Mt. Osceola Loop via Tripoli Rd, Goodrich Rock, & Greeley Ponds (White Mountain National Forest)

Mt. Osceola Loop via Tripoli Rd, Goodrich Rock, & Greeley Ponds (White Mountain National Forest)

Hike Type: Loop

Distance: 15.36 miles

Elevation: 4,032 feet

Time: 7 hours, 26 minutes (6 hours, 27 minutes moving)
Hiking Challenges: 52 Hike Challenge 2025; Terrifying 25, NH Rocks that Rock, Operation Alaska Benchmark Challenge

The Hike 

'Twas the day before my 48/52 Grand Finale and all thoughtout the house... I was not, because I was pregaming it with a longer hike. I was up at 3:00am and out at 3:20am with my sights set on the Osceolas via what one could argue is the least convenient route! It was chilly and clear out in Boston when I left, which was lovely. I got my breakfast sandwich from Hooksett at 4:25am and made it to the Mt. Osceola Trail trailhead at 5:40am. It was in the upper 20s, which felt wonderful, and the skies were still clear. I christened the trailhead bathrooms right on time, and I miraculously had $5 to pay the day use fee! Everything was slightly frosted and glittering in the light of my headlamp - time to start the journey!

[5:52am - Start of Hike on Tripoli Road]

I purposefully started the hike in the dark, as I knew I had an almost 3-mile road walk along Tripoli Road. The plus side of going toward Livermore was that it was almost entirely downhill! There was a slight rise from the Osceola parking lot, but that was it! It alternated between dirt and pavement for much of it's length, slowly trending towards pavement nearer Livermore. I was in my fleece, nano puff, and gloves for much of the downhill walk. I could occasionally make out the silhouettes of Mt. Osceola through the trees - that is, when my foggy breath wasn't clouding my headlamp's vision. 

The sky had it's first light on my walk and slowly began to illuminate the world around me (key word: slowly). A truck passed me slowly on a rough stretch of road, followed by another car in the opposite direction. Around the one mile mark, there was a steeper stretch of road that eventually joined a stream that was paralleling the road. Tripoli Road crossed the stream on a bridge and I later caught a cool early morning tree view to North Tripyramid. The road eventually turned, revealing Middle and South Tripyramids before sending them behind the trees. I finally started to warm up after 30 minutes of walking as the sky began to lighten and the colors remaining on the trees began to show themselves. 

I was able to turn off my headlamp around 6:30am, even though it was still a little dark outside. It was so pretty and peaceful out. I could make out East Osceola through the trees now as my body temperature alternated between warm and cold, and later I would catch the awful scent of the Livermore bathrooms. The forest critters began to wake up around 6:40am as I started to see signage for the Waterville Valley trails. Soon after, I turned left off of Tripoli Road, crossed the brook on a bridge, and landed at the Livermore trailhead! The bathrooms smelled horribly, and I added to the stench with a second christening. There were three frosty cars in the parking lot, and now it was officially time to be in the woods!

[6:45am - Livermore Trailhead]

[6:51am - Livermore Trail]

[6:56am - Livermore Trail/Enters for Protection Area]

I was wearing my waterproof mid-height boots, which were still pretty new. At Livermore, I loosened up the ankles of them for comfort, as I was still figuring out how to best tie them and break them in. I had a bit of rage coming into this weekend from my boss, but I was trying my hardest to not think about it. I got yelled at by my first squirrel du jour at 6:52am, and I enjoyed all of the frost at the Depot Camp before crossing the bridge and turning onto the Greeley Ponds Trail.

[6:59am - Greeley Ponds Trail]

This turn signaled a delightful ramble for the next few hours. The Greeley Ponds Trail followed another road that was wide and tree-lined, now with conifers for the time being. According to the guidebook, this stretch of trail was severely damaged after Tropical Storm Irene, so there were a good amount of relocations, but all relocations were simple to follow and continued the road grade. I was surprised to see a large group of hikers in one of the closed sections, presumably eating their breakfast. They were the first and only people I would see for a LONG time! 

