A weekend escape from the city doesn’t get any easier: Just take the train to the tiny town of Tuxedo and start walking. In 10 minutes, you’ll reach the trailhead for this 16-mile overnight loop, which skirts fish-filled lakes, open rock ledges, and a 15-foot waterfall. Take in views of New York City while keeping your eyes peeled for deer, wild turkey, threatened timber rattlesnake, and—if you’re lucky—a black bear.
From the Tuxedo station (1), head north to East Village Road; cross the train tracks and pass under I-87, then turn left onto Grove Drive. In .1 mile, turn right on the Ramapo-Dunderberg Trail into maple, birch, and hickory forest. At mile 1.3 (2), turn right on the Tuxedo-Mt. Ivy Trail and reach the Claudius Smith Den, an overhanging rock cave named for a Revolutionary War-era thief who hid out here. Brush the southern shore of Lake Sebago (3) at mile 3.3—no swimming allowed, but you can fish for bass.
In .4 mile, turn right onto the Hillburn-Torne-Sebago Trail (4), passing vast clumps of mountain laurel. Half a mile later, begin a steep, 400-foot climb over .3 mile to the rock-slab summit of 1,217-foot Diamond Mountain (5). Enjoy views of the lake below and rows of distant forested hills before descending on the Diamond Mountain-Tower Trail. After skirting Pine Meadow Lake on the Pine Meadow Trail, bear right on the Conklins Crossing Trail at mile 5.8 (6). Less than a mile later, turn right to detour .3 mile east on the Suffern-Bear Mountain Trail, past views of the sparkling Manhattan skyline from the aptly named Egg (a rock outcrop). Spend the night in or around the three-sided Stone Memorial shelter (7) at the edge of a burbling creek.
Next day, head south through flat, forested terrain for a mile, then make a right onto the Kakiat Trail (8). In 1.3 miles, turn right (9) to trek up a boulder field and onto the ledges of the Raccoon Brook Hill Trail for more vistas of nearly unbroken greenery before rejoining the Kakiat Trail at mile 10.5. The path soon parallels a creek, and in .5 mile, a 15-foot waterfall tumbles into a small, deep pool (10). In .4 mile, ford the usually shin-deep creek (11); the bridge was destroyed in 2011’s Hurricane Irene.
In 1.5 miles, turn right onto the Blue Disc Trail (12). Climb 260 feet in .2 mile to tag the 936-foot Almost Perpendicular viewpoint, then descend into sparse trees. At mile 14 (13), squeeze through a 1.5-foot-wide crack in the rocks. In .4 mile (14), turn left on the Tuxedo-Mt. Ivy Trail to close the loop.
Get there From Manhattan, take a New Jersey Transit train ($12 one-way; njtransit.com) or a Short Line bus ($14 one-way; shortlinebus.com) to the Tuxedo station. No overnight parking is allowed at the trailhead.
Gear up REI, 303 Lafayette St., New York, NY; (212) 680-1938; rei.com