Miles: 1396.1 | A morning of relentless rain at Island Pond delays our start, but once the storm breaks we head straight into New Jersey’s iconic challenges. The Lemon Squeezer tests our nerves and creativity, followed by water cache miracles, blueberry grazing, and the decision to avoid crowded Bear Mountain. Camping high on Black Mountain rewards us with hazy views of the New York City skyline—but the exposed summit, dropping temperatures, missing sleeping bag, and booming late-night music from the valley below make for a restless, shivering night before dawn.
In the morning I awoke by Island Pond at 5am. It was pouring rain. Some of the strongest I'd seen since Georgia. The area around my tent quickly started flooding and my tent walls began sagging. The condensation was awful.
I quickly packed up what I had inside my tent to keep it dry and just lay on the bare tent floor leaning against my pack. I didn't want to get up in this rain. The forecast said it should pass by 9am. Miles agreed to wait it out.

The Lemon Squeezer itself actually wasn't so bad! It was the little rock climb after it that was truly formidable.

By 11am it finally stopped. I thought the rain would reduce the heat and humidity but it only got hotter. We left camp at noon and headed toward the next big thing: Bear Mountain and the Trailside Zoo. Right after we departed form Island Pond we came upon the latest, rocky challenge: The Lemon Squeezer.

Miles went first and had a hard time. There were no foot holds. He took off his pack and chucked his poles up to the top of the climb.
Once he was up it was my turn. I tried to keep my pack on but it effected my balance too much. I took it off and handed it up to Miles. I'm shorter than Miles and he barely found a place to put his feet for leverage. There was no way I could use my legs to hoist me up. As far as I could remember my arms were pretty weak. I tried to pull myself up but I couldn't reach the hand hold he used. I tried again: no luck.
For my third try I decide to ignore what Miles had done and just try to do it my way. This time, with a groan, I hoisted myself up. I banged my elbow in the process, but I made it!
Once we got past the lemon squeezer it was pretty smooth sailing. We walked through some hilly, grassy areas where we saw a few tourists. At some town water towers we found a huge water cache. Both of us were hungrier than usual so we decided to sit and make some food. After that, we passed a few water caches (thanks to some local trail angels) and stayed hydrated!
I checked further ahead on Guthook. We couldn't really camp on Bear Mountain but it looked like the day we hiked Bear Mountain (a tourist trap of a park) would be overwhelming, possibly crowded, and we couldn't really plan for how long it would take. I saw some comments suggesting that up to five tents could fit on top of Black Mountain, the peak right before Bear Mountain. We decided to risk it and try to camp up there. Reviews about the views from Black Mountain were great, too.


It was incredible, by the New York Long Trail we were about 54 miles away from the edge of the city. As the crow flies probably 30 miles. But we could see the skyline all the way out here! Miles and I pitched our tents separately.
As we hiked we passed tons of blueberry bushes and we snacked on them as we made our way up to the peak. At the top we were rewarded with hazy views of New York City!


At this time I didn't have a sleeping bag because I had to send mine home in Warwick. There was an issue with the way it was cleaned and the feathers wouldn't stay in the baffles properly any more. It wasn't really keeping me warm. I thought I might be okay with just my liner because it had been so hot. There was a new sleeping bag waiting for me, along with my parents in Pawling. Apparently, the rain did take away some of the heat. We also didn't consider that we were camping at a higher altitude than normal with little tree cover to block wind.
Miles lent me his puffy jacket and I wore it over my legs to keep me warm. I wore every item of clothing I had: wool base layers, my jacket, my rain coat, everything. Eventually, as the sun went down it started to get colder. Much colder than I had expected. Down into the 50's it went. It's crazy that such a high number can be so cold! Anyway, I was cold all night. I didn't sleep much.
Around 10pm I started hearing noise. Music noise. It almost sounded like a concert when song after song sounded like the same artist and style. The music echoed over the peak from the valley. At first, I had thought maybe it was someone else camping nearby. Once I heard the echo I knew it couldn't be.
It sounded like it was coming from at least a quarter mile away. It was so loud I could hear the Spanish lyrics word for word. Every drum beat and symbol hit echoed up to us. I lay there chilly and tired and annoyed. Eventually, around 2am, the music stopped. (The next day when we walked through the park I realized that the park was most certainly the source of the noise.
I finally fell asleep but only for a short while. At 5am tent stakes were being scraped and hikers around me started packing up and talking. I got up, annoyed and stiff from trying to stay warm in fetal position all night. I went to Miles' tent to give him back his jacket and he offered for me to sleep in his sleeping bag for an hour or two if it would help. I took him up on the offer.