We signed in at the trailhead at 9:34. The forecast called for rain early with a break mid-day, then more rain starting in the early evening. Knowing this, I finally bought a hiking poncho which advertised a wider back to facilitate up to an 80L pack. It worked as advertised. I was also very excited to put my 3-season boots back on. They aren't more or less comfortable; I was just happy for the change of seasons.
Road Walk
There are loads of herd paths leading away from the trail. I followed a couple of them to see if they went anywhere. I'd heard that there is airplane wreckage on this mountain, but I hadn't bothered to research that fully. From what I can tell from searches, the wreckage is closer to Kaaterskill High Peak.
As we gained altitude, our leisurely walk was wreathed in fog. We met several people on this stretch who we tried to chat up. One hiker said she comes to Overlook with a group of friends every Monday and she said she's never spotted a snake. This surprised me a great deal. However, two other couples I met confirmed they see them at the summit a lot. I suspect it all depends on the time of day and weather.
Overlook Mountain House
Atlas Obscura has a great history of the Overlook Hotel in all of its iterations. Apparently the ruins here are the third attempt to build the hotel after the first two burned to the ground. Fortunately, after this version caught fire, the concrete remained and provided hikers an interesting landmark to explore. According to every resource I've found, visitors should absolutely beware of rattlesnakes in the ruins themselves.
We peered into exposed basement of one of the outbuildings. I suspect it was the chapel which was discussed on the Atlas Obscura site. I think Quinn would have a blast here. I may bring him in the Winter.
Be careful of broken glass near these buildings. A lot of it is weathered and/or crushed flat, but you should still be cautious of our furry friends' feet.
The Summit
...and more picnic tables. I can see why this is a popular place to hike. It's a quick, easy hike with a summit that usually has gorgeous views and great amenities. Still, every source warns that the space under the tower is a favorite spot for the rattlesnakes to lounge.
We took a few minutes to sit, relax, and eat a snack. It was windy, but warm. We picked up some litter that was lying around before heading back down to the car. We were shadowed by a creepy, loud flock of sparrows on the way down, but we were fortunately not carried away by them.
Back at the Trailhead
We signed out at 12:09pm. By the time we reached the trailhead, it was sunny out and I was sweating. All the other hikers we met heading up the trail would enjoy an incredible view of the surrounding area.
There is a huge Buddhist temple accross the street. On our way out we passed several other Buddhist and Tibetan buildings. I know most Buddhist temples are very tolerant of vistors, but I chose to move on. We had another mountain to climb, after all. Mount Tremper was nearby and also known for rattlesnakes, so I was motivated for us to claim it early.