Mount Osceola and East Osceola Hike with the Chimney
Mount Osceola and East Osceola, commonly referred to as “The Osceolas”, are an extremely fun day hike in New Hampshire! I hiked this trail with my friends one summer and we had an absolute blast. The views on Mount Osceola are jaw dropping amazing and can be reached by a fairly short day hike.
Continuing on to East Osceola is of course optional. However, for anyone working on the NH48, it’s a must! I highly recommend continuing on because it lets you see more of the trail, gives you a short rock scramble, and you’ll get there in no time!
Keep reading this post for more information on hiking Mount Osceola and East Osceola.
As of March 2025, for others of the 48 4,000 footers, I have posts on Tecumseh, Tom/Field/Willey, and Pierce as well. There are more posts to browse on my Hiking Page (as well as links to all my favorite hiking and camping gear and snacks!) and in my New Hampshire Posts Section as well.
- Parking and Trailhead
- Busy Busy Busy
- Alternate Trailhead
- Trail to Mount Osceola
- Trail Stats
- A Must-Stop-for-a-Snack Summit
- Hiking to East Osceola
- The Chimney
- Wooded Summit
Mount Osceola Parking and Trailhead
To hike Mount Osceola, you will likely want to drive to the trailhead on Tripoli Road. This road is closed in the winter, so keep that in mind when planning your hike. Additionally, even in the summer the road can be rough for some vehicles as it is not paved. The dirt, rocks and potholes can do some damage depending on recent conditions.
At the trailhead, there is a small parking lot that asks for the $5 parking fee commonly seen in popular areas of the White Mountains National Forest. If you don’t know the parking situation at a trailhead, as a good rule of thumb, always carry some $5 bills with you! Another great feature about this trailhead, again due to its popularity, is that there are two toilets.
There is a clear trail sign as well. The trail sign and Mount Osceola Trail start at the back left corner of the lot (bathrooms on your left and fee sign on your right).
Busy Busy Busy
Since the parking lot is fairly small (holds 15 cars or so), it will fill up quickly in the busy hiking season. If you want a parking spot, be sure to arrive early. However, since the trailhead isn’t on a main road, parking is available along Tripoli Road for those coming later which is nice.
My friends and I pulled into the last spot in the parking lot when we arrived just after 7am on a Saturday in late July. By the time we finished our hike, the lot was absolutely packed! There were still people trying to enter to look for a spot with no luck.
Driving away, we could see Tripoli Road lined with dozens of cars in either direction. We had come up to the trailhead from the southeastern side of Tripoli Road. As I mentioned, that route was very pitted and rough.
As we left though, we decided to go right out of the parking lot, towards Lincoln. Though the drive was longer, the road conditions were much better this way. Along this portion of the road we passed a ton of campgrounds and the Tecumseh trailhead. Cars were parked along the roads and campsites were set up further in the woods.
(Note that while Mount Tecumseh is another 4,000 footer that can be hiked from Tripoli Road, it is commonly hiked from the Waterville Valley ski area. My post on Mount Tecumseh focuses on the Waterville Valley trailhead.)
I was unfamiliar with rules for camping on this road but it looked like such a fun time and of course it was in a great location! After some searching, I found info on the WMNF website which shares the following:
- Take exit 31 off I-93 and drive 2 miles down Tripoli Road to the registration trailer
- $25/night mid-May-October
Alternate Trailhead
Mount Osceola Trail (which is what this post focuses on) does go past East Osceola and eventually hook up with Greeley Ponds Trail. That trail continues to Route 112 in New Hampshire (the Kancamagus Highway). So if you wanted to start your hike from the Kanc and hit East Osceola first, that could be another option.
Additionally, if you’re worried about how busy the Tripoli Road trailhead might be, this could be a good alternative. You can view Mount Osceola via Greeley Pond Trail on AllTrails. You’ll see the mileage is almost a mile shorter and elevation gain is a few hundred greater. I have not hiked this route so you should take care to research this option.
Recent reviews can provide good information for what to expect. It appears some hikers have had more luck with this trail in the winter as there are plowed out areas along the Kanc to park at and hike to the trailhead.
Mount Osceola Trail
The beginning of Mount Osceola Trail is a gradual incline with scattered rocks over a soft ground. As we were just starting the hike, this felt very easy to climb. That said, it was a little rougher descending due to how much attention you had to pay to your footing on all the angled and slanted rocks.
There were even a few switchbacks at a couple spots and one more set right before the summit (about 2 miles into the hike) which were enjoyable as these are almost unheard of in the Northeast. Overall the trail was very well-groomed with little to no overgrowth at the edges. I wouldn’t be surprised if this was due to how many hikers use this trail all summer so they take extra care to maintain it.
