A Popular Catskill Mountains Trail Offers Unmatched Views Of New York's Hudson Valley

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.

Before you even set foot in the forest, you'll spot the colorful grounds of the Karma Triyana Dharmachakra monastery. Like a little slice of the Dalai Lama's home turf, this temple is built in the traditional Buddhist-Himalayan style and contains eight different stupas, which chronicle the life of Siddhartha Gautama, the mystic founder of Buddhism. The building is open to the public 6 a.m. to 9 p.m., and it makes for an illuminating stop before or after an alpine trek. You'll be welcomed by monks in robes and can place a lamp on the temple's main shrine as an offering.

The trailhead has a modest parking lot, and the trail is open year-round and free to hike. As you approach the top, you'll come upon the Overlook Mountain House, a sizable hotel built — though never completed — in the 1920s. Several hotels have occupied this property starting in the 1800s, each with its own tragic end, and this deco-style version never had the chance to welcome a single guest. What remain are several high concrete walls, with empty doors and windows and vegetation growing through cracks and openings. The old stairway looks like it leads into some kind of ancient fortress, though it should have become a flapper-era resort with mountain views. A previous incarnation of the hotel was destroyed by a fire, and you wouldn't be the first to think the place is haunted.

This trail is best suited to fit hikers with at least some experience; plan to budget about three hours to reach the top and return to the trail head. There aren't any fresh water sources as you ascend, so make sure to bring plenty of provisions. Not much practice in this area? Here are some food and drinks hacks to better prepare you for a hike.

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.