Hike Mount Osceola from Tripoli Road

Hike Mount Osceola from Tripoli Road

3.2 miles to Mt. Osceola Summit, elevation 4,340 feet
+ 1 mile to the East Peak, elevation 4,156 feet
Time: 5-7 hours round trip
Difficulty: Weekend Warriors

Despite being hard to spell, Mt. Osceola features two peaks on the White Mountains Four Thousand Footers list, a moderately challenging trail filled with rock-hopping fun, trance inducing views of the Sandwich Range Wilderness, and a steep chimney climb to get the heart pounding. Add that the trailhead is easily accessible from I-93, and what’s not to love about this hike?

Osceola Trail Sign

Both of Osceola’s peaks are reached via the¬†Mount Osceola Trail, an up-and-over trek from the Tripoli Road to the Greeley Ponds Trail on the Kancamagus Highway (Route 112) side of the mountain. The ascent from Tripoli Road, detailed here, is considered the easier of the two routes. Those looking to avoid the chimney altogether can hike to the main summit through this route without having to cross over to the East Peak.

Osceola Trail Beginning
The flat and easy going is short lived on the Mt. Osceola Trail.

The beginning of the Mt. Osceola Trail from Tripoli Road is flat and smooth, which is a classic bait and switch. The trail quickly becomes littered with rocks and boulders that are impossible to step around. The early going of this hike is like rock-hopping a river crossing, sans water. The footing gets a little more secure after the first mile when the climbing picks up with switchbacks that wind up the mountain.

The switchbacks keep the climbing manageable for hikers of all ages and abilities. There’s nothing too steep or challenging on the Tripoli Road side, it’s more of a consistent climb for 3.2 miles. That said, there are a few places with sheets of exposed granite that could be slippery in wet weather.

Osceola Granite
A few open granite slabs are no harm, no foul in fair conditions, but be careful in wet weather.

The entire hike until the summit is within tree line. There’s a good outlook just prior to the summit, followed by a short and flat stretch to the exposed top.

Osceola Vista
The pre-summit outlook.
Osceola Summit Approach
The final approach to the Mt. Osceola summit.

At 4,156 feet, Mt. Osceola is the highest peak in the Waterville Valley area. The open summit with views of the Sandwich Range Wilderness and the Tripyramids, was once home to a fire tower.

Osceola Summit
The concrete bases to the old fire tower are still prevalent on the Osceola Summit. There’s an open ledge here with views to the east.
Osceola Summit View of East Osceola
The view of East Osceola from the main peak.
Osceola Summit View Sandwich Range
Looking at the Sandwich Range Wilderness and the Tripyramids. Unfortunately this shot was taken into the sun, and thus doesn’t do the view justice.

The descent from the main summit to the col between East Osceola is a mix and match of alternating flat stretches with steep and rocky stints. While most trail talk is centered around the Osceola chimney, and rightfully so, there’s some sweat to be expelled before you get there.

Osceola Descent Col
A steep and rocky section between the main summit and the chimney.

The chimney is the final drop to the floor of the col. It is a vertical descent of about 20 feet with plenty of hand and foot holds. There’s a moderately less intimidating way around to the left that climbs down the rocks at an angle instead of straight up and down. Looking down from the top, it appears worse than it actually is.

Osceola Chimney
The Osceola chimney.

Several parents on the summit were asking if their kids could do it. I always find this question funny, as if one can assess a child’s hiking ability and ambition by simply looking at him or her. While my two year old would probably demand “I DO IT!” this isn’t something I’d recommend for kids. Heck, there’s plenty of adults that would prefer the alternative route, and there’s no shame in it. Ultimately, if you aren’t feeling good about it, or the conditions aren’t favorable, better safe than sorry. Not that safety is fully guaranteed on the alternative route…

Osceola Chimney Alternate Route
The alternative route around the chimney isn’t exactly free and clear from danger. Many people I met on the trail were going down the alternative route and up the chimney, which seemed a wise decision. A couple teenagers even did it multiple times to get the full experience of going up and down each way.

From the col, the Mt. Osceola Trail climbs a hearty 0.4 miles to the East Osceola summit, which isn’t much to blog about. The East Peak is within tree line and distinguished by a large cairn. There aren’t any views at the summit, but there’s a lookout spot shortly thereafter.

East Osceola Summit Cairn
The summit cairn on East Osceola.
East Osceola Lookout
The view from a lookout just after the East Peak.

From the East Peak I continued climbing down a couple steep sections and across the knob to a lookout on the shoulder. It’s worth noting that this hike could be turned into a loop by completing the Mt. Osceola Trail and connecting onto Greeley Ponds Trail. Doing this will require pavement hiking on the Tripoli Road to get back to the trailhead parking lot.

East Osceola View Osceola
The view of Mt. Osceola from the lower shoulder on East Osceola.

Directions to Mt. Osceola Hike

Take I-93 to Tripoli Road, exit 31. The Mt. Osceola Trail parking lot is 6.6 miles on the left. It’s worth noting that the Tripoli Road is closed in the winter. Also, the trailhead parking lot is small and can get filled quickly, so it’s best to arrive early. Here’s what it looks like if you don’t:

Osceola Trail Parking Overflow
Osceola Trail parking overflow stretched as far as the eye could see in both directions on this day.


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