A Hike Up Overlook Mountain-Catskills, NY

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New York is full of stunning and enjoyable hikes. There are hikes for all skill levels and physical shape. Catskill, NY is full of great hikes and is still a popular vacation destination. Overlook Mountain, which elevates 3,140 feet above Woodstock, NY, is one that offers stunning views, but also has a little extra to offer.

On a crisp, fall morning we set out for our 4.6 mile round trip hike up Overlook Mountain. Overlook Mountain had an additional appeal for us as urban explorers. Just before the summit sits the Overlook Mountain House, or rather the remnants of what was once the Overlook Mountain House.

We ran into out first problem upon arrival. The parking for Overlook Mountain is limited and fills up very quickly in the morning. We set out early in the morning, arriving at approximately 9am. By this time the parking lot was already overflowing, but we were able to squeeze into a spot close to the road. WARNING: If you are going to hike Overlook Mountain take the no parking signs along the roads very seriously. The roads lining the entrance to Overlook Mountain are full of them and police do patrol the area quite frankly. If you are parked in a non-parking area you will receive a parking ticket and may be towed.

There is additional parking for Overlook Mountain about a half mile down on Macdaniel Road. This parking holds room for approximately 30 cars. There is a trail that connects this parking lot to the main trailhead. This parking option will add approximately another mile on to your hike round trip, but it is a relatively easy mile.

We set out on what we thought was going to be an easy flat hike. We soon realized that this was not going to be the case. The trail is the remnants of an old gravel road that was once used as a carriage road to bring guests to the Overlook Mountain House. The path, therefore, may be a little easier to navigate than a traditional hike through the woods. The thing that makes the Overlook Mountain trail a little more difficult is the fact that it is uphill nearly the entire distance. You do occasionally get a break with some level ground, but these are few and far between.

One thing to point out is there were plenty of large rocks along the trail, great places to sit and take a break. There is not too much to be said about the actual trail itself because, as I stated before, it is an old gravel road that is a relatively straight forward hike.

After about a mile and a half of hiking we saw the ruins of the Overlook Mountain House is the distance. This was very rewarding and quite honestly relieving. I was beginning to feel like we would never get there! You will first come upon a stair case leading to a stone circular piece that I assume was once a garden or fountain. Continue on past that and you will come to the main entrance of the hotel. All that remains is the outer concrete walls of the hotel, the interior had been destroyed in a series of fires. You can find more on the history of the Overlook Mountain House here.

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After entering the main entrance, you will come upon a staircase going to nowhere (must have once led to the second floor) and a large fire place. There are a couple wall remnants of rooms that once stood within the glorious hotel. To the right of the entrance is a staircase that goes down to a lower level of the hotel. To the left there is another small room and an exit door. If you follow through that door you will come upon the remnants of the lodge. This lodge was once home of the owners of the hotel.

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After spending some time exploring the ruins and taking a short break, begin the final ascent up the mountain. After a short hike you will come upon the signs that warn of rattlesnakes in the area. This is the beginning on the summit. Be very cautious at this point, paying attention to where you step. If you are cautious you should not have any problems, but the last thing you want is to step on a rattlesnake. On our visit we did not see any, but it was a chilly day. Many people have reported coming into contact with them.  

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Continue on and you will come to a ranger station with a cabin. There is usually someone sitting at the ranger station providing you with encouragement and a little history of Overlook Mountain. They may also give you a couple safety tips. Take a look inside the cabin and check out some of the history of Overlook Mountain and the Overlook Mountain House. After this continue on to the summit and fire tower. Climb to the top of the fire tower and you will be provided with some stunning, 360-degree views of the Catskill Mountains. After climbing down grab a seat at one of the many picnic tables and enjoy some lunch (if you packed it) while relaxing. When ready, continue on behind the cabin on the short, rocky path. This will take you to the cliffs of Overlook Mountain, which provide some more great views of the mountains. After this, you have fully explored Overlook Mountain and may begin your descent.

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After descending the mountain (or before) feel free to visit the Buddhist temple that sits directly across the street from the trailhead. We were unable to due to time constraints, but I know of many people that have and they state it is beautiful. It is commonly visited and there is a gift shop, so don’t feel out of place if you do decide to check it out.

Simple Trail Directions:

1. Park at the trailhead or additional parking and head to the main trailhead.
2. Sign in at the kiosk and begin hiking up the road. It is very visible and not easily missed.
3. Continue walking up the road. After about 1.6 miles you will come upon the remnants of the Overlook Mountain House. Spend some time exploring the remains, but be very safety cautious. Hikers are permitted to enter the ruins, but be aware that you are entering at your own risk. (P.S. we did not see any obvious dangers while exploring them).
4. After exploring the remnants of the Overlook Mountain House, continue on the path. You will come to a fork in the path with signs clearly directing you to the summit.
5. Continue on and you will soon begin to see signs warning you of the rattlesnake habitat you are entering. Take note of this and be cautious. Watch your step. We did not see any rattlesnakes on our visit (it was a chilly day) but many people report seeing them. The last thing you want is to step on one.
6. Continue walking around the curve and you will come upon a ranger station and some outhouses. There is usually someone at the rangers station providing information and a quick snack.
7. Take some time walking through the cabin with information on the history of Overlook Mountain.
8. After this head over to the fire tower. Climb to the top and you will be greeted by stunning 360 views of the Catskill Mountains. Near the fire tower are several picnic tables. If you brought lunch this is a great place to sit and enjoy it.
9. After exploring the fire tower head back behind the cabin. There is a short, rocky path that leads down to the cliffs of Overlook Mountain. You again will be greeted with some beautiful views of the Catskill Mountains.
10. After fully exploring the summit, fire tower, and cliffs begin your descent back down Overlook Mountain.

In its entirety the hike took approximately three hours, and we were going at a somewhat slower rate. We were traveling with a beginning hiker and had to make many stops.

Overlook Mountain is a family friendly hike, but I would not recommend taking young children who may have trouble making it up the steep path. Older children (at least 6 years), however, should have no problem if you go at their pace, and they will love exploring the ruins!

You can find more images of the Overlook Mountain House here.

Published by Melissa

Hello! My name is Melissa (or Missy). I'm a nurse by day, but my true passion is travel. I'm a part time traveler, travel blogger, and photographer. Travel blogging allows me to share my experiences and knowledge with you as well as allows me to share in your experiences and learn from you. View all posts by Melissa