Fall is without a doubt the ideal season for hiking—the air is crisp enough to stave off sweatback, and the leaves do a neat thing with colors before they curl up and die, littering piles of crunchy leaf-corpses at your feet.
SUGARLOAF HILL/OSBORNE LOOP: One of the spectacular benefits of living in New York City is Metro-North, which makes a last-minute flee from the filthy pavement and crowds ineluctably easy to pass up. Take the Hudson line to Garrison, where you can enjoy the terrain around Sugarloaf Hill, which is part of the Hudson Highlands. Once off the train, a trailhead at the southern end of the parking lot takes you past some ruined brick buildings and over a wooden footbridge. The trail diverges at multiple points, but if you’re looking for a full-day hike, stick with the white-blazed Marcia’s Mile, which will eventually lead you up to the Garrison Institute. Set in a beautiful old monastery, several minutes spent on the Institute’s website have done little to help me understand its purpose. Still, its employees are incredibly friendly, and will offer you a basic map if you’ve forgotten yours, which you haven’t.
Once you leave the Institute, head toward the distant water tower and (carefully) across Route 9D. Enter Wing-Wing Road at the sign for Castle Rock Unique Area and tromp across the field until you reach another trailhead. From here, there are multiple routes available to you, demarcated by some combination of blue, yellow, red and white blazes. As ever, bring a good map and a compass, though the only real threat of getting lost is to follow the white blazes too far south, since white denotes the Appalachian Trail. The Osborne Loop, which adheres to some combination of blue and red blazes, is a mid-level hike that takes around five hours, affording occasionally spectacular views of the valley below and, toward the end, the imposing West Point military academy.
There’s not much by way of post-hike dining options available off the train, so take it one stop up to the adorable town of Cold Spring, where restaurants, bars and apothecaries abound. It’s an incontrovertible fact that beer never tastes as good as it does after a hike, so have two.