Osceolas in Winter

Osceolas in Winter

Hike Date: February 7, 2021

A cold but perfectly clear and windless day on East Osceola and Mount Osceola in the White Mountains of New Hampshire.


0 ft
Elevation Gain


Segment Distance

Total Distance

Route Description

0 mi0 miStart at Greeley Ponds Ski Trailhead (just west of Greeley Pond Trailhead)
0.8 mi0.8 miLogging trail to Greeley Ponds Trail
0.5 mi1.3 miGreeley Ponds Trail to Mt. Osceola Trail
1.5 mi2.8 miMt. Osceola Trail to the summit of East Osceola
1 mi3.8 miMt. Osceola Trail to the summit of Mt. Osceola
1 mi4.8 miMt. Osceola Trail back to the summit of East Osceola
1.5 mi6.3 miMt. Osceola Trail back to Greely Ponds Trail
1.4 mi7.7 miGreeley Ponds Ski Trail back to parking


Note: Map mileage does not match stats because Gaia GPS tends to undercount it. Mileage stats were calculated using the White Mountain Guide and Trail Maps.

You know those days when so many things don’t go as planned? Well, this was one of them! Naively thinking that trailheads wouldn’t be that busy, we got a later start than usual to sleep in just a bit. We got to the trailhead around 10am and the tiny parking lot was completely full – only 3 vehicles fit in the unplowed space. Even the nearby roadside pull offs were full. We drove around a bit, looking for another trailhead with room, and everywhere was completely packed or snowed in.

Resigned to not hiking a 4,000 footer, we decided to drive back past the Osceolas and park on the side of the Kancamagus Highway at a cross-country ski/snowshoe trailhead to snowshoe through a flat section since none of our plans worked out. At least we would get some time in the snowy woods on a beautiful day. But, when we got on trail and looked at a map more closely, we realized that the cross-country ski/snowshoe trail that we parked at actually met up with Mt. Osceola Trail! How serendipitous. We went from planning to hike the Osceolas, to not, to hiking another mountain in the area, to not, to snowshoeing around flat terrain, to not, to hiking the Osceola’s via a route we hadn’t heard of before. This whirlwind of a morning made us start hiking much later than we planned for. Also, all the changes in plans definitely threw off our moods for the first part of the day. Hiking, particularly in winter, absolutely relies on mental fortitude and it took a little bit of time for us to get into a flow and really appreciate being outdoors.

We put on our snowshoes and headed up the logging trail, which parallels Greeley Ponds Trail, towards Mt. Osceola trail. It was a beautiful route, and one that was definitely not well-traveled. We followed a lone set of tracks that stopped at a fallen tree across the path. We had to navigate off trail to find ways around a few of those and a swampy stream area. It was a gorgeous walk in the woods, but took longer than expected because of all the detours. We turned right on Greeley Ponds Trail, which was completely packed down from previous hikers, being the more typical route. Then, at the next trail juncture, we joined Mt. Osceola Trail, and enjoyed about a half to three-quarters of a mile of relatively gradual terrain.

Greeley Ponds ski and snowshoe trailhead
Beautiful winter trail on a sunny day

Then, the climbing began. This hike is relatively short and super steep! Don’t underestimate its difficulty. After a tough morning, this steep section felt like it took forever. I had to take my hat and gloves off and on to regulate my temperature and it was really challenging to get into a state of flow. To make it more difficult, the snow was scraped off of multiple parts of the trail due to people butt sliding down. This exposed icy patches, rocks, and smoothed out most of the trail into a scoured luge run. Slipping a lot and using every muscle to stabilize ourselves, we moved very slowly up to a viewpoint close to the summit.

Beginning of the steep climb

For maybe the second time of all of our winter hiking experiences, the sun was shining, the wind was nonexistent, and we were able to just sit, take in the beauty of nature, and relax on a winter day. Looking out from a viewpoint just before the summit of East Osceola, seeing the blue sky, and the mountains in the distance, I was reminded of why we push through some of the hard parts of the trail. We couldn’t have asked for a better day in the mountains and it was time to savor it.

Viewpoint just before the summit of East Osceola

The summit area East Osceola is small and relatively underwhelming, with just a cutout of trees to offer a small view. After a brief pause, following the trend, we butt slid down much of the descent into the col between the peaks. Then, we came to the chimney, an incredibly steep section of trail towards Mt. Osceola. There is a bypass to the right that is a little easier and less steep. On this day, we decided to take the bypass of the bypass, bushwhacking through the trees even further to the right following paths that other hikers had made organically.

East Osceola summit area
Hiking in the col between peaks
"The Chimney" area

After that, the trail steadily climbed, flattened out again, then climbed again for the last push to the summit. We could see the sun shining brightly in front of us as we emerged onto the open summit of Mt. Osceola, boasting expansive views. The sky was perfectly clear and we could see Mount Washington in the distance, shining bright white covered in snow and ice under the glaring sun. It was truly a special kind of winter day in the mountains.

Final stretch to Mt. Osceola
Mt. Washington in the distance
Expansive view from Mt. Osceola

On our way back to East Osceola, we alternated between walking quickly and butt sliding. We carefully climbed down the chimney bypass and made the ascent to East Osceola in relatively good time. We paused on that ascent to take in the views toward the Pemigewasset Wilderness from a small overlook. It’s another great viewpoint along this route and we enjoyed seeing the landscape that we have traversed in previous year on our 2 day and single day Pemi Loops.

View of the Pemi Wilderness and Mt. Washington

Hiking down the steep sections was really nerve-wracking. We had to take extremely careful steps to prevent ourselves from falling or sliding. Again, we alternated between butt sliding and stepping carefully. When we got to the Greeley Pond trail juncture, we opted to take the blue cross-country ski and snowshoe trail to the road. This trail was more travelled and easier to navigate than the logging road we came in on. With the sun going down, the temperature dropped as we hiked out in the late afternoon. When we made it to the road, we couldn’t believe what a day we had! We were tired but really grateful that we had the opportunity to hike the Osceolas. 23 of the winter NH 4,000 footers down, and 25 to go.

Cross country ski and snowshoe trail
Greeley Ponds cross country ski trails map

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