Tumbledown Mountain is one of the most popular trails in Maine for its challenging rugged hike, the infamous “fat man’s misery” section, the excellent views from its summit and ridge line and the gorgeous alpine pond situated between the top of Tumbledown Mountain and Little Jackson Mountain.
The loop trail, ascending the steep and difficult Tumbledown Mountain Trail to the west and east summits, then down to the alpine pond on the ridge trail, and returning to the road on the more gradual Brook Trail is 5.2 miles and will take about 4 to 5 hours to complete.
The trail heads for Tumbledown Mountain and Brook Trail are 1.3 miles from each other on an unpaved road, so unless you have two cars, that makes the total loop 6.5 miles. There are parking areas at both trail heads so you can begin or end your hike with the walk on the road.
The Tumbledown Mountain trail is steep and very rugged, with a total elevation gain of about 2,000 feet, so this one’s not for beginner hikers.
Tumbledown Mountain Trail Map
Tumbledown Mountain Trail Head Directions
The trail heads are located on Byron Road, an unpaved road that connects Route 142 in Weld and Route 16 in Byron, between Rumford and Rangeley. The Google Map above is for the brook trail head. The other trail head is 1.3 miles down the road going toward Byron.
Tumbledown Mountain Trail
The Tumbledown Mountain trail ascends steeply through the woods, with plenty of exposed roots and rocks on the trail.
After about a mile, you’ll ascend over a big hump, the trail will very briefly level out, and you’ll have a fine view of the summit appearing almost vertically in front of you.
The steepest portion is in the next mile, and just before reaching the summit you’ll go through “fat man’s misery”, a narrow cave / chimney you’ll climb through with the aid of iron rungs.
It took me 2 hours (1.8 miles) to reach the summit. Turn left for a short trail to the west summit, where amazing views await, before continuing on the ridge trail to the east summit and Tumbledown Pond.
Tumbledown Ridge Trail & Tumbledown Pond
After enjoying the views from the west summit, turn around and follow the ridge trail to Tumbledown Pond. This was my favorite part of the hike as it provided nonstop awesome views. After descending down to Tumbledown Pond, however, the solitude was lost. It was like a party there, full of people. I think that a lot of people just do the brook trail to the pond as an easier (but still challenging) out-and-back hike and have lunch at the pond. Regardless of the crowd, it’s still amazing to stand at this little pond between Tumbledown Mountain and Little Jackson Mountain, which also has a trail to its summit.
Brook Trail
The Brook Trail is the least interesting of the trails on this loop. It gradually descends through the woods, crossing the brook several times, down to the road. It took me about an hour and a half to descend the 2 mile trail to the road. Fortunately, we had a car at both trail heads, but otherwise we would’ve had to walk another 1.3 miles on the dirt road back to the Tumbledown Mountain trail head and parking area.
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Looking for more great hikes in Maine? Check out the best day hikes in the Moosehead Lake Region & 100 Mile Wilderness of Maine.
Fat Man’s Misery is actually a part of the abandoned Chimney Trail, which is a left off of the Loop Trail about 2 miles in.. has metal rungs like the tunnel, but also requires the use of a rope that’s been left in place and usually replaced after so many years… not a trail for the average hiker.
Any markers or landmarks that point out when to turn left for Chimney Trail?
-Currently the Tumbledown Trail Steward through the Maine Conservation Corps. Also was the steward here back in 2020.
Fat Man’s Misery is indeed a part the modern Loop Trail, not the Chimney Loop. It does not need a rope but would probably help for less experienced hikers and for wetter days. A lot of people think the rope climbing part of the Chimney is called Fat Man’s Misery. It is not.
Also, the Chimney Trail does NOT break off 2 miles into the trail, considering the modern Loop Trail is roughly 1.5 mile. The break off is only a mile in once you hit the “false peak”. This trail is never maintained, and rescue efforts will be a lot slower than just sticking to the modern trails.