Go right at the traffic light and cautiously make your way down Route 9D for a quarter mile to the state-owned Castle Rock Unique Area. Take a left into the area, and head up the driveway, where you’ll enter the the Carriage Connector Trail. Follow the Carriage Connector Trail until the first marked turnoff, which will lead you on a bit of a scramble up the sharp rise of Sugarloaf Hill's east-facing rise. When you get to the top– roughly 800 feet above sea level—the valley lies at your feet. To the north, the river disappears behind the grey bulk of West Point. To the south lies the graceful arch of the Bear Mountain Bridge. Find a comfortable tree to rest against, and absorb the view.

From there, retrace your steps back to the Carriage Connector Trail's first intersection. A right-hand turn takes you onto the Osborn Loop. Heading south, follow the Osborn Loop’s blazes, which run roughly atop the spine of the hills, until you strike the Appalachian Trail. Its white blazes guide you through the serene high-country meadows of Canada Hill and South Mountain, and then leads you down the steep descent to South Mountain Pass, a narrow dirt road that hasn’t changed much in the last hundreds of years.

Pick up the trail, which takes the form of a broad carriage road, on the far side of South Mountain Pass. You'll be climbing again, and after about half a mile, you'll reach the Hemlock Springs campsite. From the Garrison Train Station, you've hiked about six miles. Depending on your energy and ambition, you can push on about one mile, and then bushwhack through some modest ground cover tenuously hanging onto the rugged scarp of Anthony's Nose, where you’ll discover views of Bear Mountain Bridge, Bear Mountain, and Dunderberg Mountain, which marks the southwest entrance to the Highlands.

Until a few years ago, working further south along the east bank of the river was impossible because Camp Smith, an Army Reserve site, was strictly off limits. Now, however, hikers can swing onto the Camp Smith Trail after a night at Hemlock Springs. The trail ends two miles north of the Peekskill Train Station at Routes 6 and 202. Follow the road into Annsville Circle, cross the creek (you'll see the train tracks on a berm crossing the broad mouth of the creek), and turn again toward the river at the first available spot. Kick back in Peekskill's waterfront park while you wait for a southbound train to pull into the station.

Move on to Dunderberg Mountain Return to Top