Mount Osceola - 4,340'
Hike Statistics
Total Distance: 8.4 miles (with East Osceola Mountain)
Elevation Gain: 2,760 feet
Hiking Time: 6 hours, 20 minutes
Difficulty: Moderate
Season: Fall
Hiking this peak in winter? Click here!
Hike date: 11/07/2020
Description: Mount Osceola is the highest peak in the Waterville Valley Region and offers great views of the Sandwich Range Wilderness, with the Tripyramids and Mount Whiteface front and center. Using the route below, you’ll have the opportunity to summit two peaks, climb a steep chimney, and enjoy nice views.
Want to see some footage of the trail so you know what to expect? Be sure to check out our YouTube video of our hike to the Osceola’s which you can find here!
Trails Used: Ascend via Mount Osceola Trail to the summit of Mount Osceola. Continue along the Mount Osceola Trail to the summit of East Osceola Mountain. Descend by turning around and returning the same way you came up.
Trail Summary: There are two ways to summit the Osceola’s: from Tripoli Road or from the Kancamagus Highway. The easier route is an in-and-out hike from Tripoli Road, which is what we describe here. The trailhead is on Tripoli Road and is marked by a sign. Note that Tripoli Road is usually gated from November to May, so if you are planning to hike the Osceola’s during that time frame, you will most likely have to come from the other side off the Kancamagus. Luckily for us, there was no snow at this point in early November (in fact, it was over 60 on this day!), so Tripoli Road was still open. The trail leaves Tripoli Road and climbs moderately over rocky terrain for the majority of the hike. As you hike along, you’ll begin to climb several series of switchbacks (with good footing and terrain) as you wind your way up towards the top. You’ll know you are approaching the summit when you cross over several areas of slab. Eventually, the trail will reach a large, open rock ledge with fantastic views. This is the summit area of Mount Osceola! From the summit, you can see East Osceola (where you’ll be heading next), the Tripyramids, Mount Whiteface, and several other peaks of the Sandwich Range Wilderness.
The beginning of the trail is moderate in both incline and rockiness
Once you are about halfway up, slab dominates the trail
Be careful! This is a very wet and slabby trail!
Looking east from the summit ledges on Mount Osceola
Looking southeast towards the Tripyramids from the summit ledges
Taking a selfie just below the summit of Mount Osceola on our way to East Osceola
After enjoying the nice views from the ledges of Mount Osceola, it’s time to continue on to East Osceola! As you descend into the col from Mount Osceola, you will face a mix of easy stretches and steep rocky stretches. You will come to a spot known as “The Chimney” on the trail, which is a very steep and rocky area. This chimney is actually easier to go up rather than down. If you are feeling nervous, or prefer not to descend down the chimney, there is a bypass on the left that is slightly less technical and a bit easier. We chose to descend using the bypass, but on the way back we went up the chimney. After the Chimney, the trail climbs moderately (though there are a few steep sections) towards the wooded summit of East Osceola, which is marked by a cairn. There is a nice outlook on your left as you near the summit; the only views from near East Osceola. From this outlook, you can see north into the Pemigewasset Wilderness towards the Bonds, the prominent Mount Lafayette and the rest of Franconia Ridge, Owl’s Head, and many other 4,000 footers and other peaks. After a break at the summit of East Osceola, it is time to head back! To return, you’ll go back the same way you came, which means you will be dealing with The Chimney again and have to go back up and over Mount Osceola again. The descent from Mount Osceola goes fairly quick due to the moderate grades and good footing.
Looking at East Osceola as we head into the col
Adam making his way down the Chimney bypass
Outlook with limited views before the summit of East Osceola Mountain
The wooded summit of East Osceola Mountain, marked by a cairn
Climbing up through the Chimney
Adam almost to the top of the Chimney!
Alternative routes:
We have not yet done any alternative routes to the summit of Mount Osceola. This page will be updated once we have!
Hiking Mount Osceola in the winter
We have not yet climbed Mount Osceola in the winter, but once we do, we will update this page with our full report!
Questions? Comments? Want to share your take on this hike? Get in touch with us using the contact page!
As experienced hikers, we always make sure that we are hiking with The Ten Essentials which include navigation, a headlamp, sun protection, first aid, a knife, shelter, extra food, water and clothes. Overtime, we have discovered some items that we always bring on our hikes and consider them to be our personal, expanded ten essentials.