March 15, 2025 – Woodstock, NY

Difficulty: Moderate – Strenuous

Length: Approximately 5 miles – total elevation gain approximately 1,400 ft.

Route type: Out and Back

Maps: Overlook Mountain Fire Tower Trail Map – Overlook Mountain Fire Tower Map for Avenza

Trailhead parking: 353 Meads Mountain Rd, Woodstock, NY 12498

Portable Toilets on site

Caution: Overlook Mountain has the highest population of Timber Rattlesnakes in the Catskill Mountains. They can be found anywhere from the parking lots to the summit of Overlook Mountain, and Echo Lake. The road to the summit of Overlook Mtn is very wide, so it is easy to avoid them. Please stay on the designated trails.

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Overview: 

Overlook Mountain is the southernmost peak of the Catskill Escarpment near Woodstock, NY. The centerpiece of the 590-acre Overlook Mountain Wild Forest area of Catskill Park, the mountain offers a unique combination: a historic fire tower, mountain house ruins, and impressive views of the Hudson River Valley and the central Catskills.

This is one of the busiest mountains in the Catskills. The summit of Overlook Mountain is one of the top three most visited locations in the Catskill Forest Preserve (after Slide Mountain and North-South Lake). On a typical weekend day in the warm weather, hundreds of hikers will make their way up and down the 2-½ mile gravel road that leads to the summit.

The Overlook Wild Forest is a small part of the Catskill Forest Preserve, but an extraordinary part of American history. The area has long influenced painters, writers and musicians, and played a prominent role in creating America’s perspective on nature and wilderness. It is owned and managed by the New York State Department of Environmental Conservation (NYSDEC).

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Parking:

The Overlook Mountain Trailhead, located on Meads Mountain Road, is the most visited trailhead in the southern Catskills. There is room for approximately 15-17 vehicles, depending on how well people park. The parking lot at this trailhead fills up quickly.

Overflow parking is available about a 1/2 mile down the road. The Meads Meadow Trailhead Parking Lot on McDaniel Road opened for public use in 2017. The overflow parking lot is located at 463 Macdaniel Rd, Bearsville, NY 12409 and can accomodate about 30 vehicles.

There is a 1/2-mile foot trail which connects both parking lots, eliminating the need to walk along the shoulder of the road. This connector trail ends near the kiosk, just past the gate of main parking area.

Please keep in mind that parking in the overflow lot will add 1 mile (1/2 mile each way) to the hike described here.

Parking is only available in the designated areas, please observe all posted traffic and parking signs, otherwise your vehicle may be ticketed and/or towed.

Restrooms:

There are portable toilets in the parking lot. 

There is also a Privy (outhouse) at the summit behind the Observer’s Cabin.

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History:

South Peak, as Overlook Mountain was once known, was described in detail by Charles Lanman in magazine articles and his book Letters of a Landscape Painter published in 1845. Lanman was a great admirer of the artist Thomas Cole (1801–1848) and for some time tried to persuade him to explore the mountain. Although Thomas Cole included the mountain in several of his paintings. It was not until 1846 that he visited, and played a part in replacing the name South Peak with Overlook Mountain. Thomas Cole, as far as is known, was the first person to set down in writing ‘Overlook Mountain’ as the name of the entire mountain.

Cole wrote of the view: “The vast valley of the Hudson lies like a Sea before and beneath you while the base of the mountain on which you stand rises abrupt and definitely from its misty bosom & seems like the prow of a stupendous vessel ploughing the great deep.”

Until the end of his life, Cole was drawn to the upper elevations of the Catskills. It was however, Overlook, to which he returned for a final visit. According to Cole’s biographer, Louis Noble, in The Course of Empire (1858), Cole was aware that he was approaching the end of his life when he chose to hike the Overlook Cliffs in October of 1847: “From this dizzy crag Cole took a long and silent look up and down the beloved valley of the Hudson. He had gazed upon it, from other points unnumbered times, alone and with companions. . . it had filled his heart for years. This was his last look.” Cole died a few months later at the age of 47.

