over four hours. These two peaks offer some difficult terrain and I was glad to be out there. Happy hiking!
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