Bear Mountain Bridge

Beginning at the southern entrance to the Highlands-Dunderberg Mountain, this ramble through Harriman State Park winds its way up and down through majestic rock outcroppings, stands of timber, uplands staples such as mountain laurel, and clumps of fern and bracken in the low, wetter spots. The trail also goes through one of the region's few utterly forgotten boomtowns: Just off the modern trail and easy to reach and explore, Doodletown was once a thriving little community. American troops on their march to triumph against the British at Stony Point followed these trails.

You'll note Doodletown’s status on your trail map is "abandoned," though evidence of its mines and quarries are still visible. The best way to incorporate a visit to Doodletown into this trip is to use two cars. However, if you have only one car, you can turn this hike into a full loop by linking the two trailheads with a 2.2-mile road walk on Route 9W.

Take the Palisades Interstate Parkway north to its end, and then head south on Route 9W once you hit the traffic circle just before the Bear Mountain Bridge. Prior to the entrance to the Iona Island Bird Sanctuary, you'll see a pull-off for the blue-blazed Cornell Trail. Leave one car here. Drive the second car an additional 2.2 miles past the sanctuary entrance to a turn-out just after the road reaches the high point on its climb up Dunderberg's eastern shoulder. Park here.

Across the road, marked by a rock cut, you'll see a red-on-white marker indicating the Ramapo-Dunderberg Trail. You'll also see a garbage recycling plant on the river's east bank, the Indian Point nuclear plant, and a set of transmission wires that swing in a long, ugly catenary across the river. But take heart, as it's the last you'll see of such ugly scenery.

You'll ascend quickly, crossing the grades of an ambitious–and failed–effort to build a scenic railway into the side of the mountain. Your course soon yields views of the valley opening up to the south. Continue on the Ramapo-Dunderberg Trail, which skirts a small pond as it works its way around to the north side of Dunderberg. Near here, a small outlook affords views upriver, revealing a glimpse of Mount Taurus and Mount Beacon on the east bank and Storm King on the west.

Pass the blue-blazed Cornell Trail on your right (north) and shortly thereafter, at an altitude of 1,100 feet, you'll come upon the deep pit of the Cornell Mine. One-fifth of a mile later, you'll find a southerly view topped off on a clear day by Manhattan Island in profile. If you're hungry by this point and the wind is blowing, hold out for the the better lunch spot up ahead. The trail now descends, crossing Timp Brook near its headwaters, then ascends to the top of the Timp to a stunning 360-degree view. Several sheltered spots provide good places to enjoy a wind-free break.

When you're ready to resume, continue along the Ramapo-Dunderberg Trail, which falls abruptly down the back side of the Timp. It's about 0.2 miles to Timp Pass, the intersection of three trails. Take a right onto unpaved Timp Pass Road—used for cross-country skiing as well—and follow it as it slopes gently down in a northeasterly direction for about 0.6 miles. At that point, it intersects the 1777 Trail, used by the British Army to approach and attack Forts Montgomery and Clinton. A left onto the trail, which at this point is following the remains of Pleasant Valley Road, puts you on the route to Doodletown. Almost immediately after crossing Timp Brook, you'll come upon a welcome shelter after a long day's work, located on the right side of the trail.

The second day's hike is shorter and flatter but no less interesting. Pick up where you left off on the 1777 Trail, and follow it into the eerie remnants of Doodletown. You'll see signs of what was, including the foundations of houses and two cemeteries. Today, Doodletown is best known as an outstanding place to spot northward migrating songbirds, particularly in May. You'll skirt Doodletown Lake and gently descend toward the Hudson. Watch for the intersection of the blue-blazed Cornell Trail, pick it up turning right, and you'll strike Routes 9W and 202 at the pull-off where you've left your second car.

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