Overlook Mountain. Looming over Woodstock, the 3,140-foot Overlook Mountain offers one of the best views in the Catskills—on clear days you can actually see five neighboring states. On the way up the demanding 2½-mile gravel road—it's an almost constant ascent—you'll see the ruins of the Overlook Mountain House, a once grand hotel. The old fire tower at the top is a favorite destination for hikers. The trailhead and parking are across the road from Karma Triyana Dharmachakra Monastery. Off Meads Mountain Rd., Woodstock, New York. 845/256–3000; www.dec.ny.gov/lands/73982.html.