Overlook Mountain

By Matthew Young
Overlook Mountain & Fire Tower
Woodstock, NY
5 miles roundtrip

“Never mind your replacement, the airplane.
You’ve pulled lightning from the sky,
tickled your legs blue with St. Elmo’s fire.
You’ve bathed in cold fog, shed icicles
like thousands of earrings. You’ve whistled
through hurricanes, watched meteors
scratch the black dome in every direction

without leaving a trace. You’ve ignored
wars. You couldn’t name a president.
You’ve chaperoned two generations of trees.
You’ve tolerated thousands of visitors
climbing the zig-zag of your spine
to stand inside your empty square head

& believe they see what gods see.”

-Will Nixon, volunteer fire tower steward

The Catskill Mountains have close to one hundred peaks with an elevation greater than 3,000 feet. Thirty-five of those peaks reach upwards past the 3,500 foot mark. The beauty of the region is undeniable, but as with much of New York State, there is more to the area than natural wonders. A history of Upstate New York wouldn’t be complete without the inclusion of the resort era. A time when grand hotels and resorts marked a surge of interest in the Catskill Mountains. Going back even earlier than the “Borscht Belt”, luxury hotels scattered throughout the region allowed guests to experience the solitude and peacefulness of New York’s Mountains.

Overlook Mountain, located just outside the town of Woodstock, combines some of the most inspiring views with an opportunity to travel back to a different time, and walk among the ruins of the now abandoned Overlook Mountain House. 


The trail parking lot is located on Meads Mountain Road, across from the Karma Triyana Dharmachakra Tibetan Buddhist Monastery. From the moment you park the car, and take a breath of the mountain air, there is a sense of well-being. On weekends, be sure to arrive early. The parking lot is relatively small and fills up quickly during the summer months. Besides finding a parking spot, early morning is a perfect time for finding some peace and quiet. The sunlight shines through the leaves, leaving a shadowed mosaic on the trail.

The trail begins as a wide dirt and gravel path and remains that way for the duration of the hike, well maintained and easy to follow. The forest on both sides is dense, allowing for partial shade. The climb to the summit is a steady 2.5 miles of uphill trekking. The shaded spots are perfect for a water break, or to cool off before continuing up the mountain. There is not a lot of landscape variation on the trail itself, but the end goal is worth the mileage.


Approximately two miles into the hike, one of the most unique aspects of Overlook Mountain comes into view. The ruins of the Overlook Mountain house, at first, are barely visible through the leaves. A staircase leading to the stone arch entrance is all that initially stands out from the foliage. The ruins are overgrown and a few trees have even taken root inside the shells of the former rooms.   


To provide some back story, this particular resort was not as fortunate or prosperous as some of the others during the same era. Fires, aided by the ebb and flow of the economy,  proved to be the downfall of three different resorts which stood at this same location. In 1871, the first Overlook Mountain house was constructed. With the ability to house 300 guest, it even attracted high profile vacationers, including President Ulysses S. Grant. Four years after its grand opening, the first Mountain House was reduced to nothing more than ashes after a fire devastated a majority of the property. Taking place on April 1st, the hotel workers originally thought the fire warnings were an elaborate prank, but consequently learned otherwise.

The second attempt at a mountain resort proved to be somewhat more successful. Built in 1877, the new hotel filled to capacity by the following summer, even hosting another presidential guest, Chester A. Arthur. It remained a lucrative business until the mid 1880’s, when the nations economy took a turn. After a lengthy slow period,  the resort once again started to see more visitors during the late 1910’s. However, as if the mountain was cursed, the second Overlook Mountain House also fell victim to the flames, and burnt to the ground in 1924. Believed to be the result of arson, the “Overlook Mountain Firebug” was never found.

The third and final Overlook Mountain house began its construction in 1927, with a second guest house built behind the main resort. This time it would be made with stone, rather than flammable wood. Though before the finishing touches were put on the project in 1939, the investor Morris Newgold passed away. The Mountain House was unused during WWII, and during that time period the hotel began its unfortunate descent into decay, leaving behind the walls and windows that still stand today. It had been looted and vandalized, and would never again open to the public. Fires once again broke out in the following decades, but the sturdy structure stood its ground, unlike its predecessors.


Walking through the ruins is like walking through a snapshot of earlier life in the Catskills. A life of luxury which had been masking the underlying hardships. You can drift through the Great Room, and down the stairs into what remains of the hotel’s lower levels. You can stare out into the quiet forest and imagine what life had been like for the guests of the long gone resort. The ruins can feel solemn and even sad at times, as they slowly collapse on the mountain top, but after years of being forgotten, there is a new sense of life in the area. Once again the Catskills are becoming a destination, not only for people living in New York City, but from all over. The history rich region is undergoing a revitalization, with new appreciation for its beauty, and storied past.

After some time spent wandering the Mountain House, continue on the trail which bends towards the right. If you are in the mood for a longer hike, the trail does split at this point, allowing you to continue straight towards Echo Lake and Devil’s Kitchen. However, the most rewarding part of the trail is less than half a mile from this junction. Follow the red trail markers to the right towards the Overlook Mountain fire tower, which can be seen further up the trail,  poking its head above the tree-line.


As you approach the summit, there is a small cabin which hosts a museum. Hanging on the walls inside are the skins of rattlesnakes, which are popular along the trail, as made clear by several “Rattlesnake Warning” signs. The museum also contains old photographs and a detailed history of the Overlook Mountain House, along with the location of the different fire towers spread throughout the Catskills. There were twenty-three original fire towers built, starting in 1909, after the area witnessed severe forest fires in the previous decades.


There is somewhat of a view from the rocky summit below the tower, but the best views are saved for the climb up the tower stairs. Because the stairs are relatively narrow, and since this specific fire tower is almost seventy years old, no more than six people are allowed up at the same time. The stairs can feel shaky at times, and the wind can be strong, but the tower remains sturdy. The 360 degree views that are visible even from the first platform are truly amazing. You can see a large stretch of the Hudson River as it flows towards New York City. You can see the high peaks that take on a blue color in the distance,  and the Ashokan reservoir, resting in the valley like a large lake. You can even make out the Shawangunk ridge in the distance.


The top of the fire tower is completely inclosed and serves as a windbreaker on especially windy days. Through the window panes you can see exactly what the lookouts would see, as the scanned they horizon for any signs of smoke, signaling a potential fire.

It’s silent at the top, level with the birds and glider planes that float their way down to the valley floor. As you make your way back down, each platform provides a slightly different view, every one just as beautiful as the last. Just a few minutes past the museum cabin is a second viewpoint, a small rocky outcropping with good views of the reservoir.


The views from this hike make it difficult to leave. With the thick forests that cover most of the Catskills, unobstructed 360 degree views are hard to come by. The Overlook Mountain hike is a true gem of Upstate New York. It can be easy to forget that places like this exist within a two hour drive of NYC. But still, these fire towers, coupled with the more recent charred remains along the Shanwangunk Ridge, are an example of how vulnerable the area can be. It needs to be respected in order to be enjoyed.


Walking back down the metal steps of the tower, I saw a single sentence someone had written on the handrail. A motto, placed as a reminder to those who might become overwhelmed with the commotion and anxieties of everyday life. It read “Hike more, worry less”. 

Stop by Hatchet Outdoor Supply Co. for detailed trail maps of the Catskills and beyond.

Also be sure to check out the Catskill Interpretive Center for brochures, guides, park information, and updated trail conditions!

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