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Hiking East Osceola and Mt Osceola in December

Hiking the Osceolas in December

East Osceola (4156′) and Mt Osceola (4340′) are two more 4000 footers where the winter route is significantly more difficult than the summer route. The easier, southern, three-season route starts at Tripoli Rd in Waterville Valley and the ascent is relatively gradual. But Tripoli Rd is gated closed in winter, so you have to climb the peaks from the north side where the ascent is a grueling, steep climb up several very steep pitches that can be quite icy in winter.

I knew all this before I set off on this hike, because I’ve climbed these peaks before in winter, several times in fact, and because I enjoy the process of planning my hikes in order to prepare for them. But I’d never climbed them in December before and needed to summit them for my White Mountains 4000 footer grid.

Ridgeline walk to Mt Osceola from East Osceola
Ridgeline walk to Mt Osceola from East Osceola

What I couldn’t foresee was what the trail conditions leading to these two peaks would be like, in part because no one had climbed them recently and written a trip report about it on This is an online bulletin board where hikers share trail information about snow conditions, water crossings, trail hazards, and trail maintenance needs. It’s very useful for deciding what gear to bring on winter hikes, particularly in terms of traction aids.

In the absence of good beta, I packed a pair of Hillsound Trail Crampons (microspikes) and a pair of Hillsound Trail Crampon Pros (crampons), my ice axe, and old rain pants, because I anticipated having to climb up an icy trail, but wanted the option to glissade down on my butt, using my ice axe as a brake.

In hindsight, I would have probably been better off with an even more aggressive pair of crampons, because the trail was covered by 8-12″ of very fine dry snow the consistency of flour. This made it hard to get a good bite into the ice below the snow because the spikes on the Hillsound Pros weren’t quite long enough and floated on top of it. I still managed to claw my way up to East Osceola and then Mt Osceola after that, but a crampon with longer spikes, like my CAMP XLC 490 crampons would have probably made the effort much more efficient.

View of East Osceola from the summit of Mt Osceola
View of East Osceola from the summit of Mt Osceola

I got to the Greeley Pond Trailhead at 8:30 am and bare-booted up the Greeley Pond Trail to the Mt Osceola Trail junction. From there I continued to bare-boot to 3000′ relying on my boot treads for traction. I stopped here and put on my crampons for the ascent up to 3800′ where the gradient to the East Osceola summit becomes a bit more manageable. That 800′ climb is only about 0.3 miles in length and it is pretty much straight up. It was slow going, but you just keep on going until it gets easier.

The snow at 3800′ was pretty deep from drifting, but I plowed ahead because it was just another 300 feet to the summit which is marked by a pile of stones, barely big enough to call a cairn. From there I dropped into the col between the peaks where there’s a chimney you can climb or bypass to continue up the trail to the main peak. The chimney was full of ice, so I took the bypass, which wasn’t a cakewalk either, chopping my ice axe pick into the ice in order to pull myself up. From there it was another slog through loose powder up the ridge to the main peak and its outlook.

After a sandwich and a drink, I pulled on my old pair of rain pants, so I could glissade portions of the ridgeline trail back to the chimney and the bypass. I descended the bypass much the same way as I climbed it, chopping my axe into the ice so I had something to hang onto as I backed down the ledges to the bottom of the col. From there, the climb back up to East Osceola summit went surprisingly smoothly, probably because the calories from my lunch peanut butter and honey sandwich were kicking in.

Ridgeline walk from Mt Osceola to East Osceola
Ridgeline walk from Mt Osceola to East Osceola

I started glissading down East Osceola but found it difficult to brake very effectively with my ice axe in the slippery snow. The trail is bordered by trees, so an uncontrolled descent could end very badly. So I gingerly sidestepped my way downhill bracing myself with my axe uphill and occasionally glissaded short sections when it was too steep to descend any other way. Once down to 3000 feet, I removed my crampons and rain pants and bare-booted back to the trailhead.

This was a tough hike, but the Osceolas are always tough in winter. Since I also need them for January, I have a feeling I’ll have another crack at them all too soon.

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  1. These trip reports are fantastic! I’m still working through the 48 but I like winter hiking as well, so I’m not “saving” them for better weather. Knowing what to expect in advance is great-and your reports are much more detailed than the NETC reports. Obviously those will be more current, but the information about trailhead approaches, etc. is what I’m really after. Hope to bump into you out there some time-and thanks for your work on this site!

    • My first round of the 48 had a few winter peaks on it too. You really get to see the bones of the mountains when the leaves have fallen. And there are a lot fewer people out there cluttering up the trails.

  2. Good idea to bring your axe as there is that one dicey spot near the top of East that has serious exposure. Was up there in March 2019 and fell in a spruce trap 3 feet off the rail on top of E. Wrenched a knee and was lucky to have help getting out, but was worried we both might end up in the trap trying to get out. We ascended in spikes but switched to full crampons for the descent which was the right choice. Should have switched going up but sometimes you think the hassle isn’t worth it and you’ll be through it soon enough. On the last brook crossing 1/4 mile from the Kanc the knee gave out stepping up the far bank and splash! ended up laying on the pack in the icy brook with water pouring over shoulders an couldn’t get up with pack snagged on rocks. Once again, glad to have help even if the help was laughing hysterically! A memorable day…

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