Overlook Mountain, located just outside of the Ulster County town of Woodstock, is a magnet for hikers of all ages, abilities, and interests. The five-mile round-trip hike begins on the Meads Road trailhead and follows a trail up 1,400 feet to the summit, where ruins and a fire tower with spectacular views await.
Above: The view from Overlook Mountain.
The much-loved hike is an attraction for families, photographers, birders and dog owners. (Because you may get a rare glimpse of a timber rattlesnake, it's a good idea to keep your dog on a leash.)
On any morning of the week, locals use the Overlook trail in place of a morning visit to the gym. Weekenders, people on vacation and anyone else out to enjoy the cool ambience of Woodstock may find themselves hiking to enjoy the gorgeous summit views.
Besides the 360-degree view from the restored fire tower on the summit, there is a short path leading to the overlook for which the mountain was named. On a clear day, the views from the open cliff top can encompass views that include southern Vermont, Massachusetts, Connecticut, the Shawangunks and the lower Hudson Valley, where you can also see miles of the Hudson River.
Above: The alidade map in the cab in the Overlook Mountain Fire Tower.
Look for a number of places along the trail where the rare American chestnut tree is found growing right alongside the path. A blight wiped out was once the predominant tree in the eastern U.S. forests, so seeing a chestnut in the wild is an event. Mountain laurel also line the path, and in the spring they bloom with fragrant pink-and-white blossoms.
The trail passes the eerie stone walls of an old hotel located a short distance before the summit. Generations of hikers have left graffiti here, and it's a popular place to pose for photographs.
Above: The remains of a hotel on Overlook Mountain.
If you're fortunate you might get a chance to see one of most famous locals. Overlook is home to crotalus horridus, or the timber rattlesnake. These shy, slow-moving reptiles are sometimes seen along the trail, but more often they can be found on open summit ledges when the temperatures are to their liking. Most summit visitors aren't fortunate enough to see one, but it's a treat for the hikers who get to experience one of these uncommon, protected reptiles.
Above: A sign warning hikers about timber rattlesnakes on Overlook Mountain.
Alan Via is the author of “The Catskill 67: A Hiker’s Guide To The Catskill 100 Highest Peaks Under 3,500” and many articles on the Adirondack and Catskill Mountains. He is working on two new hiking guides. He is also one of the tower volunteers at the Overlook Mountain Fire Tower, and on Saturday, Aug. 8, he will be at the top of the fire tower to greet visitors. Come by and say hello.