The Overlook Mountain Trail isn’t all that long: just 2.3 miles to the top, then the same 2.3 miles back. It’s also not hard to get to; the trailhead is just a seven-minute drive from Woodstock, New York, the fabled little town that lies two hours north of New York City. On paper, this route might seem like any number of other trails in the Catskill Mountains.
Yet Overlook Mountain is in a class of its own. Standing 3,141 feet above sea level, Overlook earns its name, rising just above the rolling Appalachian Mountains all around. On a clear day, hikers at the summit can see miles of undulating forest. This is widely considered one of the most spectacular views in this upstate mountain range, and a rocky shelf at the top allows visitors to gaze across the horizon, a vista unobstructed by trees or fences. You can even see the Hudson River itself snaking its way between the rises.
Not high enough? There’s a fire tower that still perches on top of Overlook Mountain. First built in 1950, this 60-foot-tall structure is open to the public in all seasons; staircases lead to the top, broadening the panorama to 360 degrees. This alone would be worth the hike, but as it happens, the Overlook Mountain Trail offers a lot more than just an epic photo op. While this trail isn’t the most dangerous hike in the Catskills, it is definitely more strenuous than it looks on a map, challenging motivated hikers. Those 2.3 miles also pack in a lot of sights, including a Tibetan spiritual retreat and the surreal ruins of an erstwhile hotel.
Magical diversions on the Overlook Mountain Trail
The call of the Catskill Mountains
Upstate New York has a lot of well-trodden towns, but Woodstock is a household name around the world, thanks to the eponymous hippie music and art fair in 1969. The tiny community of 6,200 people is just a straight — and scenic — jaunt up the Hudson Valley from the Big Apple, so it’s a popular spot for New Yorkers escaping the city for some rural air. The county has more than its share of fun restaurants and art galleries, which make for nice pit stops on your way to the mountains. In all, the Catskills consist of 33 named peaks in the eastern part of the state; most are reasonable climbs for inexperienced hikers, with the tallest, Slide Mountain, rising 4,180 feet above sea level. The Overlook Mountain Trail connects to several longer trails, which extend, octopus-like, through the surrounding forests.
If you come with a tent, you’ll find a good number of established campgrounds in the area, including the charmingly named Sleepy Hollow Campground. Ulster County also has many hotels, but they’re quite a bit pricier than camping out, ranging from around $120 to nearly $300 per night. In general, the Hudson Valley makes for a great spot for a family getaway, especially in the fall.
If you’ve come to Woodstock for its countercultural history, there’s some bad news: The “Woodstock” festival actually took place in Bethel, about 90 minutes away by car. This drive actually cuts a beautiful cross-section of the Catskills, and you’ll be rewarded with the Bethel Woods Center for the Arts, which maintains the earthy creative traditions of the original events and regularly hosts outdoor concerts with big-name headliners.
