“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.”
-from 4000s by 40
This page shares photos from Chapter 18 of 4000s by 40. Osceola turned out to be one of my favorite 4000-footers, both for its shorter distance and excellent views. If you’re climbing the 4000-footers and want to know more about what it’s like to take them on, you can get the book [here]. And to go along with the photos below, I’ve added a quick retelling of events, along with quotes, to give a small sense of what you’ll find in the book. Enjoy!
The Mount Osceola Trail
By the time I finally got my chance to climb Osceola, I was frustrated. Three times I had tried 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 season when I arrived at Tripoli Road. So my mind wasn’t quite right when I pulled into the Mount Osceola trailhead—I wanted to crush Osceola like a bug. Given the relatively short distance to the summit, I ditched the backpack, donned running sneakers, and flew up the mountain faster than any climb I’ve done before or since.
It’s about 3.2 miles to the summit, and I arrived in roughly an hour. I didn’t know it before this first ascent, but the climb up Osceola—despite being a tough trail of angled rock—runs faster than most of the other 4000-footers. At least, I think it does. But I was also running it, so my gauge might be off.
Beautiful Summit of Mount Osceola
“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
Usually, I like to linger on a trail so I can be present. But ironically, I felt very present on this hike. Maybe it’s because I didn’t take many pictures. I ran with a small exercise belt that held my phone and a couple of snacks, but I didn’t pull it out until I reached the summit. Despite the quick pace, I was able to focus on my surroundings, and I 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 many photos to go along with it.
If you look to the far right in the photo below, you can see Waterville Valley’s ski trails in the distance. Mount Osceola’s summit is open and broad, offering a highly rewarding view for what I regard as the least amount of effort required as far as 4000-footers go (Mount Tom is an easier climb, but the views aren’t nearly as good). The 52 With a View list gives you a similar type of reward for the effort. If you’d like to see more photos of Mount Osceola beyond this climb, 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 felt a little silly for having taken on Osceola in such a frantic way, but on the drive home I realized I no longer really cared about the 4000-footer list. I just liked being in the great outdoors, and the list was simply a guide to get me there. Climbing helps me reset so I can be a better person. It helps me 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, I want to feel that I was more of a help than a hurt to this planet and to 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.”
Climbing Through Life
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.
🧭 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.