For the entirety of the Mount Osceola Trail before Mount Osceola’s summit, there was nothing too technical and nothing crazy steep. This is definitely one of the more friendly trails of the NH48.
Near the top we first passed an old firetower site that marked the true summit. There were some side paths that we didn’t choose to explore, but if anyone has any insight feel free to leave a comment below this post! Finally, just ahead there was a newer constructed firetower and huge ledge that we walked up to.
Trail Stats
If you’re interested in the specific activity I recorded for this hike it can be found at Mount Osceola and East Osceola on AllTrails. From this link you can also get to the original trail link to view other reviews and conditions in the app.
Mileage: 7.67mi
Elevation Gain: ~2,861ft
Date Hiked: July 30, 2022
Moving Time: 4h 36min
Parking:
Tripoli Rd
or
43.98343, -71.55873
Mount Osceola’s Snack-Worthy Summit
The open summit of Mount Osceola I recorded as just under 3 miles into the hike but in contrast, the sign at the trailhead says it is 3.2mi. The views are amazing! As I mentioned, my group started after 7am and we only encountered 5 people when we first made it to the ledge. After our hike to East Osceola and back though, there were easily 30-40 people in the vicinity of the summit.
We even saw over a dozen dogs that day! If you like the peace and quiet on the trail, I definitely recommend getting an early start on this hike. If you are a bit more social and unconcerned with parking though, then I wish you the best of luck haha.
The views were absolutely inspiring and as I write this post all I can think about is how much I would like to revisit this mountain this summer.
Hiking from Mount Osceola to East Osceola
As you leave Mount Osceola and head over to East Osceola, you start descending pretty quickly. Remember, if you just want a quick day hike with breathtaking views, you could just head back to Tripoli Road after you are done on Mount Osceola.
There will be a lot of open rock so take your time picking your path. The descent doesn’t last too long (you’ll have to ascend again to reach East Osceola) but it is the most technically challenging part of the hike. This tricky portion is referred to as the Chimney.
While the Chimney is the steepest section, we actually found the rocky part between it and Osceola harder, especially when returning.
A Note on the Chimney
My friends and I thought the Chimney was actually extremely fun both descending and then coming back up it. As you approach to climb down it, you may notice a path to the left that avoids going straight down the rock. Going down this path is an easier route and very well worn, but in my opinion not as gratifying!
We all chose to climb down the main portion of the Chimney and were glad we did! It only took a minute of looking down for the best route and then sort of lowering ourselves down onto the next step. It was definitely a very dry day though and I could see how it would be a little sketchy after (or during) some rain.
Coming back, the climb was really entertaining as well but I should say that rock scrambles are some of my favorite parts of any hike! Overall, the Chimney was much shorter than I expected. It only took a couple minutes and maybe three big steps to figure it out.
Stumbling Across the “Summit”
After the Chimney, you still have to do a short stint back up to reach East Osceola’s summit. East Osceola is almost exactly 1 mile past Mount Osceola, so recorded as just under 4 miles from the Tripoli Road trailhead. Note the trail sign from the parking lot says it is 4.2 miles away from the lot.
East Osceola truly came out of nowhere. It is a wooded summit and it feels like you are walking a flat trail until the trees open up a bit and you stumble on the huge cairn that marks the top. We exchanged looks that said, “Is this it?” because we couldn’t believe we’d already made it over to our second peak.
While there are no views at the actual East Osceola summit, there’s still quite a bit of space for hikers to rest while others walk by on the trail. Also, if you walk farther around the bend for another minute, there’s a tiny outlook. It’s not much, but it’s always worth another look at some mountain views!
We did not continue on the trail past that one lookout, which would have eventually hooked up with Greeley Ponds Trail. Instead, we turned around to head back to Mount Osceola and ultimately our car. There were a ton of people (and dogs) hiking as we made this trek back!
We crested Mount Osceola again, and man would that be a great spot for a summit nap haha. The ledge is so big that it’s great for a group to hang out on, rest, chat, and have something to eat. We took our time descending back to the parking lot and though it took a little longer than expected it wasn’t too challenging overall.
I hope you enjoyed reading about hiking Mount Osceola and East Osceola and the images I was able to share. If you found this helpful, please let me know. Now I’m dying to go hike these mountains again after revisiting the images for this post!
As always, the comments below or my Contact Page are open for questions. If you enjoyed this post, you may also enjoy reading about some other short hikes with fabulous views such as Bald Mountain in NY, or Mount Israel, Mt Prospect or Mt Agassiz in NH. Thank you for reading and sharing!
