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Hudson Valley, NY, Hiking Trails and Paths with the Best Unusual Terrain


Undercliff/Overcliff Carriage Roads, Mohonk Preserve

Length: 4.7 miles • Elevation: Approximately 900-1,000 feet • Highlight: Watch rock climbers dangle in the air

Beginners and less-experienced hikers will love this trail, which offers terrific scenery with only a moderate amount of sweat. Something of an engineering marvel when they were built (by hand) on solid rock in 1903, these two carriage roads circle under and around the precipitous cliffs known as the West Trapps — the most popular rock-climbing area in the Shawangunks (which in itself is the most popular rock-climbing destination in the entire U.S.). As the name implies, Undercliff skirts the bottom of the cliffs, which rise as much as 300 feet above the road. Climbers can often be seen clinging to the dramatic rock face, which features huge boulders that jut out at seemingly impossible angles above your head. Follow Undercliff to Rhododendron Bridge, a multi-trail junction, where it meets up with Overcliff Road. Overcliff takes you around to the opposite side of the ridge, where (depending on the season) you’ll see mountain laurel in bloom and wild blueberries ripe for the picking. And the views to the north and west — of the Rondout Valley and the far-off Catskills — are none too shabby either. You’ll come to appreciate why the Nature Conservancy named the Shawangunk Ridge one of its “last great places on Earth.”


Albany Pine Bush Preserve One of the world’s largest inland pine barrens, this 3,000-acre preserve is home to pitch pine and scrub oak trees, as well as the Karner Blue Butterfly (an endangered species).

Sam’s Point Preserve This preserve near Ellenville features ice caves formed more than a half billion years ago. Rare vegetation, along with shimmering ice and snow, can be seen throughout the year.

Lemon Squeeze/Lemon Squeezer There are two claustrophobia-inducing rock crevices with similar names in the region: Located at the grounds of the Mohonk Mountain House, the Lemon Squeeze is found along the .4-mile Labyrinth Trail near Skytop Tower. Harriman State Park is home to the Lemon Squeezer, another narrow, rocky route that’s part of the Appalachian Trail.

» Back to the Hudson Valley’s Best Hiking Trails 2011

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