NH48: Mount Osceola and East Osceola
Hiked: Saturday, June 12, 2021
NH 2 & 3/48
Peakbagging is something I first discovered in Washington state, having lived amongst other mountaineers and mountain enthusiasts. When Analisa (who writes the most amazing gear and mountain adventure reviews HERE… especially for gnarly women!!) introduced me to Washington’s Bulger List on our climb of Silver Star Mountain (still one of my fav mountain days evah), I thought it’d be pretty awesome to move towards the 100 high peaks in Washington. Yet, a part of me didn’t feel like it’d be achievable. A part of me knew I’d eventually leave the PNW. (Regardless, I will one day return… there’s SO MUCH more to climb!)
With my decision to begin baggin’ peaks in the northeast, the NH48 was a no-brainer. For my second peak, I was itching for more of a view than my virgin hike on Tecumseh (and perhaps less of a staircase?). In true peakbagger spirit, I wanted an easy way to knock two peaks off the list and still be home to work on my Etsy site! Discovering I could do Mouth Osceola and East Osceola in one trip AND drive 2.5 hours (one of the closer mountains to Boston!) was a WIN. With summits separated by one mile, there are a few ways to bag both Osceolas. I opted for the longer hike, starting from Tripoli Road and hitting Mount Osceola before East Osceola.
Two more peaks bagged with numbers 2 and 3/48… donezo! Read on, mountain enthusiasts… that is if you’ve navigated back from researching peakbagging… peakbagging.com is a great place to start by the way… and there’s lists for pretty much every area across the U.S., including San Francisco area!
Distance: 8.4 miles (round trip)
Elevation Gain: ~2,900 feet total
Highest Elevation: Mount Osceola Summit (4,340 feet), East Osceola (4,156 feet)
Route: Out and back; Mount Osceola Trail trail up & down. There are two other route options to bag both peaks (see end of the post).
Drive from Boston: 2 hours, 25 minutes
Parking/TH: Tripoli Road, $5 at trailhead to park if you don’t have a pass. (NOTE: this road closes in the winter!)
Weather/Conditions: Mildly sunny and 65-70 degrees. Literal perfect hiking weather. Lots of rocks. Could’ve worn hiking boots instead of trail runners! Glad I didn’t bring trekking poles bc they would’ve annoyed me for sure.
Highlights: SOLO hike! The chimney between Mount Osceola and East Osceola (love me some scrambles!!), tons of rock/exposed granite, a few switchbacks (basically a unicorn on east coast trails!), quality conversations with strangers/new friends on the trail!
As my first true solo hike in the White Mountains National Forest, this was a special day. While I always appreciate company, I absolutely love heading into the woods alone. Of course, being mindful of the ten essentials and navigation is key to doing this confidently. Given I’m new to the Whites, I have spent lots of extra time researching routes and paths around these mountains. As I learn more, I discover tons of resources for hiking in the White Mountains to achieve my goal of hiking all 48 peaks! One of my favorite resources has been a Facebook group called “Hike the 4000 footers of NH!” People post their recent experiences (so fun to read), photos, trip reports, recommendations, etc. It’s this group that taught me to wary of black flies (still haven’t met any yet, thank goodness!) and the “mud season” in NH, plus keeps my stoke alive for hiking, exploring, and (of course) peak bagging!
I started the day mildly early, leaving my home in Brookline, MA at 6AM, jamming to my reggae “vibin” playlist (honestly, what’s better musical company on a sunny day??). Not quite an alpine start, but I wasn’t trying to be a hero this weekend! The drive to the trailhead is pretty straightforward – ride 93 until the Tripoli Road turnoff! I decided to go a little further on 93 to stop at my new breakfast stop in Lincoln, NH! The White Mountain Bagel Co has bangin’ cream cheese, egg sammys, and bagel options (even for a New Yorker). PLUS, you can order ahead & pickup at the window! I had my order in by 7:30, picking it up at 8am! Everything bagel with veggie cream cheese, don’t mind if I do!
I arrived to a full parking lot at the Tripoli Road Trailhead, but there were only a few cars parked on the road. FYI, you can only park on the SOUTH side of Tripoli Road (that’s on the right as you approach the trailhead). BONUS, there’s a toilet at the trailhead, which is great for long drives in. I need to purchase a new America The Beautiful pass, so I paid the $5 at the TH and put the stub in my car, paying my admission to a beautiful day with Mother Nach.
**Don’t forget to pay!!** Forgot cash money? There’s a gas station/7-eleven in Lincoln (across from bagels!) that gives $5 or $10 cash back for debit purchases.
The trail begins with a game of hop & scotch around the rocks and pretty much continues for the first mile. When the path evens out, I suddenly found myself meandering on switchbacks! Wait, what?! For a moment, I had to remember where I was! The trail had serious Mailbox Peak vibes from Washington state, but with a few more rocks in the path. I had flashbacks to the uncountable number of switchbacks I’ve walked in all my hiking on the west coast. On this trail, I counted maybe five. Maybe. Someone recently told me I have a perfect combination of OCD and ADD – I start counting something, then forget I am counting something because I get distracted. Like when I make coffee in the morning, I always count 30 seconds to let my fresh grinds bloom as I pour the first 100-or-so grams of water on my pour over. After 30 seconds, I am supposed to top it off to 355 grams. However, I sometimes (always) forget that I was counting to 30 and, by the time I remember, my little kitchen scale has auto turned off. Dang it, battery saver! How much water did I put in already? Who knows. Oops. I’d like to think not having full OCD and ADD makes me more functional… right? And I promise the coffee always tastes good.
So yeah, don’t quote me on the number of switchbacks (:

From the Tripoli Road trailhead, it’s 3.2 miles to Mount Osceola’s summit. I was movin’ and groovin.’ Usually, I estimate about 1 hour per 1000 feet of elevation gain, but I hit 1500 in an hour. I was feelin’ GOOD. Love getting into a rhythm. There weren’t any bugs. The sun was shining. Perfect temps for me to wear my sun hoodie and leggings without beads of sweat on my face. Ahhhh, mountain serenity.

