Looking across Tumbledown Mountain from Tumbledown Ridge. Mount Washington and others are visible in the distance.
Photo by Ryan Linn
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Tumbledown Mountain Double-Loop

Yesterday, I did a day-hike that ended up being a lot more punishing than I thought it would be, but it was one of the most rewarding I’ve been on in years. The hike was two full loops in the Tumbledown range near Weld, ME, each of which makes for a challenging full-day hike.

Ryan Linn       Trip Report       09/19/2013
Ryan Linn
Trip Report
09/19/2013

Yesterday, I did a day-hike that ended up being a lot more punishing than I thought it would be, but it was one of the most rewarding I’ve been on in years. The hike was two full loops in the Tumbledown range near Weld, ME, each of which makes for a challenging full-day hike.

The weather this week has been phenomenal for hiking, and I’d been itching to get back to Tumbledown after my last visit, two years ago. After this trip, I’m pretty confident in saying that Tumbledown (along with Little Jackson Mountain) is one of the most beautiful places on the planet.

A view of distant mountains with blue skies and green trees.
Looking out at Tumbledown from Little Jackson Mountain.
Photo by Ryan Linn

I arrived at the trailhead a little late due to missing the first turn onto the road around Webb Lake, and then taking a detour around a washed out road. But I was on the trail by 9:30, choosing to go up Little Jackson Mountain first, since I hadn’t been up that mountain before.

The trail was like many trails in Maine– rocky and rooty, and generally beautiful, crossing a bunch of brooks and streams that might make for good head-dunking in warmer weather. Soon enough, the trail started to climb a fairly steep grade, becoming a long stair-master as I approached tree-line.

Once above tree-line, though, I could tell this was going to be an amazing day. For almost a mile from the junction with the Jackson Mountain Trail, the Little Jackson Trail walks on completely exposed granite with sweeping views in all directions. It’s not a terribly high mountain, at 3400 feet, but it had a similar feel to Saddleback Mountain (which was visible nicely just to the north).

A stiff, icy breeze kept me nice and cool, while the clear skies gave me a pretty good sunburn. The views from the mountain were just extraordinary– aside from the unique perspective on Saddleback Mountain, there was also a clear view to Mt Abraham and Sugarloaf, and in the other direction I could see much of the Mahoosuc Range, the Presidential Range, and the Bemis Range.

I’m sure there was a lot more that I couldn’t identify, but that’s plenty right there.

A view from a rocky ridge of distant mountains and lakes.
Mount Blue and Webb Lake from Little Jackson Mountain.
Photo by Ryan Linn

After some time up top, I got cold enough that I had to descend, then take a quick trip up to Jackson Mountain. The taller of the two peaks doesn’t have an open summit, and the trail looked like it didn’t get much use.

There was an interesting installation up top, with a small building and a large set of solar panels. I couldn’t tell what the purpose was, but either way I’ll stick with the shorter peak next time.

Next up, the Pond Connector Trail to Tumbledown Pond. This trail was also somewhat overgrown, but it went through a pretty stand of birch that was starting to change color, so I can’t complain.

When I arrived at Tumbledown Pond (one of three highlights of the entire area– how can you get much better than an alpine pond with a view all the way to Mount Washington?), I saw the first two people of the day. They were fly-fishermen rather than hikers, and both were having pretty good luck despite the brisk wind blowing their lines around.

By now it was about 1 in the afternoon, and I’d already gone about 8 miles. I was pretty tired. But why stop now?

