Originally written and posted January 14th, 2023 at 11:21am.
Hike Type: Out-and-Back
Distance: 8.3 miles
Elevation: 2851 feet
Time: N/A
Hiking Challenges: New Hampshire 4000 Footers
The Hike
Gen and I had such an incredible time climbing Mt. Moosilauke, we headed back up to the whites only two weeks later to tackle the next 4000 footers! We found an article of the "6 beginner 4k hikes" or something, so we decided we would work on that list (which in hindsight, we did a good job with, until our fourth hike was the Hale-Zealand-Bonds traverse... whoops!) which brought us to the Osceolas! We slept at Gen's family cottage in Raymond, NH the night before and left around 4am to hit the trailhead just after sunrise. Emma drove down from northern Vermont, and we were shocked to find her only a few minutes behind us! The trailhead had my favorite thing in the world - composting toilets - so we made use of those, got suited up on the chilly 32-degree morning, and got to our hike!
The trail started out incredibly gentle before beginning to climb. This day ended up being an experiment of layering - and I'm just now remembering that I was hiking this in my old sneakers and cotton sweatpants. We were definitely cold at first, but after the first 20-ish minutes we de-layered because we were cooking. Another 30-ish minutes went by and we were suddenly freezing again (partly because we were wet with improper gear, partly because the wind picked up), so we re-layered. We eventually reached an equilibrium, thankfully, but not without consequence (Gen got a great shot of my ass sweat later in the day).
The trail itself was rather forving with moderate grades and switchbacks galore. Every now and then we would find the sun peeking through the trees which was lovely. In the upper half, there were plenty of switchbacks that eased the grade, but many were along slanted slabs that were brutal on my weak, unprotected ankles. It was in this upper half we also ran into some backpackers who spent the night somewhere in the woods, and were headed back down.
The trail calmed down near the summit with numerous side paths that I did not know about (I didn't get the White Mountain Guide until a few months after this hike), so we continued on to the main view which was spectacular! It was only us and one other person this early in the morning, and the sun was just high enough to warm us back up in the wide open area. We had snacks, took photos, and rested for a while, before continuing our journey onward to East Osceola.
In hindsight, this is where the trail became more of a classic "white mountains hike" - right down and then right back up again, no funny business. There were some nice views toward East Osceola and the surroundings heading down Osceola, and just a bit of autumn red in the valleys. When we hit the fabled chimney section, a group of oncoming hikers told us to veer left to do the bypass on the way down - thank goodness we passed them or else we would have had a whole time getting down that chimney.
The final push up East Osceola was moderate and straightforward, with one great peekaboo view of Mt. Washington and nearby peaks. The actual summit of East Osceola is wooded and underwhelming, with a cairn and a sitting log. We took our pictures, had a snack, and then started retracing our steps.
The entirety of the return trip was swimming upstream. You could tell this was a popular white mountain hike - we passed at least 100 people, if not more. Going up the chimney was very fun and not scary at all, and the final push back up Osceola got a little steep. The main view of Osceola was now a mad house with at least 30 people - we tried to take a break but got way too cranky. The final descent was more of the same - swimming upstream. I know uphill hikers get the right of way, but after a while we just started pushing on. We did pass one couple that was arguing about the hike which was fun! We also got complimented on our matching cotopaxi gear... 14 times. By the end of the hike our knees and ankles were hurting from the descent, but it was still an amazing hike and definitely one of the better "intro to 4k" hikes. We ended our day at the Woodstock Inn Brewery where I had the best margarita before making the pilgrimage home.
*a note I just remmebered - this was 2020 so EVERYONE was getting outside to hike, and there was the weird combination of maskless hikers, hikers with gaiters, hikers with masks, hikers who would jump into the woods to keep 6-ft, and my favorite, the ones who would stop and stare into a tree to avoid breathing on somebody.
"Mt Osceola Trail" from White Mountain Guide, 30th Edition (2017)
The trail leaves Tripoli Rd. and climbs moderately with rocky footing, going east across the south slopes of Breadtray Ridge and crossing several small brooks. At 1.2 mi., the trail begins to climb by switchbacks toward the ridge top, and the footing improves, although there are still occasional rough sections. At 2.1 mi., the trail swings right across a small brook (unreliable). The trail resumes its switchbacks, crossing numerous angled slabs that may be icy in cold seasons and passing a view southwest. It gains the summit ridge and turns right, and soon crosses a ledge at 2.9 mi. at the site of an older fire tower site (probably the true summit); here, a side path leads 20 yd. left to a ledge with a good view north. In another 50 yd., the trail reaches the large, open, east-facing ledge at the more recent fire tower site, with excellent views. The trail then turns left and descends from the summit, alternating easy stretches with steep, rocky descents.
Just before reaching the main col between Mt. Osceola and East Osceola, the trail descends a steep chimney (easier to climb than descend), which can be avoided by a somewhat less difficult but still tricky detour to the left (north). (Just above the chimney is a view of East Osceola). The trail crosses the col at 3.5 mi. and climbs moderately with steep pitches past a fine outlook on the left at 3.7 mi., reaching the wooded summit of East Osceola (marked by a small cairn) at 3.9 mi. [...].
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