I was loving the cold air as I followed the road which gained elevation at easy grades, similar to Lincoln Woods. Eventually, about a mile from the Osceola Trailhead, I took my Nano Puff off and continued my walk. The trail joined the Mad River, which looked particularly beautiful with the remaining foliage. There were a few short spurs to nice views from the river, which was also running low, just before the Goodrich Rock Junction.

[7:21am - Goodrich Rock Trail]

Finally time to gain some elevation (before losing it again)! I took my fleece off once I turned onto the Goodrich Rock Trail - an elective Terrifying 25 trail. The trail was narrower, but still plenty wide (about a sidewalk's width) and began to climb moderately to a few cool boulders in a drainage. At the boulders, the trail turned left and meandered into the woods for a bit. The woods here smelled wonderfully fragrant - similar to the floral smell I noticed going up Flume Slide a couple weeks ago. 

The sun was beginning to shine through the trees as the trail began to climb again. There were small boulders throughout the woods - I thougth these were the "Davis Boulders" - but not yet! Soon after, I made my way to the true boulders, and they were so fun! The Goodrich Rock Trail wiggled through a wide crack in a broken rock and then scrambled through a mini cave (which was fully bypassable). 

Afterwards, the trail continued on a flatter rugged ramble before scrambling down to the base of Goodrich Rock, only to climb up around the far side, which led right to the "terrifying" ladder. The ladder itself wasn't that horrible, but the wood was very smooth and the ladder was just a little shaky. 

[7:50am - Goodrich Rock]

The top of Goodrich Rock was a perfect spot for a break! I got a nice view of Sandwich Dome and Jennings Peak with a peek to Waterville Valley Ski Area and a framed view of Mt. Tecumseh. I took a sit and enjoyed a breakfast sandwich from Hooksett for a few minutes. I originally planned to also take a detour to the Timber Camp Trail, but I was getting my sights set on the Osceolas and wanted to get there sooner, so I was flirting with leaving that trail for another day. I sat up top just long enough so that I got chilly again, and then I was on my way back!

[8:02am - Goodrich Rock Trail]

The return to Greeley Ponds Trail was quick and easy, and felt remarkably faster and shorter than the climb up (which does make sense, in all fairness). I cannot recommend this side trip enough! It was a perfect way to warm up, have some fun scrambling, and to get some views in before I tackled the main peaks of the day.

[8:21am - Greeley Ponds Trail]

Now I was back on the wonderful Greeley Ponds Trail, continuing to slowly climb my way to Mad River Notch. It was chilly back along the river in the shade, and eventually the trail began to climb more... moderately, but still very easily. Eventually, I was high above the river and the sun was lighting up the trees - it was so wonderfully bright and golden - I love fall! I was also grateful for the autumnal tree views - there was truly nothing impressive to see, but it was just nice to have something to look at. I remembered that this stretch of trail is technically a relocation and used to be part of the Timber Camp Trail (implying the Timber Camp Trail used to be much longer), and I officially decided to skip the side trip when I reached the junction.

[8:37am - Greeley Ponds Trail/Timber Camp Trail]

From the Timber Camp Trail junction, the trail began to descend - the change of gears felt nice on the legs. I could occasionally make out a wildly impressive cliff on East Osceola through the trees. The trail hit a switchback and then began to descend perpendicular to the contour, providing a top-of-the-trees view to a shoulder of Mt. Kancamagus. I passed some sort of artifact, I assume a logging remnant, and then I crossed the Mad River on a sparkly, frosty bridge.

[8:47am - Greeley Ponds Trail/Kancamagus Brook Ski Trail]

After the bridge, the Kancamagus Brook Ski Trail turned right as the Greeley Ponds Trail began to climb up and over another hump - another relocation. The trail was still plenty wide, but noticably narrower now. It was also cold again because I was back in the shade! There were better tree views to the East Osceola cliffs on this side of the river, and the trail soon began to descend and zig-zag back down to the original trailbed. 

