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Woodbury, New York

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

Top Hiking Spots in and near Woodbury

  • High Falls, New York

    Mohonk Mountain House Labyrinth and Lemon Squeeze Hike

    4.5
    Mohonk Mountain House is a historic resort located just outside the Catskills in the Hudson Valley just 90 miles north of New York City. With 85 miles of winding trails throughout the Mohonk Preserve, you'll have endless hiking options upon your arrival.Parking at the Gatehouse is limited, so be ...
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  • Sussex, New Jersey

    Camp at High Point State Park

    4.0
    You'll need at least a weekend to sample all that High Point State Park has to offer. One of the park's must-do hikes is to High Point Monument (1,803 ft), where you have panoramic views of the Pocono and Catskill Mountains, and the Wallkill River Valley. Additionally, there are 50 total miles of...
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  • Yonkers, New York

    Run the Old Croton Aqueduct Trail

    5.0
    26.5 mi
    This trail traces the route of the Old Croton Aqueduct, which carried water to New York City between 1842 and 1955. Our recommended route starts near the Greystone Station in Yonkers, NY (Metro-North Hudson Line) and ends by the Scarborough Station, but you can easily modify your route – the enti...
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  • Wantage, New Jersey

    Hike the Iris Tail - Appalachian Tail Loop

    4.0
    9 mi / 1000 ft gain
    Start this hike from the Appalachian Trail parking area off route 23, south bound side, south of the park office. Follow the Blue Dot trail until is intersects with the Iris Trail. The Iris Trail (marked with red blazes) is a through hike that is about 5 miles long. It parallels the Appalachian T...
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  • High Falls, New York

    Scramble Bonticou Crag and Table Rocks

    4.5
    This is not a hike for the inexperienced. There is a very steep rock scramble that has some dangerous section if you are not aware of your footing and positioning. For those up to the challenge, it is extremely rewarding at the top.To start, each person has to pay $12 to access the Monhonk Preser...
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  • Closter, New Jersey

    Hike to Huyler's Landing/ Closter Dock Loop

    4.0
    5.4 mi / 450 ft gain
    The easiest way to access this loop hike is by parking at the Palisades State Park Headquarters.  This is just off exit 2 from the Palisades Interstate Parkway.  Parking here is free and it is a short walk down a road to the Closter Dock Trail.  The Closter Dock Trail is more of a wide fire road ...
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  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    7.5 mi / 1174 ft gain
    There are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road.  I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things.  For the most part the hike is flat but at some parts it c...
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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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  • 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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  • Frankford, New Jersey

    Picnic at the Sunrise Mountain Pavilion

    This pavilion is one of the key features along the New Jersey section of the Appalachian Trail. There is a parking lot a very short hike part way down the mountain, but I recommend backpacking in from a different area to take in more of the beauty of the trail, mountains, and views in this area. ...
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  • Danbury, Connecticut

    Hike Middle Mountain To Thomas Mountain Loop

    3.7 mi / 856 ft gain
    Middle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
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  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Huyler's Landing Loop

    9 mi / 980 ft gain
    There is two ways to access this loop hike.  The first is from the Englewood Picnic area just off Exit 1 from the Palisades Interstate Parkway.  Parking here requires a fee of $5 May through September. The second is to drive past the Englewood Picnic area turnoff on Henry Hudson Drive and continu...
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  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
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  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Carpenter's Grove Loop

    4.0
    4 mi / 400 ft gain
    This loop hike can be started from several different places.  I chose to start from Allison Park which overlooks the Hudson River in Englewood Cliffs, NJ.  From the parking area, walk out to the entrance road and travel south to Saint Peter's College.  The Long Path Trail, which you join from All...
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  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
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  • Cedar Grove, New Jersey

    Hike at Mills Reservation

    4.7
    2 mi / 200 ft gain
    Mills Reservation is over 150 acres of wooded area located off of Normal Ave. near the Cedar Grove reservoir. Parking space is limited due to the small size but there is another hidden lot towards the back if you make a right out of the parking lot and then the first right turn onto Highland Ave....
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