Overlook Mountain near Woodstock, NY - The Catskills

This week, I finally decided to take the long trip (about 2 and 1/2 hours) up to the Catskills and had fully hoped to hike the approximately 9-mile North Point trail to Stoppel Point. This plane crash site that I have been wanting to see was the objective and I was prepared to put in the hard work. Although I did make use of my Catskills Region map, the plane crash site still eludes me.

I woke up at 4:45AM, leaving myself some extra time as I knew this drive would be nearly twice as long as usual. The conditions for the trip seemed just right: 40-degree temperatures and a partly cloudy sky. With my pack stocked up the night before, I was able to eat a small bowl of cereal and head out the door.

At this early hour, the sky was in all of its darkest glory and sunrise was still hours away. I had planned to find a place to eat breakfast a little closer to my destination to avoid any traffic, but I didn't pick a specific eatery.

After my obligatory stop at Dunkin' Donuts, it was onto the highway. There was nothing to see but black on either side of the road and it went on this way for some time.

About an hour into the trip, I stopped at a rest stop to get some more coffee and some cash for the tolls. Almost pathetically, I was ecstatic to find a rack stocked full of magazines and brochures on many of the region's state parks and attractions. Generally, this would not be at all exciting, but each of the free booklets featured wonderful maps, and so I left with a thick stack. Again, I will describe my elation as "almost pathetic".

It was another 30 minutes or so before the sun came up and I was able to see what was around me. I was definitely where I wanted to be. Despite the substantial clouds hanging above, I could see blue sky peeking out in some spots and a beautiful mountainous landscape in the distance. However, one thing I was able to now see made me slightly uncomfortable about my plans. There was a good amount of snow on every surface except for the road.

Even though the temperatures were hovering around 40 or 50 degrees for about a week since the last snowfall and all of the snow near my home promptly melted, up here in the Catskills, the snow remained. Evidently, this region got more snow than I had realized and it had not yet melted. I pulled off to the side of the road and reconsidered my plans. If I was out searching for a crashed plane that is located somewhere off of a nearly 10-mile trail, the snow would definitely make this more difficult, if not impossible.

I pulled up the trusty Alltrails app and searched for an acceptable alternative. The top-rated hike in the Catskills was listed as Overlook Mountain, which included a steep and steady 1300-foot climb, hotel ruins, a fire tower, and an amazing scenic view at the end. Although it was an out & back trail instead of a loop and 4 and a half miles instead of 9 and a half, it seemed like it would suffice, especially with the snow on the ground. So, I adjusted my GPS and got back on the road.

I found myself pulling off on the side of the road again not more than 15 minutes later. I had searched for "diner near me" on Google and was shown only a few, scattered options, all which seemed like lunch bistros and none which would open until 9AM. This was a surprise to me. No matter where I had driven in the past, I had always been welcomed by a long list of diners, 3 or 4 within a few miles in some cases. I knew I needed to eat a good breakfast and found myself failed by technology. I needed to find a place the old-fashioned way; I needed to ask an actual human being.

The Stewart's Shop was one of the listings on my phone although it appeared to be more of a convenience store than a diner, but it was open early. I entered the store, a nice, clean establishment with two older women working. I glanced around for something that might cover breakfast, but quickly realized that the closest thing I would be able to eat would be a buttered roll or a doughnut. I asked one of the women where I could find breakfast and both responded, in unison, "The Pine View".

I was surprised that the Pine View Diner did not appear when I did my search but the directions were easy to follow and the place was close by. I was pulling into a small parking lot in front of the diner within minutes of leaving the old women and was happy to see a sign hanging on the wall outside, "Hunters Welcome: Open Early". The word "Hunters" could easily be replaced by "Hikers" and so I entered.

The diner appeared to be no more than a re-purposed living room on the first level or a two-family home. A counter stretched along the length of the room and a sole man wearing work boots and a hoodie sat stirring his coffee and staring at his cellphone. I sat down and ordered myself my usual breakfast (bacon, a short stack of pancakes, and one egg over easy). The man behind the counter was just friendly enough and the food was delicious.

While I ate, a few other men entered: one NY state trooper, another middle-aged man wearing work boots and a hoodie, and a third man who resembled Santa Claus. Everybody knew the man behind the counter by name and he knew all of them by theirs. I joined in on some of their conversations about current events and each time they seemed surprised that I could speak, but welcomed me into their discussion. When I left they all wished me a nice day and I reciprocated. I get a slight sense of satisfaction from being a stranger in a faraway place. I am sure that when I walked out the door somebody sitting at the counter looked at the others and asked, "who the hell was that?"

The trailhead is located in Woodstock and so I had the fortune of driving through the sleepy-looking, little town that has clearly never gotten past that famous 1969 concert. There are many buildings in town (including records stores, thrift shops, and art galleries) that have signs promoting peace and love, many peace signs adorn doors of houses, and even the grammar school marquee reads "Peace, Love, Education".

I arrived at the trail and was surprised to see two other cars in the lot parked over a slick, packed-down snow sheet. This snow sheet continued right onto the trail. The trail is actually more like a rocky road up the mountain as it is quite wide throughout.

Early on, I looked down to find that I was standing right in the center of a long sheet of ice that was hiding under a dusting of snow. I didn't move for a moment, I needed to carefully plan my next step. I intended on using my trekking poles to shift myself to the right about 2 feet onto a few inches of snow at the edge of the ice sheet, but as soon as I moved my right arm I began to slide, quite gracefully, backward about 6 feet.

