How to Hike Osceola and East Osceola High Peaks Apart of the 48 High Peaks

August 3, 2025

Two great hikes apart of the New Hampshire 48 High Peaks are Osceola and East Osecola. They are located just outside of Lincoln, NH and are great “beginner” hikes, if you are interested in hiking the 48 high peaks in New Hampshire. However, they are NOT good beginner hikes for beginner hikers. 

If you are unfamiliar with the New Hampshire 48 Challenge, it includes hiking all the mountains in New Hampshire that stand over 4,000ft in height. They have huge elevation gains, nasty climbs (some of them), and beautiful views (most of them). Now, going back to the Osceolas, there are a couple ways to hike them. I hiked it via Tripoli Road which makes the hike a total of 8.6 miles with an elevation gain of just under 3,000ft. You will hike Osceola first then continue onto East Osceola. These two peaks are a great way to get your feet wet with the New Hampshire 48 Challenge. 

In this article, you will read about Mount Osceola, East Peak Mount Osceola, Mount Osceola trailhead, Mount Osceola hike time, Mount Osceola hiking, Mount Osceola chimney, Mount Osceola sunrise, Mt. Osceola and East Osceola hike, Mount Osceola from Tripoli Road, Mount Osceola camping, and more.

This article is all about Mount Osceola.

Mount Osceola:

Mount Osceola From Tripoli Road

Okay, to start, you will need directions to get to the trailhead. From Lincoln, New Hampshire, it is super simple, you will get onto Interstate 93 North then take the exit for Tripoli Road (on 93 North for about 3 miles). Once off the interstate, you will take a left and continue straight for 6.8 miles. A lot of this road is on a gravel/unpaved road. Even though, most of this road is unpaved, it’s very well kept, so most cars should be able to drive on it. In total, this trailhead is about 24 minutes away from Lincoln. Now, if you’re coming from somewhere else, you can click here to find directions (just click, get directions). It’s also pretty easy to get the Mount Osceola trailhead from Boston, MA  or Burlington, VT.

Okay, another way to hike Mount Osceola and East is from the Greeley Pond trailhead (much less popular route). On this approach, you will hit East Osceola then Osceola. You can find directions and trail maps for Greeley Pond here.

{Related Article : Mount Tecumseh}

From Tripolia Road Continued

Once you get to the Tripolia Mountain trailhead and park. First, you will want to go to the self-pay station to get a parking pass for the day. There are also bathrooms here. Once you park, you will go left towards the trailhead.

This trail is very easy to follow, just follow what looks like a trail and watch out for some switchbacks and you will be fine. You can follow AllTrails which is what I did. It’s about 3.2-3.5 miles to the summit of Osceola and it’s beautiful. I would take some time to take in the amazing views at Mount Osceola.

Once you summit Osceola, you will go left to the herd path and follow that all the way to East Osceola. You will encounter the “Chimney.” This is the steepest part of the hike. Stay to the left of it and you will be fine. Or if you want to hike the “Chimney,” stay to your right towards the rocks. You will encounter this section of the trail about half way to East Osceola. East Osceola is about a mile from Osceola. The big rock cairn or pile of rocks is your indicator that you are at the summit. It is a wooded summit with no views.

Getting Back to Your Car

To get back down, just reverse and retrace your step. In total this was about 8.6 miles with just under a 3,000ft elevation gain. I really loved this hike. I agree it is a great beginner hike into the New Hampshire 48 Challenge. The view on Osceola is stunning. In total, this hike took me about about 5 1/2 to 6 hours to complete with breaks. I started around 8:30am and ended a little after 2pm.

Overall, I really liked Mount Osceola and East Osceola. I thought they were great beginner hikes to climb for some of your first New Hampshire 48 High Peaks. What is really nice about these peaks, is that the elevation gain is moderate. I always say, it’s not the mileage that will kill you, it’s the elevation gain, aka it’s all the up you have to climb. While this hike is still difficult and should NOT be attempted by beginner hikers, it is EASIER than OTHER 48 peaks.

More Beginner Hikes/Singular Hikes

Here are some more great “beginner” hikes to start the New Hampshire 48 Challenge. I also wanted to pair all the “singular” hikes or solo hikes apart of this challenge. Most of the hikes you can pair with other peaks, but there are some that are solo hikes.

  1. Mount Tecumseh
  2. Mount Waumbek
  3. Mount Moosilauke
  4. Mount Jackson (or can pair with Pierce and Eisenhower)
  5. Mount Hale (HUGE elevation gain, DON’T let the short mileage fool you, be PREPARED)
  6. Owl’s Head (NOT beginner hike, solo hike, not usually paired with anything)
  7. Mount Isolation (NOT beginner hike, solo hike)
  8. Mount Moriah (NOT beginner hike, solo hike)
  9. Galehead (NOT beginner hike, solo hike, sometimes paired with Mount Garfield)
  10. Mount Carrigain (NOT beginner hike, solo hike)

Overall thoughts about Mount Osceola, East Osceola, and Cabot, I really liked Osceola. I didn’t really care for East Osceola and Mount Cabot. These two didn’t have a view which was a main part of it. Overall, these hikes were not too difficult. They are still work but manageable work. They are good hikes to start your 48 journey on. I hope this article was helpful and thank you so much for reading.

error: Content is protected !!