Overlook Mountain

An Outdoor Adventure

By Tom O’Grady

Mother’s Day 2018 saw us headed south along NY Route 32 to Overlook Mountain in Woodstock. To date, we had only completed mountains in the Adirondacks on our fire tower adventures and Overlook would be our first fire tower in the Catskills. With any luck we were hoping to successfully reach the summit on this trip. Our first attempt at Overlook coincided with Easter on the last weekend in March. On that trip, the ice and slush proved difficult for the kids, and we cut it short. Today we were better prepared and armed with nicer weather! 

Upon arriving at the trailhead, across from the Tibetan monastery, we noticed that many other people had to hike and had gotten an earlier start. There was no space left but it was great to see so many people out hiking on Mother’s Day! Luckily, the NYS DEC responded to the popularity of Overlook Mountain by putting in an additional trailhead and an overflow parking lot, approximately a half-mile down the road. To save time I dropped everyone off at the main trailhead and headed solo to the overflow lot. Be careful on the way down to the newer trailhead to avoid parking in what looks like an overflow lot. This is actually space owned by the monastery. I was the first to park in the overflow lot and jogged up the newly cut trail to meet everyone at the trailhead proper.

Prior to allowing the kids to look for a walking stick we went over some quick additional guidelines for this trip. Overlook is a tremendous mountain with a lot to offer. And it is especially easy to get caught up in the moment of exploring, particularly near the top. But on this hike, we warned that it was particularly important to be aware of your surroundings, stay near an adult, and not go off the trail. Overlook also has a population of timber rattlesnakes that den in the ledges near the summit. Because they den from about November to April it was possible that we would encounter some. Timber Rattlesnakes are not particularly aggressive or fast, but will strike if provoked. With this, we found descent walking sticks and set up the trail. 

The trail up Overlook Mountain is perfect for a moderately paced walk. As described by trail guides, much of the travel is a gravel or dirt road that gets occasionally rockier. It was used as an old jeep road by forest rangers to reach the cabin and fire tower at the top. While never very steep and easy to walk up, the kids enjoyed imagining what it would be like to drive our SUV up this road. After that, we talked about the history of the mountain. Talk of driving up entertained the kids and distracted us from noticing two springs that are present along the trail at 0.3 and 0.5 miles. At 0.9-mile, we came to the large rock that was Sara and the kids stopping point on the last trip. From there, I had gone to the top and met them on the return trip. Today, at Theo’s request, we all took a quick break at the rock, before continuing onward. 

The first mile of the trail is fairly straight. At about a mile, the trail turns to the right, and reaches a small fork at 1.2 miles. Stay left at this fork and continue towards the top. The trail gets a little rougher here and the incline becomes slightly steeper over the next quarter-mile, before becoming more moderate, and the ruins of the Overlook Mountain House appear. In some books and guides, it’s referred to as Catskill Mountain House. This really excited the kids and we talked about the history of the hotel. The original 300-room hotel burned in 1874 on April 1, when a chimney fire got out of control – after staff dismissed concerns of a child as an April fool’s joke, when they reported an unusual color of smoke coming from the chimney. After being rebuilt four years later, the hotel again burned down in 1924, and then struggled to stay open during the ensuing Great Depression. Efforts to rebuild the hotel never materialized. 

We were walking at a good clip so I promised if we went to the top first, we could explore more on the way down. Also notable in close proximity to the hotel ruins, is a large radio transmission antenna and a few smaller buildings. 

The remaining 0.5-mile walk to the summit went by quickly and we soon reached the old forest ranger cabin at the top. From the cabin, it is a short walk along the trail to the fire tower at the summit. It’s very important to pay attention to the signs and stay on the trail as you walk under the large scenic ledges on your way to the fire tower and ranger cabin. These ledges have timber rattlesnakes. Next to the fire tower is a grill and picnic table for anyone who wants to bring supplies up.

Even before climbing the fire tower it is not hard to understand why people have been writing about the view for over 200 years! The views from Overlook are truly spectacular in any direction. To the east, you can see the Hudson River and southeast brings the Ashokan Reservoir and Rhinecliff Bridge into sight. The view facing west includes Slide, Cornell and Wittenberg mountains, while north brings Indian Head, Twin, Sugarloaf, Plateau and Hunter into view. With so many of the Catskill 3500s in view, Overlook is a perfect easier hike to complete, which offers great exercise – and allows you to appreciate all that the Catskills have to offer! 

After enjoying the summit view, we made the short detour to the cliffs from the ranger cabin. These ledges likely give the mountain its name – Overlook. They offer additional unobstructed views of the Hudson Valley and Catskills. From here we made our way gradually down the mountain. As promised, we stopped at the hotel ruins. We enjoyed exploring but were careful to watch where we were going and I kept the kids nearby as the timber rattlesnakes have been known to make their way down to the hotel.

The kids enjoyed themselves so much on this trip that they asked if we could jog the remaining half-mile to the end. When we reached the bottom, I went to pick up the car, and picked everyone up at the main lot. By this time both lots were nearly full. On this trip, I covered six miles and everyone else approximately five miles. It took us a little over two-and-a-half hours to complete the round-trip, including a half an hour of exploring or enjoying the views. On the way home we stopped in the village of Catskill for dinner at a brewery and then got ice cream. This made for a fun day of exercise and exploring for Mother’s Day.

Tom O’Grady, PhD, MPH (thomas.james.ogrady@gmail.com) of Slingerlands is an avid runner, hiker and lover of the outdoors. He is an epidemiologist with NYS Dept. of Health. With a lifetime of racing experience, Tom has his NYS Dept. of Education coaching license, and is USA Track & Field Level 1 and Jack Daniels certified to coach distance runners and endurance athletes.