After consulting John, the other resident, he advised me to take the Greeley Ponds Trail up to East Osceola and then Osceola. I easily found it on Alltrails.com, so I knew were to park.
Alltrails advertises this as a 6.1 heavily trafficked out and back. https://www.alltrails.com/trail/us/new-hampshire/mount-osceola-trail-to-greeley-ponds-trail
I got a later start to the day due to working in the morning and headed for the trailhead. This hike had 2,378 feet elevation gain.
I pulled up grabbing the last spot in the parking lot. You start out the climb at relatively high elevation and gradually meander through the woods across boards and a few stream crossings but it’s pretty manageable until you reach the Greely Pond and Osceola Trail junction. The trail starts to become more rocky with larger scale boulders and the elevation begins to climb.
You have to scramble up a rock slide that provides you with a nice view of the two peaks.
You re-enter the woods walking along the tree covered ridge until you reach the wooded summit. After leaving the summit, you begin to descend with some more views dropping you further down requiring a few scrambling to make it down to only go back up again.
The next highlight is the “Chimney” that is about a 20 foot scramble. There is a slightly less steep bypass to the right that I took on my way back.
I took a much deserved break at the top to soak in the views. The black flies were mildly annoying.
Although it didn’t seem to take much time to get up there. The way down actually took significantly longer. Descending from East Osceola was very technical and slow going until I reached the junction again.
People will often complete the Osceolas and then Tecumseh, which is across the street and down the road a bit for the parking.