I hiked this trail the end of May and am writing about it now so it won't be as precise as my newer hikes so I do apologize! I decided to hike East Osceola and then continue up to Osceola as East was a viewless summit. I figured I'd have a great view to look forward to. It was drizzling out and unfortunately very foggy. I started on the Greeley Ponds Trail. The trail was very wet, but there was a network of log boardwalk set up. There was only one stream crossing.
Stream Crossing Greeley Ponds Trail
After about a mile or so into the hike, you will take the Mt. Osceola Trail which branches off to the right. The Mt. Osceola Trail is where the hiking really begins. About a mile after beginning the trail, it opens up for a nice view of the ponds and surrounding area before returning under treeline. There is a steep, but short section of the trail as you approach the east peak of Osceola which has a wooded summit.
Summit of East Osceola
From this summit, you begin west and descend quite a bit before the climb picks back up. There was a good mix of steep and flat trail heading up toward the peak of Osceola.
Snow on the trail at the end of May!
Eventually you will approach the chimney. It does require a bit of scrambling, but is fun and has some excellent holds! The rest of the trail continues steeply until you reach the large, open main Osceola summit.
Steep section of the trail approaching the Chimney
Summit of Mt. Osceola
You should be able to see the Waterville Valley area and the Tripyramids, but as you can see, I had no views that day. It was still pretty amazing being near the edge in the clouds!