Overlook Mountain House ~

The first of a long series of efforts to build a hotel on the mountain began in 1833; when Overlook Mountain was still known as South Peak or Woodstock Mountain. Nearby was Schue’s Pond, today Echo Lake. James Booth built a horseback – hiking trail that year to what he called a “temporary mountain house,” which he proposed to expand into a large structure, like the popular Catskill Mountain House. However, this venture did not survive the economic turmoil of 1833. Booth was followed by other disappointed Overlook dreamers – William Scobie, Nicholas Elmendorf, Robert Livingston Pell and Isaac N. Secor. Finally, a corporation with large stockholders, William Brinkerhoff (a Woodstock hotel owner) and Charles H. Krack (a summer homeowner who owned a floating bathhouse in New York City), succeeded. The first Overlook Mountain House was built in 1871 by designer and builder Lewis B. Wagonen of Kingston; but by then, the solitude, peace and beauty that had attracted the early visitors was in competition with the bluestone and charcoal industries. Tourism eventually prevailed. By the early 1900’s, Overlook Mountain was well known to the art community and nearby Woodstock’s reputation as an art colony was growing thanks to Ralph Radcliffe Whitehead’s arts and crafts colony Byrdcliffe.

The original Overlook Mountain House accommodated 300 guests by 1873. Destroyed by a chimney fire in 1875, it was rebuilt in 1878 by the Kiersted Brothers of Saugerties. In its early seasons, the Mountain House resembled a sanitarium for lung and tuberculosis patients especially since it was the highest elevation mountain house in the State. Anchored to the mountain by cables, the second mountain house stood three stories high and was 200 feet long. However, between the years 1887 and 1917 it operated irregularly. In 1917 it was sold to financier Morris Newgold, but was again destroyed by fire in 1924. Resurrected in concrete to become a grand hotel, it was never completed, a victim of changing public tastes and the automobile. Since 1940, when it was boarded up, theft, vandalism and the elements have brought it to its present condition.

Fire Tower ~

The Overlook Mountain Fire Tower is the newest of the five remaining fire towers in the Catskill Park, having been built in its present location in 1950. The tower closed in 1988 and was reopened in 1999, making it the first tower to re-open to the public in the Catskills. The steel tower offers incredible views of the Hudson River Valley across to the Berkshires, Taconics and Litchfield Hills, the Ashokan Reservoir and the Devil’s Path Range.

The Overlook Mountain Fire Tower is a standard 60′ Aermotor LS40 steel tower that was first erected on Gallis Hill in 1927. It was taken down by the Conservation Department and moved to this location in 1950. The tower has been restored as a part of the Catskill Fire Tower Project and appears in the National Historic Lookout Register. The tower sits at the 3,140′ ft. summit. The staircase is open every day at Overlook Mountain Fire Tower. The top cab is open on weekends and holidays from Memorial Day through Columbus Day when volunteer summit/fire tower stewards are present on the mountain.

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Trail Overview:

Starting at the Overlook Mountain parking area located on Meads Mountain Road, the red-blazed Overlook Spur Trail is a steady climb on an old carriage road that once transported guests in the late 19th century to the Overlook Mountain House and later, to access the fire tower.

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Hike Overview:

I rated this hike as Moderate – Strenuous, but that is subjective. The strenuous part is the first half of the hike that gains 1,400 feet of elevation. The moderate part is that it’s on a wide gravel road which is easier to walk than a footpath, and the second half of the hike is all down hill.

This is a pretty straightforward out-and-back hike on a wide gravel road. It’s almost impossible to get lost, even for the most navigationally challenged hiker. It’s a popular hiking spot so you will see other hikers, especially in warmer weather.  The hike described here is about 5 miles round trip.

As you can see from the elevation graph below, it’s a steep climb to the fire tower, approximately 1,400 feet of elevation gain.

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The Hike:

From the back of the parking lot on Meads Mountain Road, proceed past the gate onto the wide gravel road heading northeast on the red-blazed Overlook Spur Trail. The trail markers are scant, but the route is obvious. 

