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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

  • Califon, New Jersey

    Explore the Ken Lockwood Gorge

    4.3
    One of New Jerseys best kept secrets has to be the Ken Lockwood Gorge. If you are looking for a relaxing, beautiful, and nature packs place then this area is perfect for you. You can access the gorge from two different points, either by driving down Raritan River Rd. and parking right before you ...
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  • Beacon, New York

    Hike Fishkill Ridge

    Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...
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  • Beacon, New York

    Hudson Highlands Overlook Trail

    3.29 mi / 1017 ft gain
    Hudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.
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  • Pound Ridge, New York

    Leatherman's Loop

    1.25 mi / 1183 ft gain
    This loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...
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  • Kent, New York

    King's Chamber and Moose Hill Loop

    3.14 mi / 499 ft gain
    King's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.
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  • Bushkill, Pennsylvania

    Bushkill Falls Loop

    3.8
    1.89 mi / 331 ft gain
    Bushkill Falls offers visitors a choice of 4 different trails to explore. All trails are very well maintained, making this trip safe for the whole family. The most rewarding trail is the Red Trail. This route brings you to all 8 of Bushkill's waterfalls. Taking the trail counter-clockwise, you w...
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  • Matawan, New Jersey

    Cheesequake Yellow and Blue Loop Trail

    4.0
    3.43 mi / 328 ft gain
    Cheesequake Yellow and Blue Loop Trail is a loop trail that takes you by a lake located near Old Bridge, New Jersey.
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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  • Carmel Hamlet, New York

    Ninham Mountain Fire Tower

    5.0
    1.23 mi / 367 ft gain
    This is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...
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  • Columbia, New Jersey

    Hike the Mount Mohican-Raccoon Ridge Traverse

    7.5 mi / 1500 ft gain
    This point to point hike can be done in either direction. There is parking at the entrance to Worthington Campground. Cross Old Mine Road and start up the Garvey Spring Trail (orange markers). The trail passes Laurel Falls on the right then ascends steeply until you reach an old forest road.  The...
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  • Columbia, New Jersey

    Hike Mount Tammany's Red Dot and Blue Dot Loop

    4.5
    3.3 mi / 1197 ft gain
    Mount Tammany located in the Delaware Water Gap is a very exciting hike. Short in length but with steep, rocky uphill portions this becomes more of a challenging trek. This hike allows for amazing views of the Delaware River, Route 80, and Mount Minsi on the other side. The summit makes for an aw...
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  • Columbia, New Jersey

    Hike Mt. Tammany via Red Dot Trail

    4.6
    2.3 mi / 1115 ft gain
    This is a short but strenuous hike to a bluff overlooking the Delaware River and surrounding mountains and hills. The summit makes a good spot for a picnic or just for relaxing and watching the sunset. The entire hike also has plenty of beautiful photo ops, especially in the Fall. Find the trailh...
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  • Columbia, New Jersey

    Hike to Sunfish Pond

    4.5
    7.9 mi / 1150 ft gain
    At the end of the parking lot, cross over the bridge and follow the Appalachian Trail (AT, white blazes) to a V-intersection. Turn right onto Dunnfield Creek Trail (green blazes), which will take you past a few cascades and up to Sunfish Pond. Relax and eat lunch at the pond. When you're ready, t...
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  • Hardwick Township, New Jersey

    Sunfish Pond via Red Dot, Tammany Fire Road, Turquoise and Dunnfield Creek Trail

    5.0
    10.54 mi / 1434 ft gain
    Sunfish Pond via Red Dot, Tammany Fire Road, Turquoise and Dunnfield Creek Trail is a loop trail that takes you by a lake located near Pahaquarry, New Jersey.
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  • Cragsmoor, New York

    Sam's Point Overlook to Ice Cave Trail

    3.47 mi / 584 ft gain
    Sam's Point Overlook to Ice Cave Trail is an out-and-back trail with scenic views near Lake Maratanza located near Ellenville, New York. This trail is dog friendly on-leash. 
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  • Cragsmoor, New York

    Sam's Point, Ice Cave Trail, Verkeerderkill Falls

    4.9
    6.99 mi / 1063 ft gain
    Located in Sam's Point Preserve, this hike has three major attractions – panoramic views from Sam's Point, mysterious and chilly Ice Caves, and a knee-weakening perch atop Verkeerderkill Falls. Pay attention to seasonal conditions before making this trip. Spring and early summer are best for see...
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