The closer I got to Mad River Notch, the larger East Osceola became - how am I supposed to climb that? The trail narrowed again down low and I had the pleasure of hiking across a few bridges (I guess this is the perk of the trail corridoor also being an XC Ski trail! The sun soon came back, warming me up, and the trail easily rose to another bridge and more tree views to East Osceola - I was feeling glad that I skipped Timber Camp, because this was great!

[9:02am - Greeley Ponds Ski Trail]

[9:07am - Lower Greeley Pond]

I excitedly entered the Greeley Ponds Scenic Area (at a forest protection area sign) and a junction with the Greeley Ponds Ski Trail, where the ski trail continued straight and the Greeley Ponds Trail turned left and crossed the Mad River. To make up for bailing on the Timber Camp Trail, I did decide to take the Greely Ponds Ski Trail to catch a view of the Lower Pond. The trail felt like a ski trail - horrible, wet footing and a little grown-in, but it was worth it! I crossed a nice bridge and came to an absolutely stunning view of the Lower Greeley Pond and East Osceola (plus a beautiful reflection). There was an illegal campsite just into the woods at the view - boo! I noticed my shins starting to feel splinted on the return trip, so I toyed with how I was tying the boot which may have helped a little?

 

[9:13am - Greeley Ponds Trail]

I easily crossed the Mad River, which was now in the sun, and the Greeley Ponds Trail was rocky and rooty now. There were a few side paths on the right that led to nice views of the ponds, mostly with Mt. Kancamagus towering above. One side path led to a little shady grove with some ice, which was fun! There was basically no foliage left, but it was still so gorgeous. 

I started to catch some spider webs to my face, but I was happy to have made it this far into the hike without any, so I accepted them. I admired some mallards munching on the grasses growing out of the Lower Pond, and the northern end of the Lower Pond was pretty marshy and grown-in.

I followed a guidebook suggestion on a side path along the Upper Greeley Pond and got a wonderful view of the cliffs and slide tracks on East Osceola. I was going to take a break here, but I noticed a comical amount of fresh moose poop, which didn't immediately deter me, but there was basically nowhere to safely put down my pack without landing in poop, so I went back to the Greeley Ponds Trail and found a nice sitting spot for my next break.

[9:40am - Break Along Upper Greeley Pond]

My break was delightful - I sat along the south shore of the Upper Pond. I had more nasty leftover pulled pork BBQ pizza that was 80% BBQ sauce, but the view was delightful. I threw on my windbreaker for the break and stayed just long enough to get cold again. I finally finished my first Nalgene at 3 hours, 58 minutes/9.28 miles, which felt like a problem, but thankfully my pee was mostly clear and I was not cramping!

[9:52am - Greeley Ponds Trail]

I had one last side-path stop at the northern end of the Upper Pond, which had a little beach area, and then I had a nice and easy hike from the Upper Pond to Mad River Notch, crossing the headwaters of the Mad River on a slightly sketchy log bridge and scooting around a neat boulder. After the boulder, there was a duck-under blowdown and then the Greeley Ponds Trail veered left while the Greeley Ponds XC Ski Trail veered right, and then it was the height-of-land! I did a quick potty break and dumped a TON of trail debris out of my boot here. It was time to actually climb!

[10:06am - Mt. Osceola Trail]

From the trail junction, I turned left onto the Mt. Osceola Trail. The sign comically said 1.5 miles to East Peak and 2.5 to the main peak, which felt crazy, as I'd been hiking all day and barely climbed anything! The Mt. Osceola quickly left the Greeley Ponds Scenic Area. The Notch proper was very pretty and open with the fallen leaves, and I preventatively took off the windbreaker. 

