Secluded trails winding through mixed forest. Fifty-mile views from rock domes. With charms like these—and the proximity to New York City—you’d expect to share every step, but this 18-mile overnighter sticks to the park’s quietest corner. From the parking lot (1) off Orange County Road 106, follow the red-blazed Ramapo-Dunderberg Trail on the ridge of Black Rock Mountain. Stay straight (2) and take in views of lakes shining like drops of mercury on a leafy background. At mile 1.8, turn left (north) onto blue-blazed Lichen Trail (3) and descend to the Long Path (4). At a four-way junction (5), head straight on the red-blazed Arden-Surebridge Trail for a short detour to the Lemon Squeezer (“See This,” next page).
Return to the junction and head north on the Long Path. Contour around Surebridge Mountain and past the shelter (6). Stay on the Long Path for a mile-long, low-country stretch in the shadow of 1,378-foot Fingerboard Mountain, then cross Arden Valley Road (7). Bear left (8) and climb steeply up 1,319-foot Stockbridge Mountain—its three-mile-long ridge reveals vistas of Bear Mountain (east), the Catskills (northwest), and West Point (north). After Hippo Rock, turn right onto yellow-blazed Menomine Trail and descend to Lake Nawahunta. Cross Seven Lakes Drive (9), skirt Silver Mine Lake, then ascend along Bockey Swamp Brook to the William Brien Memorial Shelter (10) in a hollow.
Next day, take the Red Cross Trail through a broad swath of lowland forest—one of the park’s least-visited areas. Stay right at the Y-intersection (11), and left to cross Tiorati Brook. Go straight in .6 mile, leaving the Red Cross Trail (12), toward Lake Askoti. Cross Seven Lakes Drive (13), and bend around Lake Skannatati on the Long Path. Turn left at the T-intersection, then left onto the Dunning Trail (yellow blazes). In .4 mile, continue straight to the Bald Rocks Shelter, then return via the Ramapo-Dunderberg Trail.
From Manhattan, take I-95 west to exit 74 onto the Palisades Pkwy. In 27 miles, take exit 14 and turn left onto CR 98. Take the second exit at the traffic circle onto Orange CR 106 west. Park in a mile.
Eastern Mountain Sports, 66 Rockland Plaza, NY 59, Nanuet, NY. (845) 623-5282; ems.com
New York-New Jersey Trail Conference Harriman-Bear Mountain Trails Maps ($10, nynjtc.org)