On Friday, October 20th I asked Cindy if she would like to go to Winter Clove and hike some of the trails there and she agreed. I checked my records and we had not been there in almost seven years! Winter Clove is primarily a resort which offers room and board and various activities to those who stay there. It is located north of Palenville with the address being Round Top. The drawback for us is that this is around a two hour drive but I did want to hike some of the trails which are really interesting. Winter Clove has miles of hiking trails open to those who are paying guests but they allow non-guests to hike which is very generous. The trails included several nice lookouts and waterfalls. There is even a trail to North Point and Stoppel Point although not all the trails are well-marked or well maintained. We got our gear together and prepared to leave the house. I had created a map for the Avenza app on my iPhone from some GPS tracks from previous visits. The temperature was cool but seemed to be rising so I put on a light jacket and took along a light hat and gloves. I decided to follow the route suggested by Google maps so at 9:10 AM we left Livingston Manor with an excited Sheila in the backseat. I drove through Liberty on Route 52 to Woodbourne and on To Ellenville. In Ellenville I picked up Route 209 north to Kingston. From there I took the Thruway north to Saugerties where I got on Route 32 north. I began to doubt my recollection of the route but found Hearts Conent Road just after the old Friar Tuck Inn. After a short drive, I made another left onto Winter Clove Road. From that point on there were small signs indicating the various resorts in this area and there are quite a few. We arrived at Winter Cove at about 11:10 AM. I got permission the night before so I didn’t bother to visit the office although I should have picked up some maps as many of their signs are keyed to their maps. I checked out some signs, set my GPS and we started our hike at 11:10 AM. The temperature was in the high 40’s when we started and it was getting warmer under sunny and cloudless skies. We followed the sign in the field just up from where we parked so we headed in that direction to begin our adventure. Just before we started out another hiker went out on the trails ahead of us. We saw him a few more times before we went our separate ways. He was the only person we would see all day!
The neatly lettered sign mentioned Indian Lookout and Rips Rock which were the destinations that held the most interest for us. We continued through the field down to a creek and across a small bridge. There were many maples in this area and each had at least one pipe connected to them for the collection of sap. The trail went through a series of switchbacks as it climbed a moderate hill with other trails branching off along the way. Some newer rails looked like single track mountain bike trails and we avoided these. There were some signs to indicate where we were going and red and blue paint blazes were also present. Soon the trail headed east and away from the brook through a field and passed by a small warming hut for skiers.We had been climbing some but not steeply and at about .6 miles a trail continued east toward “The Ledges”. I decided to save that for the return trip so we continued on the trail we were on, first west and then south. The trail were all very dry and I knew there was a forest fire alert posted. At one point we could see some elaborate stone work which lined the sides of a stream bed. At .9 miles another sign point to a spur trail to “Lost Pond” on the left but we stayed on the main trail. Around 1.2 miles another spur trail headed to “Lost Bridge” and just beyond that point was a short trail to the left to a campsite. Around this point we headed off the main trail to the west to check out the Webster Homestead. The family owned a large amount of farmland in the area and there was an interesting foundation not far off the main trail. After taking a few pictures we turned around and returned to the main trail. At 1.4 miles there was another sign pointing to The left to “Lost Pond” which made me think we might visit this attraction on the way back. At 1.6 miles we had the choice of turning left to the “Lower Rips Trail” or continuing on the trail we were on. We continued and walked parallel to a small brook that had cut a deep gorge between and into the surrounding rock. At 1.8 miles we cut across the streambed which had no water in it. I checked my GPS and the Avenza app and we were on the correct route to Rips Rock.
We had been gaining elevation from the time we left the Webster Homestead aging some 500 feet until the trail began to level a little and at 2.2 miles we arrived at Indian Lookout. This was an opening in the trees that looked out to the east toward the Hudson River. The view was nice and, as always near the Hudson, a little hazy. There was still some color on some of the trees. We stopped for pictures, a drink and a snack. It was clear that we were walking the edge of an escarpment but there was another, higher ridge of rock to our right. To this point the trail was clear and looked used. From this point on the leaves appeared undisturbed but I could the red paint blazes to mark the trail and I had the track on my Avenza app. We continued to follow the paint blazes from the Indian Lookout. The trail was level at first but then began to drop to a small streambed continuing to head south. The trail headed up a hill and we gained some more elevation. At 2.5 miles the a significant gorge began to appear and the trail swung left or southeast and ascended another small hill. I stopped to take a few pictures of the gorge. The trail hugged the edge of the top of the hill and then several views opened up of the opposite side of the hollow. There were interesting rock formations and the sun behind the ridge made for some interesting lighting effects. We stopped to take a few pictures since we had finally found some color in the leaves! We also had some limited views out to the Hudson River.
We slid down some slippery rocks and then ducked under and through some brush to find…a beautiful, expansive lookout toward the east and southeast. A small sign declared “Rips Rock 1,809 feet”. The deep chasm immediately to the south is formed by Stony Brook and is sometimes called Rip Van Winkle Hollow. The sun pretty high in the sky and I adjusted my camera to avoid it as I took numerous shots up the clove and out over the wide expanse of the valley below. Even the drop down into the hollow offered some nice photographic opportunities. Since we stopped, I took many pictures of the ridge, the hollow and to the east toward the river. Walking along the trail at the edge of the cliff was…exciting. The slippery leaves and overgrown brush tended to push us dangerously close to the edge but we made it in good shape. The views just kept getting better! We stopped two more times to take additional pictures before following the trail into the woods. The trail led us roughly around the top of the hill and we thought it might simply connect to the trail we used on the way up. It did not. After a trip around the summit the trail made a short steep descent between and over some rocks. The steepness and the slippery leaves made for an interesting descent. When I got down, I asked Cindy to pause for a minute and pose with Sheila. After this point, the trail changed character totally becoming wide and well-used. We continued to descend and hit a few switchbacks. The trail continued to parallel the one we took up but at a lower elevation. It became clear this was the “lower” trail from earlier and at 4.0 miles we were back at the junction. We turned right and began to retrace our steps back toward Winter Clove Inn. At 4.1 miles we came to the sign for “lost Pond” and decided we would take this trail as we knew it connected back to the main trail farther along.
At 4.6 miles I could see a large cleared area to the right of the trail which almost looked like a parking area. From the green cast of the ground I was convinced it was “Lost Pond. I took off my pack and got the camera to walk down and take a few pictures. As I started down to that area, Cindy yelled “Snake”! I cam back up to my pack and found a small snake coiled as if to strike. I took a few pictures and then used my hiking pole to challenge it. The snake did strike a few times and then slowly slithered off. I walked down to the cleared area to take a few pictures and the returned to my pack. We continued along the trail and at 4.9 miles we were back at the trail we had been on earlier. We turned right and followed the trail until 5.2 miles. At this point the main trail turned sharply left to head back to the car. We turned right to head toward the ledges. Within a short distance we came to a dirt road where we turned left. We walked along the road turning right at a fork and found “The Ledges”. From this open lookout there is a great view of what some call “The Great Wall of Manitou” which, in part, includes the Blackhead Range. I took some pictures and then we turned around and followed the dirt road back to our turn. From here we simply retraced our path along the trails back to the field and the parking area. We were back at the car at 3:05 PM having hiked 6.7 miles in 3 hours and 55 minutes gaining a total of 1235 feet.