The climb started right away, transitioning quickly from east to moderate grades with rocky footing. My lungs were already feeling spicy due to the physical exertion in cold weather, but I kept telling myself "you're fine!" I could occasionally hear a loud car on the Kanc, but otherwise it was very quiet. The semi-open hardwood forest was really pretty, and it was transition to spooky once in the conifers. There was a walking break area that was spooky, rocky, mossy, wet, and really neat. I'm guessing the boulders that littered the woods fell from the towering cliffs above at some point in the past?

There were a solid amount of stone steps for a famously rough trail. I caught a few tree views to the cliffs above, and more boulders were near the trail. Sadly, the trail went around and not through the boulders. Not including the group I saw at the start of the Greeley Ponds Trail early this morning, I saw my first people of the day at 4 hours, 41 minutes/10.52 miles - nice!

The climb steepened again, but it wasn't overly ridiculous. I was a little nervous about the temperature paired with the amount that I was sweating, but that felt like a later problem. The trail began to deteroriate in terms of erosion, but it wasn't TOO awful. I crossed paths with another person as the trail yet again steepend and passed a neat slab just off-trail (no view). From here, the trail steeply climbed along a rockier and sketchier stretch, but I caught a little view to the Tripyramids from here, which was fun!

The steepness continued as I began to hear people down below. I hiked through a steep, wet, eroded area, then another with just a short reprive between the two, but then I arrived at the bottom of an old slide track that had a wonderful view of the Hancocks, Jefferson, Carrigain, Carter Dome, and Stairs Mountain, to just name a few. 

I scrambled up the slide track (not sketchy), passed some ice patches, and stomped on my first needle ice of the season!

The trail was back to being super steep, eventually leading to a "washed out gully," which was kind of like a mini-chimney - fun! The Mt. Osceola Trail gets MUCH easier from this point, rounding a shoulder and turning left. A spur to view on the right led to an absolutely sick view of East Osceola, Mt. Osceola, Moosilauke, the Kinsmans, the Franconia Ridge, Garfield, and Owl's Head, with more to see, too. Just amazing!

Now I was hiking along the spine of the ridge and it was simply lovely. For the sake of my body temperature, I planned to blast through East Osceola and do my last big break on the main peak. The final push to East Osceola was moderate with one annoying blowdown that was neither easy to go over or under. All of the wet spots were ice near the summit, but thankfully there weren't that many. I did throw my rock spikes in my pack, just in case. A side path on the left near the top led to a grown-in view, and there were many new and old blowdowns near the top (but not blocking the trail).

[11:18am - Mt. Osceola Trail/East Osceola Summit]

It was fun to be back on this viewless summit for the first time in over five years! I truly just got my photo and blasted off. It was nice and sunny up on the ridge, but the descent of the summit was chilly in the shade with some more ice. The descent was rough, but I was happy to be using different muscles again. There would be occasional peekaviews over to Waterville Valley - I was still surprised how early peak foliage was this year! Further down, I passed another on-trail excellent view over towards the Pemigewasset Wilderness, along with two more people. It was fun to see the full Pemi Loop cirque!

The woods were lovely as I descended to the col, and the climb from the col started dramatically with the famous chimney! I forgot how fun it was to climb it! It's all the fun of any steep scramble, but with excellent hand holds. It felt much bigger the first time I climbed it, though! I giggled that the trail blaze was simply an arrow that pointed straight up.

From the top of the chimney, I caught a nice view back to East Osceola and over to the Tripyramids. I dipped back into the trees, which smelled of wonderful pine needles with some needle ice on the ground. The trail transitioned from lovely to gravelley and eroded, which... was expected. The trail climbed more moderately as I reflected on this push almost killing me those five years ago - I wasn't feeling 100%, but I had already been hiking for 12 miles and over 6 hours, so I think I was doing fine!

