“Even if I was hiking at a leisurely pace, it would have been tricky to keep my feet, but I was angry at this mountain, so I was running it.”
By the time I finally got my chance to climb Osceola, I was frustrated. Three times I had tried to climb it before, and three times my plans were thwarted. Once because of poor planning, forgetting to bring spikes on a winter hike, and twice because the trail I wanted was still closed for the winter when I arrived at the Tripoli Road. Given the relatively shorter distance to summit Osceola, I ditched the backpack, donned running sneakers, and flew up the mountain faster than any climb I’ve done before or since.
The Mount Osceola Trail
It’s 3.2 miles or so to the summit, and I arrived in about an hour’s time. I didn’t know it before this first ascent, but the climb up Osceola, despite being a difficult trail of angled rock, runs faster than any of the other 4000-foot trails. At least, I think it does. But I was also running it, so my gauge might be off.
Usually, I like to take more time on a trail so I can be present, but ironically, I found myself very present for this hike. Maybe it’s because I didn’t really take any pictures. I ran with a little exercise belt that allowed me to carry my phone and a couple of snacks, but I didn’t stop to pull out my phone until I reached the summit. Despite the quick pace, I found myself able to focus on my surroundings and can picture most of that climb clearly in my memory—probably more so than any other climb I made that year. I just don’t have a lot of pictures to go along with it.
“Osceola showed me that being present is possible while moving fast, as long as you eliminate your distractions and focus fully on the moment.”
Mount Osceola’s Summit
If you look to the far right in the picture above, you can see Waterville Valley’s ski trails in the distance. Mount Osceola’s summit is open and wide and gives you a highly rewarding view for what I regard as the least amount of effort required for a 4000-footer summit. The 52-with-a-view list gives you a similar type of view reward for the effort. If you’re looking for more pictures of Mount Osceola, beyond this particular journey, you can check out some of my other posts like this one, or head over to wanderingmatt8 on Instagram where I share my love of these mountains and other outdoor adventures.
Reflections from Mount Osceola
Maybe it was because I was feeling a little silly for having taken on Osceola in such a frantic way, but I started reflecting on the way home and realized that I no longer really cared about the 4000-footer list. I just liked being in the great outdoors and the list was really just a guide to get me out there. Climbing helps me reset myself so I can be a better person. It helps me better handle the ups and downs of regular life, and approach others with more charity and patience. More kindness. And that’s what it’s all about right? When I look back on it all, I want to be able to feel that I was more of a help than a hurt to this planet and the people I know. Mountains help me with that.
“When I leave this life, I want it to be with as many positive feelings as possible, because in the end, that is the great aggregate; that is the great accumulation of wealth that one can ever hope to achieve. Not how many points you scored against others, but how many points you helped others score. That’s the only tally that matters.”
🧭 Ascent Details: Mount Osceola (4,340′)
Route: Mount Osceola Trail from Tripoli Road
Distance: 6.4 miles round trip
Elevation Gain: ~2,050 feet
Trailhead Location: Tripoli Road (seasonal access, typically open late May–October)
Difficulty: Moderate
Trail Features: Gradual switchbacks, rocky footing, partial ledges near summit
Summit: Open summit with excellent views of the Sandwich Range and southern Whites
Notes: This route is one of the more accessible 4000-footers. Can be icy or muddy in shoulder seasons due to snowmelt. No water sources—carry your own.
Exploring Mount Osceola: Trail Reports & Peakbagging Resources
Osceola is a great 4000-footer. The views are some of the best you can get in New Hampshire, and I’ve never had a day where I wished I chose another mountain when I’ve stood at Osceola’s summit. If you’re looking to go, here are a few key resources to help:
- Peakbagger.com – Mount Osceola | – A great place to track your 4000-footer progress, log summits, and see detailed elevation data.
- NewEnglandWaterfalls.com – Provides difficulty ratings and highlights scenic viewpoints in the winter—I wish I had known about this website when I first tried to tackle the Osceolas in the winter.
- AMC Trail Maps – I have different versions that came with a more detailed trail book, but it’s always good to have a reliable map.
Want more?
If you like reading about mountains, the 4000-footers, and the ups and downs of getting “out there,” come check out more stories at 4000s by 40.
Looking for photos of more 4000-footers? Head back to the 4000s by 40 Visual Companion to explore the other peaks.