Hiking Osceola Trail from Tripoli Road: Trip Report

One particularly sunny and beautiful mid-July weekend, Erich and I decided to take a hike. Erich is quite new to hiking, having never really done a full day, oh-my-god-my-knees-hurt hike before we met. In an effort to get him to see the joys of hiking, not just the pains, I sought out a moderate level hike with stunning views. The choice was obvious: the Mt. Osceola trail from Tripoli Road.

This hike hit all the major points: Mount Osceola is one of the 4000 footers of New Hampshire’s White Mountains; we could easily bag a second 4k-er, East Osceola, without adding too many miles to our day; it was a fairly moderate hike, only 3.5 miles from Tripoli Road to the summit; and the denizens of the New Hampshire Hiking Facebook group I joined said that it had some of the best views in the Whites.

Decision made. We were hiking Osceola and East Osceola.

erich points towards the pemigewasset

Everything You Need to Know about Mount Osceola

Mount Osceola is a peak in the southern White Mountains. Along with its sister peak, East Osceola, they make up two of New Hampshire’s 48 4000 footers in. Osceola sits at a height of 4,315ft (1,315m) and nearby East Osceola reaches a stately 4,156ft (1,266m).

So they aren’t the tallest mountains ever.

But don’t let that fool you. As anyone who has ever hiked in New Hampshire can tell you, the modest height of these mountains hides some surprisingly tough terrain. The trail from Tripoli Road to Osceola is fairly easy, with only a few rough granite patches, but the trail along the ridge from Osceola to East Osceola features some steep granite stairs and a spicy little section known as “The Chimney”.

But I’m getting ahead of myself.

The mountains are named after the famous Native American warrior, Osceola, born a member of the Creek tribe, he and his mother became refugees and they ultimately were taken in and became members of the Seminole Tribe. Osceola grew to become a fierce warrior and powerful leader, taking on the American Army when no one else would. He was captured in a deception that is, to this day, one of the great shame of the U.S. Military history, and many monuments around the nation are named in his honor, including these two peaks in New Hampshire.

DSC00833

Hiking Mount Osceola Trail from Tripoli Road

The trail from Tripoli Road is unexpectedly smooth and gentle. Trails like this are something of a rarity in New England, where most of the paths were cut by anxious old Yankees who seemed more interested in punishing their knees than having a nice day walking in the woods.

At any rate, the trail is pretty easy. It starts out gentle and stays pretty gentle all the way to the top. There are some really nice spots along the way where the trail levels off completely and you meander through piney forests and weave in and out of hardwoods.

As you near the top, the trail steepens a little and there is a slight scramble, not even a scramble really, just a small climb up a wide flat granite section. It is closely lined by trees, so the smooth rock, though slippery when wet and probably a disaster in the winter, is nothing to be afraid of.

Erich and I reached the top before we’d even started to feel the hike in our legs.

Mount Osceola view from the summit

Summit Views

The best part of hiking Osceola is the reveal. The entire ascent is forged through a tunnel of trees, not a view to be found. As you near the summit the trail levels off and, on most days, you hear the sounds of people chatting and hanging out. Pass through the last barrier of pine trees and you emerge onto the flat granite summit of Osceola.

The world opens up before you. Pine clad mountains stretch for miles, Tripyramid stands tall and proud across the Waterville Valley. To the north, the Pemigewasset beckons with it’s multitude of rocky peaks and dense, eternal forests. It really is one of the more remarkable views in the White Mountains.

ridge and chimney to east osceola

The Trail to East Osceola and the famous Chimney Cliff

From the summit of Osceola, East Osceola is a short and steep ridgeline traverse away. Easily visible from your perch on the wide granite peak, bagging them both on the same hike is an opportunity too tempting to pass up.

Leaving Osceola, the trail descends immediately down a long granite staircase, following the bumps and curves of the ridgeline. The trail alternates between steep downhill and short, level sections wherein you truly feel you’re walking the ridge above two sheer mountain walls.

Then you reach most thrilling part of the traverse: the Chimney. This famous cliff begs for you to slip and fall, if not to your death then at least to a broken wrist or two. I exaggerate. In the summertime, it’s a fairly easy, if a bit steep, section of scrambling. There is a slightly easier alternate route off to the left for those who are averse to climbing straight down.

In the winter, this should probably only be attempted with the proper gear and knowledge.

And also I saw some people in their 60s or 70s climb down it. And a dog. And some kids. So, like, chill.

After you descend the Chimney, you quickly reach the saddle and head back up. There’s a nice viewpoint overlooking the Pemigewasset just below the summit, then a little further up another granite staircase and you find yourself at the riveting, jaw-droppingly stunning summit of East Osceola.

Just kidding, it’s tree’d in.

Apparently there are more viewpoints past the summit on the way to Greeley Pond, but they are several hundred feet down a steep trail so, dealers choice. We did not include that in our day hike.

My First Osceola, But Not My Last

I adored this hike up to Osceola. The views from the top of this mountain were classic White Mountains at their finest. In Erich’s words when we got there.

“Oh yeah, I could get into this.”

I’ve heard good things about the approach to the Osceola’s from the Kancamagus. It’s steeper and more grueling but apparently has some stunning viewpoints. A definite must on my list of hikes.

clif views

How to Get to Osceola Trail on Tripoli Road

From Interstate 93 take exit 31 for Tripoli Road and take a right. Follow Tripoli Road for 6.5 miles. You’ll pass through a gate and continue past two other trailheads before you get to the Osceola Trailhead. It will be on your left. Unless you get there early, prepare to park on the side of the road. Parking is only allowed on the right side.


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Hike Mount Osceola from Tripoli Road with this complete guide to one of the most scenic hikes in New Hampshire's White Mountains

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