A couple of weeks ago, when I finished 4000s by 40 and it was finally published, I decided I needed to celebrate. But where does one go to celebrate after writing a book about climbing the 4000-footers in New Hampshire? Hmm, let me think… back to the mountains, of course!
Initially, I considered tackling Moosilauke, which gave me fits when I first set out on my midlife mission all those moons ago. It felt like a return to the mountain that got me started would be an appropriate way to celebrate. But then I remembered the Osceolas. I preferred the views from the Osceolas and recalled thinking how much I’d like to visit their peaks again. With fall foliage speeding up, I also thought the Osceolas would provide some better colors to feast our eyes on than Moosilauke. Moosilauke’s large, rocky expanse at the summit limits some of the fall colors you can drink in at this time of year. Since a friend was joining me for the hike, and it was his first time climbing a 4000-footer, I opted for where I thought I could get him better colors and better views.
We lucked out. It wasn’t peak foliage, but the birches and aspen were popping with yellow in the valley below. Moving at a decent clip, we made it to East Osceola in about two hours—maybe a little more. No ice on the ground definitely helped. The first time I climbed East Osceola, it was winter, and I almost didn’t summit. I’d forgotten spikes and had to hoist myself up through the brush and bramble. Continuing to Osceola “proper” wasn’t even an option—between the ice and the chimney, it would’ve been reckless. The chimney is a little rock wall, twenty or thirty feet high. It doesn’t require ropes, but if it’s icy and you’re unprepared, you’re not making it. This time, though—on East Osceola with good weather and a good hiking buddy—I was excited to finally check it out.
Climbing “The Chimney” On Mount Osceola

The “Chimney” between East Osceola and Osceola
The chimney is fun. It can prove too difficult for some, in which case there is a bypass to get around it, but in truth, the bypass isn’t much easier. If you’re up for a challenge, doing a little hand-over-hand climbing adds to the excitement of climbing Osceola, and I certainly recommend giving it a try if you can—especially because the views from Osceola are even better than what you get on East Osceola.
I don’t know why, but it’s only recently that I’ve started thinking about which 4000-footers are my favorites. I’ve always known which ones are among my least favorite, like Hale, but as I return to the mountains and decide which ones I’d like to see again, the cream is starting to rise to the top. Osceola and East Osceola are two of the good ones. The view from Osceola always reminds me of the views you get from Mount Bond, which is also a favorite but requires a heck of a lot more work—some twenty miles of hiking. My friend and I climbed both East Osceola and Osceola “proper” in about six hours; a good day’s work without having to go for something as hard to reach as Mount Bond. It was a great way to celebrate.
🗻 Ascent Details for East Osceola and Mount Osceola
- Route: Out-and-back via Greeley Ponds Trail and Mt. Osceola Trail
- Summits: East Osceola (4,156′) and Mount Osceola (4,340′)
- Mileage: ~7.6 miles round-trip
- Elevation Gain: ~3,150 feet
- Highlights: Steep ascent up East Osceola, scrambly chimney between peaks (with a bypass), panoramic views from Osceola’s open summit
- Trailhead: Greeley Ponds Trailhead on the Kancamagus Highway (Route 112)
- Notable: Chimney section can be tricky—especially in wet or icy conditions—but there’s an easier bypass to the right.
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