Please sign the Trail Register. Trailhead registers are used by the NYSDEC to estimate the amount of public use on State lands and as a guide to assist with management decisions regarding the use of public lands. Knowing how many people use the area determines the need for funding allocations. They also help SAR teams find you if you are lost, and provide a communication forum for hikers of current hazards or warnings.

The trail starts to climb immediately. This trail utilizes the existing gravel road which was constructed for access to the Overlook Mountain House and later, to access the fire tower.

After almost 2 miles of a steep uphill climb, the skeletal remains of the Overlook Mountain House come into view. You may want to take a little time to explore the massive concrete ruins. Please heed caution around the ruins for loose or falling concrete. There is a high population of Rattlesnakes in and around this area. Watch where you step.

Owned by New York City hotelier Morris Newgold, He began to make improvements, but the hotel burned down in 1924.

Newgold decided to rebuild, swearing to create a hotel that would “last the test of time and weather.” In 1927 he decided to build a four-story building out of concrete, including a power station and other amenities.

By 1935, he had spent $1 million, but Newgold died before it was complete. World War II was looming, and Newgold’s grandson was about to enlist. He had the grounds sealed up and joined the service. When he came back after the war, he found the building had been broken into and everything of value carted off.

Vandalized beyond repair, the hotel was abandoned for good. Ironically, now it’s more popular than ever, albeit not as an overnight stop.

The ruins are impressive and castle-like.

As you continue on the trail, you will encounter another smaller structure.

To the north of the main hotel is an old spring and reservoir, with nearby ruins of the “bowling alley.”

After passing the hotel ruins, continue to follow the trail uphill. From here it’s another 1/2 mile to the actual summit. Circling around a small cliff, hikers will reach the Observer’s Cabin.

There are several picnic tables at the summit.

A nice grill is available for use, but with the high winds probably not advisable. 

The 60-foot Aermotor steel tower with 7X7-foot metal cab was placed on the National Historic Lookout Register in October of 1997.

Originally built for Gallis Hill in Kingston, the tower was moved piece-by-piece to its present location in 1950. For outstanding views, you can climb the 81 steps to the top.

The high winds and cloud cover dissuaded me from climbing to just below the cab, which was locked. I went about half way, clicked some pics and descended.

View northwest from the middle of the fire tower.

Below is a similar shot on a clear day.

View southwest from the middle of the fire tower.

Below is a similar shot on a clear day with Ashokan Reservoir visible.

Overlook Mountain House ruins peeking out above the trees.

When you are done checking out the views from the fire tower, proceed past the Observer’s Cabin to the Scenic Overlook.

It’s a short walk on this footpath to a rock ledge with panoramic views to the east, south and west.

Not much to see on this day due to the low lying clouds.

Below is a similar shot on a clear day. The Hudson River is visible on the far left with Ashokan Reservoir on the right.

Below is a similar shot on a clear day. 

Here you’ll find graffiti carved into the rock going back to the early 1800’s. The one pictured below is 100 years old.

When you are done enjoying the views from the Scenic Overlook, retrace your steps past the Observer’s Cabin and proceed downhill on the Overlook Spur Trail.

You may want to stop at the Overlook Mountain House ruins again and snap some more pics before you make your way down the mountain.

From the ruins, it’s about 2 miles back to the parking lot, where the hike began.

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Review:

The hike itself is rather boring. A slog steeply uphill on an old gravel road with telephone poles and power lines overhead. However, the payoff makes it totally worth it. The massive ruins, views and the fire tower make for an enjoyable day on the mountain. This is a great hike for those that enjoy a good climb, but don’t care to venture into the deep woods. I have not seen any Rattlesnakes on my two visits to Overlook Mountain, but they are there. Both times that I have hiked Overlook Mountain took place in March so they were probably still in their dens. Awareness of high grass and rock crevices are essential to avoid any unwanted encounters with Rattlesnakes.

Pros:

Overlook Mountain House ruins, Overlook Mountain Fire Tower, Hudson Valley views.

Cons:

Old gravel road is monotonous, parking lot fills up quickly, tends to get crowded in warmer weather.

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Take a hike!

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Sources:

• Overlook Mountain Wild Forest
• National Historic Lookout Register
• Overlook Mountain – Scenic Hudson

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