Surprisingly, I didn't fall on my ass. Once I was safely off of the ice, I moved onto the snow and continued my ascent up the mountain. I found it easiest to move through the thickest stacks of snow for traction. The surrounding woods were crowded by leafless trees. From time to time a tree with shriveled, brown leaves would stand out among the other trunks.

A little over a mile into the hike, an apparent side trail opened up to the right which I followed. I found nothing but a radio tower and a small shack and made my way back to the main trail. When I arrived back at the junction, I was surprised to see another hiker, presumably one of the other people who had parked in the lot, about 100 yards ahead. He was moving ever so slowly up the trail, like a tortoise. It had started to hail so I pulled my hood over my head.

I took some time to take pictures and take in my surroundings as I let the other hiker move a little further ahead. I like hiking alone or with friends and cannot stand tailing strangers for miles and miles. After a few minutes I continued. I was increasingly dismayed to be following a power line further and further up the mountain. I so enjoy seclusion and remoteness that I become very uncomfortable, almost angry, when signs of reality creep into my hike.

The trail carried on as a white, slippery, steep, continuous ascent for another mile or so before it leveled out. I was excited when, about 100 yards ahead, I could make out windows and an arched doorway. I was looking at the abandoned hotel ruins that I had read about. The hotel was originally built in the first half of the 1800's. It struggled to attract guests and suffered 2 separate fires before closing down in 1921. New ownership planned to rebuild and renovate, but they gave up after some time and sold the property to the state. Even thereafter, the hotel saw 2 more fires, most recently in 1970.

There is the actual hotel, a lodge, and a few other foundations for other buildings that were never built in this area. As you hike, the path leads right to the fountain outside of the entrance of the hotel. There is a stairway to a non-existent second floor and a beautiful, elaborate fireplace against the back wall. I made my way to the lodge behind the hotel and found the floor had completely disappeared. Upon entry, there is a 10-foot drop into a snow-filled (or grassy in different seasons) basement. The hailing subsided and light flurries replaced the pelting ice.

However, I was again dismayed to find another telecommunication tower and a small, fenced-in shack behind the lodge. Again, reality was infecting my hike, but I brushed it off since I was happy to see it marked the end of the power line. A sign a few feet away read "Fire Tower" over a yellow arrow. The tower was visible from the trail, looming atop the mountain. To my right, I could start to make out the expanse through the trees. Lakes, farms, and buildings were starting to become visible. The tortoise hiker was coming back down towards me and advised me it was colder up at the top and that the wind was whipping.

I went up a small hill and came to a cabin and a privy. The fire tower was behind me and another sign indicated a "Scenic View" was ahead of me, beyond the cabin. It was only a short distance before I came out through the trees an onto the edge of the cliff. The view was absolutely breathtaking. Even though it was cloudy, I could see for miles. I haven't had such a long view since I hiked in Shenandoah National Park in Virginia. A field below had a peace sign, big enough for me to see from my elevation, dug into the earth.

In the distance, the clouds began to split, allowing very prominent sun rays to break through to the world below. The surface of the lake began to glimmer in the distance. To my right, a billowing, misty cloud clung to the ridges. At this point, the snow came down harder and faster and the wind picked up. I spent some time at the top of this mountain contemplating. This is why I hiked, to see things like this and to let this amazing vista clear my mind.

With the wind and snow, the mist that stood in place just moments before began to float across my eye line and blocked out the view. I'm glad I made it to this outlook when I did, otherwise I may have welcomed by a wall of white and could have totally missed out on this amazing sight. With the view gone, I hurried back to the fire tower, hoping I would be able to climb up over the clouds for an alternative view.

When I reached the fire tower, only about 100 yards from the vista, the wind had picked up and it was blowing violently now. With trepidation, I began to scale the steps of the tower. Every inch of each step was covered in ice and the open spaces in the protective fence had been catching shards of ice as well. With each level, the wind became stronger and stronger and louder and louder. I looked upward each time I reached the top of a flight of stairs, hoping that, somehow, I was suddenly at the top.

About two levels below the top I paused. The wind was really strong up here and the entire structure was quivering. I retreated down one level. I needed to compose myself before going to the top. I advised myself to "not be a pussy", put my head down, and rushed to the top. Unfortunately, the hatch to the actual enclosed space at the top of the tower had been locked and so I had to take in the view from within the stairway, the view obstructed by beams and fencing.

However, at this moment, the wind started to die down, it stopped snowing, and the clouds in the sky to my right started to move. Slowly, but surely, the clouds opened up over what had just previously been nothing to see, and left me with an amazing view of the distant mountaintops. Blue began to overtake the skies and the sun started to shine through the trees. I had a leisurely descent down the mountain the way I came, much easier than the way up. The sun shone down over my shoulder through the trees and I returned to my car by lunchtime.

Overall, I enjoyed this hike for the fact that it was continuously strenuous and sufficed as a good workout. The views from the top also helped make this hike worth it, but I wonder how disappointed I would have been had the weather not cleared up or if I would have gotten a view of nothing but clouds, but I was fortunate. The hotel ruins were also a big plus as I always like to have something interesting to explore on a hike.

However, the power lines and telecommunication towers did shatter my sense of seclusion and the trail itself was a bit mundane. Perhaps, if it were a different season, the evident lushness of the forest might make the trail both more visually stimulating and increase the level of perceived remoteness. If I do choose to return to this hike's vista and to the hotel ruins, I will likely hike the Devil's Path and approach from the North.




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