Pound Ridge, New York

Looking for the best hiking in Pound Ridge? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pound Ridge. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Pound Ridge

  • Brooklyn, New York

    Brooklyn Bridge Walk via Brooklyn

    4.7
    1.12 mi / 0 ft gain
    Walking the Brooklyn Bridge from the Brooklyn side is a rewarding experience that blends history, architecture, and stunning views of New York City. Start your journey at the pedestrian entrance near Cadman Plaza, which is easily accessible by subway (Court Street or High Street stations). The br...
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  • West Milford, New Jersey

    Hike the Terrace Pond North - South Loop

    10.7 mi / 1200 ft gain
    From Warwick Road, parking at the northernmost road side parking area, cross the road, and the Terrace Pond North trail (marked with blue blazes) begins as a steady climb until you gain a ridge that offers some great views for several miles. Eventually, you'll reach a power line where you turn ri...
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  • Bloomingdale, New Jersey

    Norvin Green State Forest Loop

    5.0
    8.01 mi / 1538.26 ft gain
    Norvin Green State Forest is one of the best-kept secrets in the New Jersey Highlands — a rugged, rewarding stretch of the Ramapo Mountains that rewards hikers with rocky summits, cascading waterfalls, stream crossings, and sweeping ridge views. The 8-mile loop with 1,538 feet of elevation gain i...
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  • Brooklyn, New York

    Brooklyn Botanical Gardens

    5.0
    1.34 mi / 75 ft gain
    Brooklyn Botanical Gardens is a loop trail that takes you by a lake located near New York City, New York.
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  • Brooklyn, New York

    Prospect Park Loop

    4.7
    3.65 mi / 223 ft gain
    There are multiple places to enter Prospect Park. If you're looking for the main entrance to Prospect Park, it faces the stunning Soldiers' and Sailors' Arch in Grand Army Plaza. It is adjacent to the Brooklyn Botanical Garden, the flagship Brooklyn Public Library, and the Brooklyn Museum. As you...
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  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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  • Boonton Township, New Jersey

    Hike Pyramid Mountain to Tripod Rock

    4.0
    This is a fun hike that is great for the entire family. The trails are really well maintained and Tripod Rock is a pretty amazing feature to check out. You can hike to the rock and follow your steps back to the parking lot for a 3 mile round trip or continue along the trail for a 4.4 mile loop. I...
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  • 89 Van Orden Road, New Jersey

    Hike the Hank's Pond Loop

    7 mi / 500 ft gain
    Hank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road.  I hiked from the south on this trip.  Follow the wide trail known as Hank's East trail marked with white blazes.  Soon you will reach a trail c...
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  • New Paltz, New York

    Hike Mohonk Preserve's Gatehouse to Skytop Tower

    5.0
    9 mi / 1268 ft gain
    Begin at the intersection of Gatehouse Rd and Mohonk Private Rd. There is a small shoulder to park on here. Begin hiking into the preserve along the gatehouse road. There will be signs stating you need a membership or pass to enter. Don't worry about these, there will be a place on the trail ...
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  • Jefferson, New Jersey

    Thru Hike the Four Birds Trail

    19 mi / 1200 ft gain
    The Four Birds Trail is about 19 miles long and is a great thru hike or can be done in sections as out and back hikes or part of loop hikes with other trails.  Starting from the north, the trail ascends gradually over easy terrain until you reach a cliff ridge.  There are several good view points...
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  • Patchogue, New York

    Fire Island's Watch Hill

    4.0
    2 mi
    If departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...
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  • Vernon Township, New Jersey

    Stairway to Heaven

    4.8
    6.8 mi / 1089 ft gain
    This popular hike starts out on the Appalachian Trail (AT, white blazes). You begin on a boardwalk that crosses over a marsh, then you leave the boardwalk and enter a forested area. At around 1.4 miles, follow a bicycle path, Canal Road, then turn right, cross over a bridge, and take a left throu...
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  • Rockaway, New Jersey

    Hike the Timberbrook Pond - Riley's Rise Loop

    5 mi / 500 ft gain
    The trailhead parking is at the end of Timberbrook Road, before the road enters Camp Winnebago (Boy Scouts). I hiked this in a clockwise directions starting on the Timberbrook Trail (yellow markers).  After about 1 mile the trail ends at a junction with the Four Birds Trail (white markers).  Turn...
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  • 3197 U.S. 44, New York

    Hike to Sky Top via the Undercliff Road

    7.3 mi / 900 ft gain
    Starting from the East Trapps parking area ascend the East Trapps connector trail marked with yellow blazes.  You can also park at the Mohonk Preserve visitor center where you can purchase your access pass ($15 per person) and pick up a free map of the presere trails and carriage roads.  The conn...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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