Winter Hike East Osceola and Mt. Osceola

Greeley Ponds Trail SignHike Distance: 2.8 miles to East Osceola + 1 mile to Mt. Osceola (don’t forget to come back)
Time: 5-8 hours
Difficulty: Pack the Aleve
Elevation: East Osceola 4,156 feet; Mt. Osceola 4,340 feet
Recommended GearTrekking Poles with winter baskets and/or a Mountaineering AxeCrampons; Winter Hiking Boots or Mountaineering Boots; Alpine Snowshoes

Due to the Tripoli Road closure, a winter hike of East Osceola and Mt. Osceola is best done from the Kancamagus Highway trailhead for the Greeley Pond Trails. This route is only 2.8 miles to East Osceola, but there’s a catch: it’s incredibly steep. Be careful to check current trail conditions on New England Trail Conditions, Trails NH, or Views from the Top before assaulting this hike, because icy footing due to weather or butt sliders can be hazardous. In all winter conditions, big-boy crampons are the better option over microspikes for this hike. 

It was minus three degrees when I reluctantly opened my car door in the Greely Pond parking lot. You can probably feel it—the type of cold that’s undeterred by clothing, instantly stinging fingers and numbing thighs. Climbing a mountain in these conditions is to pee into the fierce wind of common sense, but I also didn’t want to waste a negotiated and planned hiking day. And since I was by myself—literally, no one else was in the parking lot—I told myself that the summit might not be in the cards.

This hike was going to be about making good decisions. The first was to get moving as quickly as possible. The 1.3 miles of hiking on the Greeley Ponds Trail trail is a gradual climb, weaving amongst hardwoods and conifers. The trail is typically well packed, and the only obstacle worth mentioning is a double-crossing on the South Fork of the Hancock Branch, which I found mostly bridged with ice. Along the way, there are numerous glimpses through the trees of the cliffs beneath Osceola’s northern spur.

South Fork Crossing
The South Fork of the Hancock Branch.
Mt Osceola Trail Sign
The junction of the Greeley Ponds Trail and the Mt. Osceola Trail.

The real hiking begins after turning onto the Mt. Osceola Trail. Having read recent trail reports that the climb consisted of packed snow, I switched to snowshoes at this junction to avoid post holing and take advantage of the heel bar on the steeper ascents. It isn’t long before the trail starts climbing at an angle beneath the cliffs with what I would categorize as normal steepness.

Osceola Trail Sunshine
Boy oh boy was I glad to see this guy show up.
Osceola Trail Boulder
There are several cool boulders to check out on the non-life-threatening section of the Osceola Trail.

And then the hike gets seriously bad-arse with several sections of hold-on-to-your-hat climbing. I found it manageable on the packed snow using my snowshoes with the heel bar engaged, but opting for crampons also wouldn’t be a bad decision. If you’re planning on doing this hike as your first ever winter trek, in the esteemed words of Mr. Ice Cube, you better “chick-ity-check yo self before you wreck yo self.” In all seriousness, work up to this hike by first conquering a hike such as the Hancocks on the other side of the street. You don’t want search and rescue to have a word to your mother. 

[Editorial note: apologies for the lame attempt at being cool.]

Osceola Trail Steep Winter Climb
Trail photos often don’t look as steep as the in-person view. That’s not the case here.

At one point the trail crosses an open slide. The wind began to make its presence felt here, and I had the distinct feeling that if I leaned back too far, I just might fall off the mountain. On this day, the bitter cold and merciless climbing had its rewards—a cloudless sky enabled the White Mountains to show off for my camera.

Osceola Trail Slide View Hancocks Carrigain
As viewed from the slide, the Hancocks are on the left with Mt. Carrigain on the right. The Presidential Range is photo bombing in the very back.
Osceola Trail Slide View Tripyramids
The Tripyramids are also visible from the slide.
Osceola Trail Slide
The upper part of the slide re-entering the trees.

Eventually, the trail reaches a shoulder on East Osceola, to the right of which is an outlook with views of Mt. Osceola and the mountains of Franconia Ridge.

Mt Osceola
Mt. Osceola as viewed from the shoulder of East Osceola.

While still within treeline, the ridge approach to the East Osceola summit is more exposed to the high mountain winds. I found myself layering up sooner than I planned. The trail through this stretch alternates between steep climbs and somewhat flat sections. Before beginning the last climb to the summit, there’s another viewpoint on the left. In the summer, the views are limited by the trees below, but several feet of snow to stand on certainly does an outlook good.

East Osceola Outlook
Approaching the outlook beneath the East Osceola summit.

East Osceola Summit Approach
I believe this was the final climb to the East Osceola summit.

The East Osceola summit is unremarkable, a small cairn within the trees. I missed it on the first pass. From the East summit, the trail descends several steep sections to the col between the two mountains. On the way down, there’s one good vantage point with views of Franconia Ridge.

East Osceola View Franconia Ridge
Mounts Flume, Liberty, Little Haystack, Lincoln, and Lafayette, comprising the Franconia Ridge.
Osceola Trail Chimney
Just above the col is Mt. Osceola’s notorious chimney, a steep rock ledge that gains a coat of ice in the winter. Quite simply, there was no way I was foolish enough to attempt this by myself.
Osceola Trail Chimney Alternative
To the right of the chimney is an alternative route that wasn’t looking much better.

It was decision-making time. With crampons and my mountaineering axe, I was confident I could climb the alternate route. But what if I fell? In the few seconds I’d taken to ponder the situation, the gnawing cold had already returned pain to my fingertips. An injury here was guaranteed hypothermia. But there was even more at stake. What many people don’t realize is that when you take risks in the backcountry, you’re not only putting yourself in danger, you’re also jeopardizing the search and rescue team members. Solo climbing this section in sub-zero temperatures would have been negligent. 

While telling myself that I had to turn around, I noticed a snowshoe track breaking off the trail. An alternate route to the alternate route, perhaps? It was worth investigating, and sure enough, I was in luck. Before I knew it, I was safely above the chimney and continuing on my merry way. The sudden change of events put an extra pep in my step as I scrambled up the last of the steep slopes and basked in the summit sun. 

Osceola Trail Tree Tunnel
The tunnel of mountain love.
Osceola Trail Summit Call
The summit is waiting. Will you answer the call?

Mt Osceola Summit
The Mt. Osceola summit dressed in its winter coat.
Mt Osceola Summit View East Osceola
The view of East Osceola from the main summit.
Mt Osceola Summit View Waterville Valley
Looking over Waterville Valley.

Mt Osceola Summit View Mt Washington
Mt. Washington from the Osceola summit.
Posted in
New Hampshire, New Hampshire Trail Reviews, Pack the Aleve
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6 responses to Winter Hike East Osceola and Mt. Osceola
  1. Long Lin says:

    Hey dude, awsome review. I’m thinking about going up to this mountain this weekend. bringing someone along with me that might not be as comfortable as me on the moutnains. any chance you can give me a bit more detail on the alternative rount you took up the Chimney?

  2. Slorunnr says:

    did this on saturday, it was labeled as an “intermediate” hike by the hike organizer. I have been hiking for over ten years, novice, intermediate and advanced summits. This was no intermediate hike. The descent was treacherous. I wouldnt recommend this to anyone who doesnt have crampons and axe or experience.

  3. Shane D says:

    Love the photography work that came with your hike review. Finding a good winter hike can definitely be a little bit of a task. Out of curiosity I’m seeing the comment about this being above an intermediate hike, are there any particular winter hikes you would recommend for beginners who are relatively new to the area but are still worth doing? Curious where you would point to someone just starting out. Thanks!

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