Between the Kancamagus Highway and Waterville Valley, the summits of Mount Osceola and East Osceola can be reached in two different directions on short, steep trails. These two 4,000 footers are connected by a mostly wooded ridge with a short, steep section known as the chimney. While Mount Osceola offers an open summit with gorgeous views, East Osceola is a mostly wooded summit.
In this article we’ll describe the two different hiking trails to get to these summits.
Quick Look at the Mount Osceola and East Osceola Hike
There are two trail options to get to the summits of Mount Osceola and East Osceola. You can ascend from Tripoli Road via the Osceola trail, or via the Greeley Trail off the Kancamagus Highway.
Osceola Summits via Greeley Pond Distance: 6.8 miles Elevation: 3,000 feet Difficulty: Challenging
This trail starts off gradual for the first mile than ascends steeply to the summit of East Osceola. There is one turn to go right off the Greeley Pond Trail that is well marked. Between the two summits, the trail descends and you will ascend the small steep chimney section to get up to summit of Mount Osceola.
Osceola Summits via Osceola Trail Distance: 7.4 miles Elevation: 2,850 feet Difficulty: Challenging
This trail is more gradual for the duration of the hike and is considered the easier of the two hikes. There are some switchbacks before you reach the Mount Osceola summit. You then descend down to the chimney section before reaching the shorter summit of East Osceola.
Both trails offer similar rocky hiking experiences with some rock scrambling and steep section, although the trail from Tripoli is easier. We most recently hiked up the trail via Greeley Pond and found this trail more challenging that we anticipated. Both trails take about 5-6 hours to complete mostly due to the rocky trail conditions.
Things to Know about Hiking Mount Osceola and East Osceola
Best Time of Year to Hike Mount Osceola and Easy Osceola
The best time ofyear for most hikes in the White Mountains is May-October when there is no snow and ice. Spring is often buggy with black flies early in the season and mosquitos throughout the spring and summer. You can also enjoy much of the White Mountains in the Winter. This hike is relatively protected, but there are several steep sections that could be challenging in the ice and snow.
How hard is the Mount Osceola and Easy Osceola Hike?
This is a challengings little hike. Since the total distance of both trails is around 7 miles, there are several steep sections, especially ascending via the Greeley Pond Trail.
How long does it take to climb Mount Osceola Hike?
Both trails take between 5-7 hours to complete. We hiked the Greeley Pond Trail route to Mount Osceola in about 5.5 hours. Due to the bugs we did not stop much. If you plan to eat a longer lunch at the summit, give yourself a bit more time.
Parking for Mount Osceola
To hike Mount Osceola via the Osceana Trail, park at Tripoli Road in Livermore, New Hampshire. This is about 7 miles off route 93. The parking lot has a small fee for parking that can be paid right at the parking lot.
If you are hiking via the Greeley Pond Trail, park in the small lot off the Kancamagus Highway near Lincoln. The parking lot has space for about 5-7 cars.
See more hikes in the White Mountains of NH.
East Osceola and Mount Osceola Trail Map
Details of the Mount Osceola and East Osceola Hike
Via Greeley Pond Trail
This trail starts at a small parking lot and walks through a mostly flat and wet area for the first 1.3 miles. There are mutiple small and medium sized streams and log bridges to cross on this section of wooded trail. We did not have difficulty crossing the stream in early June, but there is one crossing that could be challenging in early spring.
At the first trail junction, turn right towards the well marked trail up Osceola. The summit of East Osceola is just 1.5 miles from this sign but is up a significant climb. This section of the trail is steep and rocky with some scrambling in a few places and will really get your heart pumping.
The summit of Mount Osceola is wooded but you will get a few views through the trees once you reach the ridge just before the summit. There is a rock pile at the summit.
Just after the summit, the trail descends again to the saddle down a steep rocky section with a few viewpoints along the way. At the base between the two peaks, you will come to the chimney section. This is a short (20 feet) section that is steep with sometrue scrambling to get up. While this was fun and steep, it’s only a bit more challenging than the other steep sections along this hike.
After the chimney, the trail is slightly more gradual to the summit of Mount Osceola. This summit offers excellent 180 degree views. Overall this is the more challenging way to summit Mount Osceola and East Osceola.
Via Osceola Trail
This easier route starts off mostly flat before becoming more rocky and challenging. After about 1 mile, the trail begins a series of switchbacks up the mountain. The entire route is generally gradual with a few sections of granite that can be slippery when wet.
The first lookout is just before the summit, otherwise the trail is wooded. Once you reach the summit, you will descend down to the chimney and back up the steep hike to East Osceola.
While the chimney section is steep, it is short and with the exception of very young kids it doable for most people. Our dog was able to make it up and down although it was a bit nervewracking (for us, not her).
See more about current trail conditions by reading the reviews on All Trails.