Trail: Mount Osceola Trail
Miles: 8.4
Hours: 4 hiking; 4:45  total
Level: Moderate

September 8, 2019

Mt. Osceola (4,315’) is one of the easiest 4,000-footers to conquer. If you are just starting on your 48 4,000-footer journey or simply want an easy hike to a higher elevation, I would recommend Mt. Osceola. Although it does not have 360° views, it still is beautiful! AND if you want to tack on another 4,000-footer, you can hike it East Osceola (4,157′)!

NOTE: This is an out-and-back trail gaining over 2,000 feet. If you decide to add on East Osceola, be prepared for one section of the hike to be VERY STEEP. It is called the chimney, and it is not as scary as it sounds, but it is good to know you’ll come across it.

Sam and I began hiking around 7:30 AM on a cool September morning. This was my fourth time hiking Mt. Osceola but Sam’s first. This was also Sam’s first 4,000-footer hike, so I was excited for her to experience the hike! The first part of the hike was very flat and open. It was a classic bait and switch because the trail quickly became cluttered with larger rocks. After the first mile, the trail had switchbacks winding up the mountain with smaller rocks, so our footing was more secure. The switchbacks made for an easier, more gradual climb to the summit without too many steep sections. However, as we approached the summit, there were rock scrambles that added some difficulty and fun! The trail was a little wet, so we had to be careful on this section as the rock slabs were primarily smooth, flat and slippery.

The entire trail was within the tree line, so Sam didn’t get a sneak peek of the view. Because the trail never went above the treeline, most of the summit is covered in trees, but there is an open section that offers beautiful views. Once we cleared the end of the trail, we were greeted with NO VIEWS! We were in the clouds, but they were moving quickly, so we knew we would have some amazing views looking east soon! There are a few concrete slabs on the summit which used to hold a fire tower. It was built in 1910 but removed in 1985. I wish it was still there because it would give some breathtaking views above the treeline.

We reached the summit around 9:00 AM and were surprised by the lack of people. This summit is usually moderately packed, but there were only a few other groups of people when we reached the summit. We took a short break here before heading our way to East Osceola.

The trail to East Osceola was to the left on the summit and immediately began to descend, so we knew we were going to make that up somewhere soon lol. The hike over to East was very rocky and very easy. There was one point where we were on our hands and bums climbing down a ridiculously steep section. Once we reached the bottom, I looked back and realized that was the chimney! We descended via the bypass which I HIGHLY recommend doing. I was excited to ascend the chimney on the way back. 

Looking up at the chimney

Looking up at the chimney


Soon after, we were at the summit of East Osceola at 9:45 AM! It was completely wooded with only a rock cairn noting the summit. There were beautiful views before the summit but nothing that compared to what Mt. Osceola offered. We stayed at the summit for a few minutes before heading back to Mt. Osceola with our fingers crossed the clouds cleared.

Summit of East Osceola

Summit of East Osceola

We ascended the chimney which was NOT as bad as people say, but it was not for the faint of heart. We climbed about 20 feet vertically which was exhilarating and fun! If you did not feel comfortable going up the chimney, you could easily ascend the bypass again. Once we passed this section, it was a gradual incline to Mt. Osceola’s summit. 

We reached the summit at 10:45 AM, and FINALLY, the clouds had cleared! We were rewarded with an incredible view! It was Sam’s first time experiencing a view like this in New Hampshire, so I was super excited for her! We stayed on the summit for a bit enjoying the views and our trail mix. I was SO IMPRESSED with how Sam did hiking. She was an amazing hiking partner and pushed herself to complete the hike. I love that she found a love for these mountains like I did a few years ago hiking the same mountain.

As we began our descent the wind picked up, so we were happy to be below the treeline again. The descent was fairly quick and easy. We picked up our speed as we reached the switchbacks and were ready to be back in the car to eat our lunch! Soon enough, we arrived at the car at 12:15 PM happily eating our peanut butter sandwiches.

As I said above, this is one of the easiest 4,000-footers to conquer with a view. There are other hikes to smaller 4,000-footers that are considered easier, but they do not have a view. If you are looking to conquer your first 4,000-footer and want a beautiful view, I would recommend this hike to you!