Often cited as the toughest hiking trail in the East, this east-to-west voyage in the Catskill Mountains of New York traverses the spine of the mountain range. It is just two hours north of Manhattan, but the route is wild; hikers will find rocky and near-vertical sections, waterfalls, and slippery slabs of rock on knee-crushing downhills. Long, precipitous, and difficult, the path travels 25 miles and ascends six major Catskill peaks. And did we mention the bears? Be sure and hang your food supply in a tree at night to avoid black bear harassment.