On Memorial Day 2009, I decided to go on an afternoon hike to the Palenville Overlook, along the old Catskill Mountain House Road, which was used for horse and buggies during the era of that great mountain house prior to the installation of the inclined railroad and later automobile.

The first part of the trail is a moderately steep old wagon road that climbs about 1,000 feet to the site of the Halfway House / Rip Van Winkle Hollow. If it wasn’t gated closed, it would be passable by an automobile. When you reach the ruins of the Halfway House, there are horse tie-downs and ruins of the old tavern known as the Half Way House. It’s where passengers could get a good strong drink and so could horses, as they made their way up to the Mountain House.

After this nice place for resting, the trail climbs a bit more and becomes a lot less steep. You pass by a private hunting cabin, and finally into the forest preserve. You arrive at a pinic area with nice views of the valley, a picnic table, horse tie-downs, and a fireplace full of trash.

From there the trail gently goes up, with two big switchbacks. The trail to the Palenville Overlook switch-backs down about 100 feet off the old Catskill Mountain House Road, and then winds on a narrow trail about another mile to the Palenville Overlook.

You then cross the ruins of the old inclined Otis Railroad tracks, in which all that remains are foundations. According to “AMC’s Best Day Hikes in the Catskills”, the rails and other scrap metal was sold to the War Department during World War I. By then the automobile had made this mode of obsolete as the old horse trail up the valley. All that remains is the cut on mountain, where a high-tension power wire runs.

You eventually reach the Palenville Overlook. The views are amazing, although it was fairly hazy the day I went there. There are awesome stone-built chairs out of old Palenville Mountain House ruins, that provide a great place to sit with a book, as you enjoy views of the Hudson Valley looking south-east. There is another view along the escarpment of the valley somewhat to the north, that gives more due-east views.

From there, I hiked back to the old Catskill Mountain House road, and up to the site of the old Catskill Mountain House ruins. I took some pictures, and then started down the mountain, when I realized I had left my hat up the Catskill Mountain House site. So I ended up backtracking, and ended up missing Memorial Day dinner at my parents house. But so be it.