Overlook Mountain Trail

The trailhead for Overlook Mountain is located on Meads Mountain Road in Woodstock. It is a large parking lot that holds about 30 cars, but it does fill up on a summer weekend. As you can imagine from the parking situation, this is a very popular trail! From the start, you'll hike on a graded gravel road, following red blazes, all the way to the top. After 1.8 miles, you'll see the ruins of the Overlook Mountain House. From here, it's just a short half mile to the fire tower on top of Overlook Mountain. After enjoying a quick view from the terra firma, climb the metal tower and see the great views from up top. On a clear day, you can see the Hudson River, Ashokan Reservoir, and the Catskill Mountains. Pro Tip: Pop on a pair of snowshoes and tackle this trail in the winter to have it practically all to yourself. While the spring, summer, and fall each bring a slightly different character to the views, the winter makes the surrounding area look utterly magical.