Nov 13

Hiking the Osceolas

In mid-August the Stonyfield hiking club finally had another get together planned to hike the Osceolas. We were going to go up East Osceola and then head up the chimney and over to Osceola for a double peak. We were supposed to meet at the parking lot of the Greeley Pond trail head at 8am to get started. I live a little over 2 hours from most of the trailheads and was leaving my house about 10 minutes later than I wanted to. I texted one of my hiking buddies to let them know that I was running a little behind. He called me back to let me know that he actually wasn’t making it that day and gave me someone else’s cell to try. I texted them that I was running late and then got back on my way. The thing about most of the trail heads in the white mountains is that they’re not known for their cell service. My friends had gotten to the trail head, waited around a little bit, and then assumed I was coming and started up without me. Thus begins the adventure of my first solo hike!

I pulled in to the parking lot about 15 minutes after our appointed meeting time and debated whether or not I felt safe enough going up on my own. I reasoned that I had all of the supplies I needed, there were dozens of cars in the lot and so there were likely many other hikers on the trail, and I was at most 15 minutes behind my friends and could possibly catch up. So, I started out. I overtook several groups of hikers on my way up the Greeley Pond Trail, but none of them were my friends. At least I felt that I was fairly safe, knowing there were a few groups of hikers behind me, and several more than I could hear a ways up ahead. I kept going, on what was probably the most strenuous trail I had climbed so far. I remember getting to one area of sheer rock face and being mildly terrified at the thought of sliding off the edge and tumbling down the mountain. Thankfully, I made it safely up and across the ledge, and am still here. But it was definitely not an easy climb!

At one point after I felt like I had been climbing forever, I started to actually go downhill pretty steadily and steeply. Luckily another group of hikers was coming up the other way. I greeted them and asked if they knew if I was still on the right path to get to East Osceola’s summit. They informed me that I had actually already passed it and was heading down the other side to Osceola. I felt like kind of a dumbass for a moment, until the woman I was talking to told me that it happened all the time because of East Osceola’s wooded and unimpressive summit. So at least it wasn’t just me! I thought about heading back up, but since I was going to be doubling back to my car the same way I figured I would just stop on my way back. Still no sign of my friends at this point! (And also no trail pictures thus far — I was too disoriented from unexpectedly hiking alone and forgot to take pictures along the way.)

I kept on keeping on and eventually came to the Osceola chimney, which is a steep and jagged climb that leads you up to the Osceola summit. This was actually my favorite part of the hike. I LOVE when I have to climb on a hike. This part was a lot of fun. A little ways after that, I finally made it to the summit of Osceola.

Panorama of Osceola Summit

I heard two girls just under the rock ledge that was directly in front of me in that picture and I approached them to see if one of them would mind taking my picture at the top.

At the Osceola Summit

I thought that the girl taking my picture looked a lot like a friend of a friend of mine and, sure enough, as she was handing me back my phone she said she recognized me too. We took a summit selfie together to send to our friend, who is my work wife and her best friend. We’ve since all been hiking together a couple of times, and those trips have been some of my favorites.


She had reached Osceola with another friend of hers via the Osceola Trail from Tripoli Road. Apparently this is the way most newbie hikers or those looking for a nice, steady climb would take. When I told her I had come up East Osceola she looked horrified. Apparently the hiking team from Stonyfield had picked the hard way up! We parted ways and I headed back toward the Greeley Pond Trail. I paid extra close attention on my way back this time and made sure to stop at the summit, which is where I eventually found my friends. It turns out they had waited for me a little while but never got my text and so went on without me, just as I had thought. What I hadn’t considered was that they might head over to Greeley Pond before actually starting up the mountain. I walked right past them while they were hanging out at the pond and was well on my way up the mountain before they had even started. They were just getting to the East Osceola peak as I was heading back down. They agreed, the view was not much to look at.

East Osceola Wooded Summit

We parted ways as they headed toward the chimney and Osceola, and I headed back toward my car. I got a little nervous on that same rock face on the way down, but ultimately made it out unscathed. And, as an added bonus, the Osceolas are up Rt 16, which means I got to stop at Hobbs Tavern on the way home! Behold, the knuckle sandwich:

Hobbs Knuckle Sandwich

Nothing but claws in that thing. I kind of want to go get one again right now…


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