A view of a nearby mountain with blue skies and green trees.
Little Jackson Mountain as seen from a ridge on Jackson Mountain.
Photo by Ryan Linn
A distant hiker stands on the edge of a blue alpien lake surrounded by green trees.
A few fly fishermen were having a good time at Tumbledown Pond, despite the wind.
Photo by Ryan Linn
A view shows a nearby rocky mountain covered in green trees.
Heading up Parker Ridge with a view of Tumbledown Pond and Mountain.
Photo by Ryan Linn
A rock with interesting striations sits in an alpine meadow.
Some neat striations in the rock on Parker Ridge.
Photo by Ryan Linn

I descended along Parker Ridge Trail, which has some more amazing views as well as some really astonishing geological features. On the way down, I passed a group of four folks hiking up to the Pond, one of whom gave me a tasty apple by way of greeting. Taking food from strangers? Don’t mind if I do!

I ended up back at my car by 2:30 PM, finishing the first of two major loops. The Little Jackson-Tumbledown Pond loop would be a fantastic day hike on its own. But I had other business.

Next up, I walked a mile and a half down the road to the Loop Trailhead. This was where I’d hiked during my previous trip to Tumbledown, and I knew it would be a rugged, difficult trip, especially starting so late in the day. After a fairly straightforward climb to the base of the cliffs of Tumbledown, the trail first jumps up 500 feet in a quarter mile, takes a break by walking along an exposed ridge, then climbs another 800 feet in 0.4 miles, before reaching the ridge of the mountain.

The temperature wasn’t much more than 60 degrees, but I was pouring sweat and aching all over by the time I got to the top.

A view from a ridge of distant mountains and lakes.
Back to Tumbledown Pond with  Little Jackson Mountain above.
Photo by Ryan Linn

Best of all, the last short climb to the top goes through one of the most entertainingly-named features I’ve seen on a trail– Fat Man’s Misery, a spot where you have to climb straight up through an overhead chimney, using iron rungs and squeezing through a tight opening in the rocks. It’s a funny name, but pretty apt. I’m a scrawny guy, and it was a tight squeeze even for me.

I ended the day by walking across the ridge of Tumbledown, with fine views across to the giant cliffs that make the mountain so spectacular. I got back to Tumbledown Pond around 5. By now the anglers had headed home, or to camp, but I was able to have a nice chat with a local lady and her very affectionate German Shepherd.

One of my favorite parts of this mountain is that the local area is so sparsely populated. Being able to meet a local who hikes the mountains gave me some great ideas for coming back in the winter, or just visiting other parts of the region.

In the end, I had to get moving to beat nightfall. I got to my car at 6:30, with a long two-hour drive ahead of me. The full tally for the day was 17.6 miles, 6800 feet of elevation gain, and 200% daily value of aches and soreness. I’m still aching a lot. It was absolutely worth it.

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Photo by Ryan Linn
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Photo by Ryan Linn
Get our hiking guide for this area!

Walk lush forest paths, rocky coastlines, and towering peaks on New England’s trails.

Ancient mountain ranges, deep forests, and thousands of miles of hiking trails await you when you hike in New England. Our hiking guides include Maine’s Baxter State Park, Public Reserved Lands, and Acadia National Park. Mighty peaks in Maine, such as Katahdin and the Bigelows, offer up dramatic views atop rugged climbs, while the coastal hills can be just as wild and beautiful. In our White Mountain National Forest hiking guides, you will find New Hampshire’s 48 Four-Thousand Footers, over a thousand miles of hiking trails, and endless possibilities for hiking adventures. The variety of New England trails in many more scenic destinations are perfect for thru-hiking, section-hiking, day-hiking, or backpacking.

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Acadia National Park
…and more!
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About the Author
A man wearing a backpack and carrying trekking poles stands on top of a rock cliff with a view behind him.

Ryan Linn

Ryan is also known as “Guthook”, which is where our apps get their name. Already an avid hiker, he hiked the Appalachian Trail, New England Trail, and Pacific Crest Trail before joining forces with Paul to create the Guthook Guides apps. Ryan handles iOS development for our apps from his office in Maine, and usually runs away to the forests and mountains throughout New England. He also volunteers with the Maine Appalachian Trail Club and the Natural Resources Council of Maine. Baxter State Park in Maine is his happy place.