East Osceola and Osceola via Greeley Ponds and Osceola Trail

After our first hike up Tecumseh, we decided to hang out in the Waterville Valley area for an overnight camp and another hike in the morning. We ended up staying at a campground on the Kancamagus Highway for $20, but we decided later that it would have been a bit nicer to purchase a permit and stay along the riverside on Tripoli Road. Either way, we got a decent night’s sleep (the tent worked perfectly and set up was a breeze!) and had an awesome breakfast at Flapjack’s in the town of Lincoln the next morning. At 11:00 AM we pulled into the parking lot for the Kancamagus side of the Greeley Ponds trailhead. Our intent was to hike both of the Osceolas for a total of 3 peaks in the one weekend.

The Greeley Ponds Trail was very scenic with an easy grade and logs covering most of the muddy patches. There were two river crossings right at the beginning, one of which was easy to cross, and the other a bit wider and more difficult. We became a little confused when the trail would branch off in other directions, but after consulting our guidebook, we realized that there were also ski trails in the area marked by blue diamonds, so we avoided those. After a 1.3 mile walk we reached the trail’s intersection with the Mt. Osceola Trail, which veered off to the right.

The Mt. Osceola Trail was a bit more difficult because of the steep grade and poor footing in some areas, especially considering how sore our legs were from the day before. We took lots of breaks, but were treated to tons of awesome views through the trees (especially at a steep sloping rock face about a quarter of the way up the trail). The entirety of the trail was easy to navigate with no confusing paths branching off from the main one until just before reaching the first peak at East Osceola. This branch, which runs off to the right on flat ground at the top of a steep rocky climb, leads to an amazing view of both East Osceola and Osceola, giving us a great perspective on what was to come for the rest of the day.

After taking another long break, we headed off towards the east peak. East Osceola is horribly disappointing, the only view being a little ways before the peak. The top is marked by a pile of rocks (nature’s glory at its finest) and was really buggy, so we didn’t stay long. The pass between the two peaks was beautiful, offering tons of great views and a really fun vertical climb up “The Chimney.” At 3.8 miles, we finally reached the peak around 3:00 PM. Osceola offered the most amazing view we have seen on any of our hikes thus far, so while fighting off flies and snacking on sandwiches, we basked in the awesomeness on the clear patch of rock that marked the peak before heading back down the way we came. To no one’s surprise, Captain Feathersword encountered some paparazzi at the top (a really nice group of hikers asked to take his picture). If anyone has wondered why Captain Feathersword’s head is so large, it’s because it’s filled with delusions of self-importance and global celebrity status.

The trip down was relatively easy, with far less stops for breaks, but we also slowed down the pace to avoid breaking our ankles. We probably did more butt-sliding than walking. We reached our car at 7:00 PM for a grand total of 8 hours hiking that day (Captain Feathersword was pretty sore). We reached our goal of hiking three 4,000 footers for the weekend, which now brings our checklist down to 45!


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