The Bushwhack of West and Middle Osceola

What I initially hoped would be just another trail run through the White Mountains quickly turned into a search for hidden Perfect single track trail headed to Mount Hancockplaces that most folks have long since forgotten about;

The secret 4000-foot peaks of New Hampshire!

I began with my typical early morning start on the road out of Plainfield and had my GPS set to the Hancock Notch Trailhead up on the famed Kancamangus Highway – a quick (compared to most White Mountain drives for us!) 73 miles away.

The sun was just beginning to make an appearance as I pulled around the switchback and into the lot, where a couple stood taking mountainous selfies and mapped out their day. I took this early start as an opportunity to stretch, ready my running vest and check over everything twice. My Black Diamond headlamp shone the way over the dry, rocky single track into the forest. It wasn’t long before I hit the first junction, swung a left followed by a right onto Hancock Loop Trail.

I was clearly the first on the trails this early morning as I could still smell the bacon sizzling over a campfire belonging to a couple I would later pass as I trekked my way back out. My buzzing legs made quick work of the 1000-foot ascent as I stopped for some summit shots with the Go Pro. I didn’t stay for long on the open summit boulders due to the morning fog laying heavy all around. The next goal was diving into the woods, I glanced around at what could have been several spots where the Northwest Hancock herd path cut over to the 4000-foot mountain top.

I followed what looked quite clearly to me as some light foot travel,

keeping an eye on the ridge line ahead, and frequenting my compass just to be certain. Several times the path that I thought was on began drifting down the side of the ridge, so I turned and began heading toward what should be the crest of the ridge, thinking I might bisect a herd path and continue my Headed up to the top!journey a bit more clearly over to Northwest Hancock. The excitement coursed through me and I quickened my pace to a real, ground-covering trail running pace when I saw a decently beaten down trail in front – I took off down the path! My guess would be that roughly a quarter mile had passed, the topography did not match what I expected to be traversing at that point. Out came the map, checked where I was – and to my surprise – I had hit the trail and was now heading over to South Hancock, along the bowl-shaped ridge line – it’s no wonder that the trail was so well beaten down and smooth going!

As I neared South, the wind gusts picked up just as they always had, beads of sweat turned my running shirt into a drippy, chilly mess! Back down I began, moments later met up with the junction where I began climbing about an hour earlier. I decided to take a quick run-down the intersecting Cedar Brook Trail in search of the Cedar Slide that would lead me to Northwest’s summit. For a brief moment I caught a glimpse of the slide, but in the early Autumnal forest, quickly lost the sight of NW Hancock and decided today was just not my day for standing on this summit that I sought after so badly.

I retreated with my tail behind my legs, gently running and hopping rock to rock over the wet low-land trail.

I returned to the Subaru where I left it at the trailhead and voraciously devoured some cashews and apples as I cooled down, stretched the muscles out one last time, check my phone to text Ciara of my early return trip home – No Service; Trail running down the Osceola Trailshifted into first gear and I was gone – as a line of vehicles tried to grab my parking spot to begin their late morning hike in the Hancocks.

“Headed home” I texted,

“Already?” replied Ciara

“I guess so, I didn’t make it”

“But.. it’s so early!”

“I could go take a drive down Tripoli Rd”

“Go for it!” I read her message with youthful enthusiasm!

Tripoli Road, which is usually gated and closed in the wintertime was now a bustling sub-community with tents popped up on either side of the road, every campsite filled with folks trying to escape the city-life with their family, hikers of all ages – some readying their gear, some unpacking after just finishing their early morning ascents.

I decided to try another peak that had been muddling around in the back of my mind for the preceding several weeks: West over to Middle Osceola! I had done the traditional route East Osceola over to Mount Osceola via the chimney climb (it was late winter, bluebird day, early with no traffic on the trail – another hike in the Whites that I absolutely did not want to end!!), and on another occasion Ciara, Boone, Crockett and I had departed Tripoli Road and ascended the namesake trail to Mount Osceola for sunrise through a thunderstorm,

incredible to be watching lightening from a mountain – while not advisable, we still had a blast!

Joining 5 or 6 other cars in the almost-empty East Pond trailhead. Luckily my vest was still stocked with Muir Energy packets, with a quick top-off of my soft water bottles, I hit the trail as more cars pulled into the lot – I wanted to break out, up the trail quickly before I had noisy kids on my heels – just in case they happened to have any kids, I was there for my peace and quiet!

Headed up the bushwhack to West OsceolaWith already nearly 14 miles logged onto my legs for the day, I huffed my way up the gradual 1,200 foot ascent past hordes of fisher-folk down at East Pond. With views of the Breadtray Ridge off to my right (east), and now assuming I would be cutting over that direction via the herd path that I had read at about any moment; I crested my ascent and ran into a couple up vacationing from Boston and now having a liquid lunch of Sam Adams (complete with stashable silicone pint glasses!). We talked for a bit as I consulted my map and noticed my spur path should be coming through and heading east right about where I was standing.

I wished them well and headed up the path, noting no trail work that I would want to head east into the forest on – back into their direction I went, greeted them once again and wished them a lovely hike. Finally, where I thought my path should be, I just simply swung into the woods and continued walking. I had about a quarter of a mile and several hundred feet of elevation gain behind me as the forest grew thick! Being alone and Ciara barely having a brief run-down of where I was located in the White Mountains, I decided to head back and defer my trek into the unknown until another day – perhaps in winter when the going may be easier.