As the trail transitioned to slanted granite, the trees also began to open up. To the east, the mountain peaks really piqued my curiosity for what I’d find atop Osceola! I kept looking back, like checking the rearview mirror to make sure I didn’t miss a single view. #lookbackatit (sorry)
Mount Osceola’s summit had a magical way of sneaking up on me. I sensed I was getting closer, but as I came out of the trees and walked onto the granite summit, I wasn’t entirely prepared for the expansive views! You could see the path to East Osceola and the Sandwich Range, including Mount Tecumseh (my first NH48!). While it’s not a 360-degree view, it was pretty spectacular. Layers on layers of mountains. Yum.

There were tons of places to sit and enjoy the view, so I grabbed a snack before heading onto my second peak: EAST Osceola! The one-mile path to east started immediately downhill. There was one section that smelt like the infamous “chimney” portion of the hike. It was a sit and scoot on my booty kind of portion of the trail, but lo and behold, it was not the chimney. Eventually, the path started heading uphill… which I thought was a relief until I realized I was huffin’ and puffin’! Felt good to get the heart pounding. Views kept peeking out between trees. This path was less rocky than the path to Mount Osceola, but had a bigger sections of rocky obstacles.
FINALLY, I got to the chimney! Hiking from Mount Osceola to East Osceola, you end up going DOWN the chimney. I didn’t even know it, but I ended up hiking down the bypass (dang it!). On my return trip, I’d end up choosing the true chimney! After a mile of walking from Mount Osceola, I arrived at a giant cairn, which signified I was on the top of a mountain, but didn’t really feel like it. Turns out, East Osceola is completely engulfed in trees. Worth it still? Duh. Bag those peaks!

I snapped a quick foot selfie with the summit and turned right around to enjoy more snacks at Mount Osceola. I walked amongst other peak baggers and mountain enthusiasts. Everyone was so encouraging. “You’re almost at the chimney!” I heard people sharing their number. People were even cheering on each others’ dogs. A gal I met from Texas/Montana/living the vagabond life (awesome) was struggling to keep her doggo moving on the chimney, but the sweet pooch made it!
The chimney climb from East Osceola back to Mount Osceola was more what I was lookin’ for! When you arrive at the chimney, you can go right or left. RIGHT=bypass, LEFT=chimney.
Choosing the chimney, I had flashbacks to climbing Mount Shuksan’s Fisher Chimney route. I knew I could do this. And I could have FUN while doing it! Hands and feet engaged, breath rhythmical, mind in the flow. Place a hand, place a foot, stand up. Look above, find your next move. Breathe, you got this.
I feel this must be stated: If you opt for the bypass, I don’t think ANY less of you! We all have limitations to what we are willing & able to do. Despite my experience with scrambles and rock climbing, I could understand how the vertical, unsupported climb can feel very exposed. Recognizing all is temporary and breathing is one way to move through the discomfort if you really want to give the chimney a go!


En route back to Mount Osceola, I found a hiking companion who said they were trying to keep up with my pace. (I was also trying to keep up with my pace, haha). This was the first person I spoke to for more than 1 minute spontaneously on a trail… in a very, very long time. I have to admit, my instincts were wondering what this person wanted. Turns out, conversation was the goal. How refreshing. Not something I was really used to in the Pacific Northwest! Of course, intentional meetups with new people always led to incredible conversation… but it wasn’t often I came across someone on the trail who wanted to know some of my story.
This wasn’t the end of quality trail conversations! I chatted with the vagabond and her precautious/easily distracted pup, then spent 2 miles hiking with a woman who I gave Tylenol for a headache (this Wilderness First Responder is always prepared!). We didn’t even know each others’ name, until her husband came strolling behind us. She was lovely company and our conversations flowed effortlessly, despite whatever differences we had. These magical conversations and people were just another reason to appreciate exploring more mountains on the east coast.
At the end of the hike, I was feeling fulfilled… with sore ankles and all (did I mention having a bit of ankle support would have been a good choice for this rocky hike?). The views were far more expansive than Tecumseh and I affirmed the summit crowd at my first of the 48 was actually incredibly bizarre haha. Today’s vibe was far more grounding and connecting. While East Osceola had no views at the summit, the path between the Osceolas is 100% worth it… if not to simply give the chimney a try.
What peaks are you baggin?!
Cheers to 2+3/48! Read all my posts about the NH48 here!

Other options for this hike (reference is 4000footers.com):
- Greeley Pond Parking: Begin on the Greeley Pond trail via Kancamagus Highway (Hwy 112) and travel 1.3 miles to a fork in the trail, then follow Mount Osceola Trail for 1.5 miles to the summit of East Osceola. You can continue 1 mile to the summit of Osceola from there. Retrace your steps back. Total mileage is ~5.6 miles.
- Traverse: Summit both Osceolas via a 7-mile hike from Greeley Pond Trail to Tripoli road or vice versa. You would need a car spot at one of the parkings areas.