By Clifford Hart (Recycled from May 2014, Edition 6)
Photos: © Greg Miller Photography
I had often admired Overlook Mountain located in Woodstock from afar, as a kid in the backseat of a ski-laden car hurtling up the New York State Thruway. Because of its great height relative to its immediate surroundings, I always imagined Overlook would be quite a challenge to climb. So one early-spring morning a few years back, after poking around some old trail guides that had lots of pictures but not much information, I decided to give it a whirl.
As I headed north out of Woodstock on Meads Mountain Road, my first surprise was how far up the mountain I was able to climb without setting foot out of my car. Arriving at the well-maintained parking area across from a monastery, everything looked so peaceful and inviting I wondered if I might be in the wrong place.
You see, I’d had some experience with early-spring day hikes gone awry. All too often I’d thrown an apple and a water bottle in my bag and headed up a welcoming trail, only to find my way stymied by icy winds and muddy ravines from all the snowmelt running down the mountainside. So this time I made sure I was prepared, stuffing extra layers of outerwear, shoes and socks into my daypack.
I might not have bothered. Within a few short minutes, I found myself sauntering up a wide trail that was more like a fire road, appreciating the steady grade and easy footing on the dirt-and-gravel surface. It was not to last, however, as the fire trail shrunk to become more like other mountain trails I’d hiked in the Catskills. By that point, I’d climbed high enough where patches of snow were visible in the surrounding woods, but the trail continued to be dry, and I was able to make good time.
After perhaps 10 minutes more, I was perched atop the high fire tower, startled not only by the view—a gorgeous panorama of the Catskills and the great Ashokan Reservoir to the south—but also by the fact that I’d done it all in early April and had needed only one pair of light hiking boots, a fleece and a windbreaker.
This isn’t to suggest that mountain weather isn’t always changeable; it’s always wise to be prepared with extra gear—just in case. But having now climbed Overlook in every season and in every kind of weather, I have to say that it’s never failed to delight for its wonderful combination of beauty, views and relative accessibility. █