Overlook Mountain
Directions to trailhead
Take the New York State Thruway to Exit 19 and proceed west on N.Y. Route 28 for 5.9 miles. Turn right and head north on N.Y. Route 375 for 2.9 miles, then turn right onto Mill Hill Road. In 0.5 mile, turn right onto Rock City Road. In 0.6 mile, cross Glasco Turnpike and continue on Meads Mountain Road for 2.0 miles to the parking area at the trailhead. GPS address: 334 Meads Mountain Road, Woodstock, NY 12498.
Hike Description
From the parking area, follow the red-blazed Overlook Spur Trail that ascends Overlook Mountain on a gravel road. You’ll be climbing about 1,300 feet in elevation in the next 2.3 miles, with many views of the surrounding mountains as you climb.
About 1.9 miles from the start, you’ll come to the ruins of the former Overlook Mountain House on the right side of the trail. First built in 1833, it was rebuilt several times before being destroyed by fire in 1923. The owners started rebuilding it, but their efforts ended with the coming of the Depression. In the meantime, though, they had constructed a shell of concrete for the new building which, a century later, remains largely intact. These ruins are one of only a few extant examples of the Catskills' luxury destination status in the late 19th and early 20th centuries.
A short distance beyond, after passing a communications tower on the left, you’ll reach a junction with the blue-blazed Overlook Trail, which continues ahead. Turn right, and continue to follow the red-blazed Overlook Spur Trail.
In another 0.4 mile, you pass the caretaker’s cabin and reach the base of the Overlook Fire Tower. Climb the tower to take in the sweeping views of the Catskill Escarpment. The fire tower was originally built on Gallis Hill (west of Kingston), and was moved here in 1950. After extensive rehabilitation, it was reopened to the public in 1999. On weekends in the summer and early fall, a volunteer fire tower caretaker unlocks the cabin of the fire tower for even better views. For a bonus view, a short trail to the right beyond the caretaker’s cabin leads to a ledge overlooking the Ashokan Reservoir.
After taking in the spectacular views, retrace your steps, descending the mountain to the parking area.