Oakland, New Jersey

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

Top Hiking Spots in and near Oakland

  • 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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  • 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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  • 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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  • New York, New York

    Northwest Central Park Loop

    3.63 mi / 164 ft gain
    The Northwest Central Park Loop in New York City offers a scenic, family-friendly experience through some of the park’s quieter sections. The loop features well-maintained paths, stunning views of the surrounding nature, and landmarks like the Reservoir. It’s perfect for walking, jogging, or ca...
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  • New York, New York

    Jacqueline Kennedy Onassis Reservoir Running Path

    5.0
    1.68 mi / 69 ft gain
    Jacqueline Kennedy Onassis Reservoir Running Path is a loop trail that takes you by a lake located near New York City, New York.
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  • New York, New York

    High Line

    4.8
    1.47 mi / 26 ft gain
    Built on a historic freight rail line and perched above the streets of Manhattan’s West Side, the High Line is a public park that features a green-lined walkway. Park hours depend on the season, although it never opens before 7am, so best to go for sunset. Although you may have some company on wa...
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  • Pleasantville, New York

    Swan Lake Loop

    5.0
    1.37 mi / 85 ft gain
    Swan Lake Loop is a loop trail that takes you by a lake located near Hawthorne, New York.
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  • Briarcliff Manor, New York

    Hike Kate Kennard Trail

    1.8 mi / 140 ft gain
    If you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...
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  • Gillette, New Jersey

    Great Swamp National Wildlife Refuge Loop

    5.0
    0.94 mi / 43 ft gain
    Nestled within the more urban and suburban communities in Northern New Jersey, you can escape back to nature at Great Swamp National Wildlife Refuge. The name says it all - this place is the perfect opportunity to get up close to a variety of different wildlife that call this protected land home....
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  • Monroe, New York

    Hike the Jessup/Highlands/Long Path Trails

    7.8 mi / 500 ft gain
    This trails starts at a small park in Woodbury called Gonzaga Park.  Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking.  Three different trail names share this path.  The Jessup trail starts/end at Gonzaga Park and trave...
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  • New York, New York

    Brooklyn Bridge Walk

    5.0
    2.4 mi / 26 ft gain
    Brooklyn Bridge Walk is an out-and-back trail that takes you by a river located near New York City, New York.
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  • Bear Mountain, New York

    Hike Bald Mountain, Bear Mountain State Park

    4.7
    6.8 mi / 1080 ft gain
    From your starting point at the Bear Mountain Inn, go left along the Cornell Mine Trail. (This part can be a bit confusing, but go past the carousel to a shaded picnic area; that is where the trail starts.) You will go under a bridge and follow the trail until it takes a sharp left and descends t...
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  • Highland Falls, New York

    Popolopen Torne

    4.5
    1.18 mi / 531 ft gain
    Popolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...
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  • Cortlandt, New York

    Camp Smith Trail

    4.0
    5.92 mi / 1759 ft gain
    This approximately 3-hour hike borders the Hudson River, and is one of the best in Westchester County. Start off at the parking area at the Bear Mountain Tollhouse, or at a small parking area farther up Bear Mountain Road, if you want a slightly shorter hike. The trail is fairly steep in places, ...
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  • 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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  • Philipstown, New York

    Anthony's Nose via Appalachian Trail

    4.6
    1.95 mi / 682 ft gain
    Parking for the trail runs along both sides of 9D right up until the Bear Mountain Bridge. It can be busy on the weekends so just make sure you're as far off the road as you can and be especially careful unloading kids and dogs. The trailhead is located at approximately 41.322571, -73.975949 and ...
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