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DISTANCE: 4.6 miles TYPE: Out and back TOTAL ELEVATION GAIN: 1,380 feet MAXIMUM ELEVATION: 3,140 feet DIFFICULTY: Strenuous HIKING TIME: 3.5 hours |
Overlook Mountain is known less for the exciting nature of its trails than for the history waiting at its top. At the southeast edge of the range, just to the north of the town of Woodstock, the mountain played a major part in the Catskills’ status as a tourism destination for wealthy New Yorkers during the past century. While the route up is a plain yet grueling old carriage road making a steep, straight ascent, the rewards are worth it. The fire tower here is one of only five remaining in the Catskills (the others can be found on Hunter Mountain, Balsam Lake Mountain, Red Hill, and Tremper Mountain). Nearby, more history lurks in the woods: The former site of the Overlook Mountain House can be explored just off the trail.
The site of the former hotel is one of the few lasting reminders of the grand mountainside structures that once lured wealthy vacationers up into the mountains. The Overlook Mountain House opened in 1871, with a capacity for 300 guests and the highest elevation of any hotel in the area, at 2,920 feet. The business had several lives, as fire destroyed the structure in 1887 and again in 1923. Then-owner Morris Newgold hired architect Frank P. Amato to redesign and rebuild the hotel, but its final incarnation was ultimately never finished. The hotel’s elevation and lack of access to rail transportation made the site difficult to reach, and this ultimately thwarted plans for the hotel’s rebirth. Eventually, the project was abandoned due to financial difficulties, and the hotel was boarded up for good in 1940 after the land was acquired by the State of New York.
GETTING THERE
Take Exit 19 (Kingston) from the New York State Thruway. Keep right onto NY-28 West, then continue west on NY-28 for 6 miles. Turn right onto NY-375 North. After 3 miles, turn left onto Mill Hill Road, then continue through the town of Woodstock. From the center of Woodstock, take Rock City Road north. Rock City Road will turn into Meads Mountain Road after half a mile. Continue another 2 miles along winding mountain roads to the trailhead. The parking lot is large, but this is a very popular hike near a bustling tourist town, and the lot can easily fill up on weekends.
GPS SHORTCUT
Type “Overlook Mountain” into Google Maps and your GPS will navigate you to the appropriate trailhead.
THE TRAIL
The trail to the top of Overlook Mountain, following a well-graded gravel path, is incredibly easy to follow. In fact, this really isn’t a trail so much as an actual road, albeit a very grueling and unrelenting one.
At 1.25 miles in, you will encounter a branch where a side trail loops into private property. Stay left to continue on the main trail and walk for another half mile. Before reaching the top of the mountain, you will spot the ruins of the Overlook Mountain House in the woods. Be very careful when exploring the woods around the structures, as timber rattlesnakes are known to frequent this area. They are commonly seen around the road near the ruins and the summit both. The ruins themselves are, of course, very dilapidated.
Though the hotel has been out of use for almost a century, its past glory can still be felt over the sprawl of the complex. A large guesthouse still stands behind the Mountain House itself, with a stone pool that served as the water supply.
Continuing on from the ruins, 2 miles from the trailhead, you will encounter a trail junction. The path to the left continues northeast, toward Echo Lake and Platte Clove. To the right, the trail leads to the summit of Overlook Mountain and its fire tower.
OVERLOOK MOUNTAIN FIRE TOWER
THE RUINS OF OVERLOOK MOUNTAIN HOUSE
In less than half a mile, you will arrive at the ranger station and the peak of Overlook Mountain. The ranger station is staffed by volunteers most weekends from the end of May until October. There are picnic tables near the tower and ample spots perfect for a relaxing mountaintop picnic, but be wary of rattlesnakes here especially, as they are often found coiled up near the tables. Near the summit a short path extends to the east, leading to an excellent view of the southeast.
The 60-foot tower is the newest of those remaining in the Catskills. While the Overlook Mountain tower has only been at its present location since 1950, the tower was actually moved from its original location on Gallis Hill, near Kingston. It was built there in 1927. From the top, you will be able to enjoy breathtaking views of the Hudson River, Ashokan Reservoir, Indian Head Mountain Range, and West Kill Mountain.
Return along the same route back to the trailhead.