I was almost merged back up with the East Pond Trail to retrace my steps to my car for the last time of the day, I heard a fair amount of commotion in the woods, it was clearly not coming from traffic on a main trail! I greeted and said “hello!”, my attempts to not startle what could be possible hunters – it turned out to be the mid-aged couple who pulled into the East Pond lot as I made my exit onto the trail about an hour ago!

We talked for a minute – they asked where I was coming from, if I had made the summit of West Osceola;

I explained my predicament and desire to not die alone in the forest on a holiday weekend.

Turns out the husband (I will call them Mickey and Gwen for the sake of my memory failing me) had hiked all these long-forgotten 4000 footers about 25 years ago with some college buddies, but had not been back in the White Mountains in over a decade.

I had to ask if they would mind an extra set of legs joining them for an afternoon bushwhack – they were fully accepting and completely enthused at the thought of a third member to break through the thick undergrowth! Off we went, past the spot The author with new friends: Gwen & Mickey!where I had made the call to retreat and we kept going. Old downed logs simply crumbled under our footsteps, even as we tried to tread lightly through the forest – every attempt to preserve the natural beauty for the next visitors! The trail was gradually steep, especially having to duck under branches or up and over logs constantly.

Gwen took a stray branch to the face and now had a trickle of blood down her cheek,

after we all verified that she was okay to go on – I thought the blood streaks made us subconsciously more tough than we actually were! It didn’t take long before we crested over the ridge and onto the first of many excellent views: the first false summit of the day!

Basically all Mickey did for navigation was to keep climbing with a general idea of where we needed to head to hit at the top of the hill – which actually worked very well, only 1 spot was super thick with evergreens that poked at ankles and tried to reach into our eyes with every step. We survived though, made the 4114-foot summit with several minor scratches, some dirty legs, and all of us completely stoked and riding the “Happy Hiker High” that we had all just signed our names in the Summit Canistersummit register – a real brown glass canister hanging from a long tree atop the highest bit of land on West Osceola.

We made our climb up West Osceola that day.

Well now that we were up in the middle of the forest with no cell service, the only way that we knew to proceed was following the now easy-to-follow herd path which skirted along the tail of the Scar Ridge line and would take us to our next destination: Middle Osceola.

This was a short, quick trek through the col after we stopped on a rocky outcrop to take some photos and soak in the vantage point of a popular mountain range from a location very few knew about – we were so excited to have ran into each other today! The conversations ran high as we got to know one another, comparing the hikes that each of us had done in the past – and everything else that got us to the place we were at that time. They even requested that their new stranger friend join them for a summit-selfie after we made the successful ascent –

it was a genuinely good day to be in the woods with new friends!

Middle Osceola was a bit less remarkable, I searched briefly at the visible summit in search of another
summit canister of the day – however, we would not be that lucky to have two in one day. We were still following a clearly somewhat traveled pathway through the mountain tops, it became overgrown occasionally, forcing us to slow down, look around and shoot (almost blindly, but we three were proving to be decent bushwhackers indeed!) for a lucky direction to meet up with our herd path – which worked every time, luckily!

Onward we went, congratulating ourselves once again for our second successful Trailwright peak of the day! Next stop: Mount Osceola. The path we continued to follow had an old phone line skirting along the sides of the trail, crossing several times and almost snagging an ankle as we passed over top! We all speculated as to what this ancient cable could have gone to (fire tower Morse code cable perhaps?). We reached the end of the phone cable just as the trail broke out at a junction Mount Osceolathat I had clearly recalled from our hike up the Mount Osceola Trail several weeks prior – we were only feet from the high summit rocks of Mount Osceola.

Mickey and Gwen stood anxiously at the intersection, waiting for me to follow to the peak for some afternoon sun basking with them; I kindly declined and told them I was ready to make my descent for my long drive home to a lovely lady, two puppy dogs, and my cat waiting at home for me. During the entire 5 miles back down to Tripoli Road, I passed by countless parties of hikers still making their climb slowly ever upward. I was full-on sprinting down the trail now, hopping boulders, hands engaged as if I could hear Ciara exclaiming “Parkour!” at each marvelous leap that I made.

I completely enjoyed my trail run out to the Mount Osceola Trailhead, all I had now was the 1.6 mile run down Tripoli Road back to the place where I had begun several hours earlier.

Four hours and just under 9 miles further logged and I had redeemed my day in the mountains, completely glowing with enthusiasm and beyond ready to return home for a lunch of dairy-free nicecream made with bananas, frozen blueberries, maca powder, and all the raw nut toppings that I could find in our pantry!

Another epic day playing in the mountains!!

With a combined total for the day of 22.5 miles with over 6350′ of elevation gain later, my legs were ready to cool down, stretch out the stiffening from the hour and a half drive home and plan my next big adventure!

Thanks so much for joining me for my bushwhack over West and Middle Osceola!

Don’t forget to subscribe (over in the right column ->) to receive email invites to my next big adventure!

Great adventures & Happy trails!!

Topo map track


Overall stats for the day:

Recorded with the Ramblr app

  • 8.7 miles
  • 3hr 56minutes
  • 2794′ elevation gain
  • West Osceola – 4114′
  • Middle Osceola – 4200′

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