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summit view from owlshead cherry mountain

Butt-Sliding on Cherry Mountain (aka Owlshead)

Posted on January 5, 2026January 5, 2026

The first hour took an hour. The second hour took two. And the third hour took about twenty minutes. At least, that’s how it felt going up and down Cherry Mountain on Saturday.

After a solid holiday week of skiing and sledding with a ton of family and friends, I finished vacation off with “a little zen” in the mountains. That’s what my wife called it anyway. And you know what, it almost always is. The chance to stretch my legs and go exploring never fails to bring me some level of peace that I was lacking before I headed out.

owlshead trail
smiley face cherry mountain

Cherry Mountain

Cherry Mountain is a little confusing name-wise because there are two peaks on it, neither of which indicate the name Cherry. One peak is called Mount Martha, most likely named for Martha Washington, and the other is called Owlshead — not to be confused with the 4000-footer named Owl’s Head.

Cherry Mountain’s Owlshead is on the 52 With a View peak list, where it only recently replaced the aforementioned Mount Martha. It was determined by the governing powers of the list that Owlshead offers better views when you are roaming the collective region known as a Cherry Mountain, so Martha got the axe.

Mount Martha

Sorry, Martha.

Searching for Views

I’ll have to check out Mount Martha someday, though, to see if I agree, because Owlshead is the first peak on the 52WAV list that didn’t blow me away with its view. It could be that it was a very gray day and the surrounding range was obscured by a haze of mist, but on every other climb of these peaks, even on Paugus which was a trail I loathed, I always got to the top and felt myself thinking, “Oh wow.” Or something to that effect.

But on Owlshead, not so much. In fact, I almost missed the views entirely. When I reached the summit, there was a sliver through the trees where you could see the surrounding valley, but it was limited. Following the GPS tracks of another climber, I decided to go beyond the summit, towards Mount Martha, and was so glad I did. About fifteen feet below the summit is a little ledge that allows you to take in the breadth of the neighboring mountains and Walker Valley. From this spot, Martha stands a few hundred feet above you to the right. A knobby-looking peak called The Humps, sits to its left.

the humps nh

The Humps. On a clear day, the Presidentials can be seen in the distance, but not this day.

Rewards Always Come

It’s a good view, don’t get me wrong. Maybe even a great one on a clear day—I’ve seen others’ pictures of the Presidentials from there, and the images are pretty spectacular. But on this day, it felt a little lacking for the spirit of the climb. I labored through a winter wonderland of snow-draped spruce and fir to get there, and the magic of the hike made me expect something truly special at the summit.

The ascent was surprisingly difficult given that it was just a little over four miles round-trip. With some very steep sections near the top, and some large snowdrifts to contend with, I had to crawl on my hands and knees several times. I don’t think I’ve had to do that since the Hancocks many years ago. It made me regret leaving my hiking poles and my ice axe in the truck.

The top of Owlshead is a sharp cone, and the effort up felt deserving of a solid reward, but maybe I was spoiled since I had just spent the week in the mountains. With all of the hiking I’ve been doing lately, maybe my expectations are out of whack. There was one delightful reward, though, from the steep ascent: a chance to butt-slide down at least a quarter mile of trail. That’s why the last hour felt fast — and maybe it was. The total hike took me three hours and fourteen minutes, and the descent felt like nothing. When I wasn’t butt-sliding, I was lumbering down at a jogger’s pace, snowshoes and all, and made great time.

owlshead aka cherry mountain

Conehead

The Beauty of Winter Hiking

One of the things I love about hiking a mountain like this in winter, when you don’t necessarily get the greatest views at the summit, is you still have a remarkably beautiful hike throughout, and you didn’t waste a summer day to do it. I felt this way about a recent climb to Middle Carter as well. When the views are less than extraordinary, but you still want to check out a new route to climb, winter hiking assures you of a beautiful adventure regardless of what you see at the top.

Perhaps though, I’m judging Owlshead too harshly. I’m back in the low country now, and maybe that’s just what I need to hit the reset button and make every mountain view spectacular again. I suppose that’s one benefit of living away from the mountains that I’ve been forgetting. That without getting a significant change in perspective each week, mountains lose their grandeur. In fact, when I first pulled up to the trailhead and saw Owlshead, which stands over 3200 feet, it looked small to me. A few days of driving around southern New Hampshire should correct that.

mount martha

Next time: Mount Martha

Field Notes

camper in the woods
  1. Sometimes when you are out in the woods, you run into some strange stuff, and this hike had its share of peculiar sights. An abandoned camper certainly carried a spook-factor in the early going. I also spotted some torn caution tape, dangling from some trees. The combination of the two made me think I had stumbled upon a crime scene where a murder took place. Or was about to happen!

2. For the descent, I wished I had an ice axe or hiking poles. Actually, hiking poles would have been very helpful on the way up as well. But on the descent, some of the butt-sliding sections were steep and fast, and having an ice axe would have been a welcome safety measure. The snowshoes helped slow me down a bit, but I could have used some more help.

butt-sliding cherry mountain
owlshead in the mist

3. Someone rerouted the original Owlshead Trail at some point. My internet research suggests about fifteen years ago, but I didn’t dig too deeply into it. But you can see in the foreground of the picture to the left, at the base of the mountain, a small structure. I spotted a couple of them out there. It appears to be private land with its own road leading up to it, and a closed gate to boot. Clearly, hikers should keep away. Respect their wishes.

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