I caught some more good views from the top of the steepest part of the climb and crossed paths with person #6. A walking break gave my legs a nice break as I traversed a height-of-land before slightly descending and seeing a RUDE view up to the main peak of Mt. Osceola. 

I knew I was getting close when I crossed paths with human #7 who was in cargo shorts, cotton hoodie, and no pack. There were a few more icy pushes along this final push, and soon I was up on the beautiful open summit! 

[11:55am - Mt. Osceoa Trail/Mt. Osceola Summit]

I've been saying this every time I've repeated a hike, basically - I love seeing these views with such a deeper knowledge and context of these mountains! The summit wasn't crowded, but there were at least 10 other people, including a couple families and one guy on a loud phone call. I found the USGS disc, took a few photos, and then stood there wondering if I wanted to stay or not. I opted to stay, which was objectively the right move - I had just gotten used to being alone! I had another bad slice of pizza as I enjoyed the view - specifically of the North Tripyramid slide, Chocorua and the Sisters, and Lake Winnipesaukee. 

[12:09pm - Mt. Osceola Trail]

I noticed that the families were starting to pack up, so I packed up faster to get ahead of them. There's lot of side/spur/herd paths around the summit, but the only one detailed in the guidebook is from the older fire tower footings (not the ones at the main view, the ones directly on the trail) - I turned right to catch a view of... basically nothing, it was almost entirely grown in. 

I continued my blast-off down the trail, which had some standing water and ice and slippery slabs. I gave up counting people on this descent, as there were MANY folks ascending (not a stupid amount, but definitely enough). I passed the herd path to Middle Osceola, which is very intriguing to me, but for a different day. I suffered through the seemingly endless slabs (I have rough memories of navigating them five years ago in my beat-up sketchers - I was doing better today!). I started to catch up to and pass many folks, some of which were French Canadian, and I crossed paths with a group of six college-aged kids that were very funny. They came up to a slab, all groaned, and one of the girls yelled "I DON'T EVEN LIKE HIKING. THANKS A LOT, WILL!" which made me giggle.

My brain turned off for a while as I continued my descent - every time I stopped to take a photo or write a note my body reminded me of how badly I needed to pee, but I was waiting for the pathroom at the trailhead. The grade mellowed out when my watch hit 15 miles on the dot, which would have been welcomed, but the trail was so rocky it was almost easier to be descending with gravity on my side!

[1:12pm - Mt. Osceola Trail/Enters Forest Protection Area]

The temperature felt delightful now that I was down low, and I knew hope was on the horizon once I entered the Forest Protection Area around the trailhead! The character of the woods changed, and suddenly, I was back!

[1:18pm - End of Hike]

After my hike, I used the bathroom and changed and enjoyed my last piece of sad pizza at the picnic table right at the trailhead. I was in flip flops, shorts, and a t-shirt, and only later realized it was a toasty 49 degrees out. I had a shockingly painless drive home and giggled at the SUCKERS driving north during rush hour for the long weekend (I was actually the sucker, as I'd be doing the drive at 3am tomorrow morning). My grand finale hike is tomorrow!

Step-by-Step

- Park at Mt. Osceola Trailhead ($5 Day Use Fee).

- Start hike by turning left onto Tripoli Road.

- At Livermore Trailhead, turn left onto Livermore Trail.

- At jct., turn left onto Greeley Ponds Trail.

- At jct., turn left onto Goodrich Rock Trail.

- At Goodrich Rock, turn around.

- At jct., turn left onto Greeley Ponds Trail.

- At Forest Protection Area, follow Ski Trail to Lower Greeley Pond.

- At Lower Greeley Pond, turn around.

- At jct, turn right onto Greeley Ponds Trail.

- Take spurs to views of pond.

- At Mad River Notch, turn left onto Mt. Osceola Trail.

- Summit East Osceola, continue on Mt. Osceola Trail.

- Summit Mt. Osceola, continue on Mt. Osceola Trail.

- Follow Mt. Osceola Trail back to car.

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