Overlook Mountain is positioned in Woodstock as the gateway to the nearly 1-million-acre Catskill Forest Preserve. While it falls short of the 3,500-foot Catskill High Peaks, its historical and spiritual significance give this 3,140-foot summit a special value to the local community.
Begin your ascent from the trailhead parking lot at the end of Meads Mountain Road. This is right across the street from the Tibetan Buddhist monastery of Karma Triyana Dharmachakra, which is open to visitors, and next to the infamous Magic Meadow of Woodstock Rainbow Tribe. Note that parking on the road here can result in a $150 fine.
The red trail will lead up the mountain at a fairly consistent grade on a wide road that passes through hemlock groves, northern hardwoods, and mountain laurel. Continue for 1.75 miles until you reach the remains of the Overlook Mountain House. Built in 1871, and again in 1878 after it burned, this was once the highest mountain house in the Catskills, and it could hold 300 guests. It burned a second time in 1924, and plans to rebuild it in 1928 crashed with stock market in 1929. The DEC currently advises the public not to enter these collapsing ruins.
Continue on the red trail past the radio towers and the blue trail intersection. In about a half-mile you will reach the summit and be greeted by a 60-foot fire tower that was constructed in 1950 and recognized by the National Historical Lookout Register in 1997. Climb to the top to see some of the highest peaks in the Catskills, and, on clear days, views that reach to six states. This is one of five remaining fire towers in the Catskill region. (The four others are Hunter, Tremper, Red Hill, and Balsam Lake.)
Do not leave without walking another tenth of a mile past the steward’s cabin (open in the summers) out to the more private Eagle Cliff, named by the landscape painter Charles Lanman, and also known as Minister’s Face. From here you can see to the Hudson River, Taconics, the Hudson Highlands, the Shawangunks, and the Ashokan Reservoir. You’ll notice names carved in the rocks that date back over 100 years.
Embrace this southeast limit of the Catskills that uniquely stands like a fortress wall against the backdrop of rounded mountaintops molded by glaciers 15,000 years ago. Local Native Americans once identified this place as a home to great spirits, and its location provides an excellent outdoor opportunity for young explorers as well as experienced adventurers.
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