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

  • 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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  • Warren County, New Jersey

    Mt. Tammany via Red Dot Trail

    4.6
    2.59 mi / 1167.98 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 trail...
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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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  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    5.0
    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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  • Bangor, Pennsylvania

    Hike Mount Minsi

    3.6
    This is a great 5.5 mile hike at the Delaware Water Gap. You follow the Appalachian Trail the entire time (white marked trail) as it climbs to the top on Mt Minsi. There are multiple viewpoints on your way up that provide a great view of the water gap as well as some very picturesque trail points...
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  • Washington, New Jersey

    Merrill Creek Reservoir Perimeter Trail

    4.0
    5.33 mi / 371 ft gain
    Merrill Creek Reservoir Perimeter Trail is a loop trail that takes you by a lake located near Stewartsville, New Jersey.
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  • Barryville, New York

    Camp at Kittatinny Campground

    This campground is perfect for a group of friends that want to spend a couple days outdoors camping!With 350 campsites, there are many different types of sites available: from sites with electricity to sites 3 miles from the main camp. Decide how intense (or not intense) you and your group want ...
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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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  • Hopewell, New Jersey

    Hike through the Sourland Mountain Preserve

    5.0
    2.91 mi
    The Sourland Mountain Preserve stretches from Hunterdon County all the way into Somerset County. The trails referenced here are on the southwest side of the preserve in Hunterdon County. They are accessible from an on site parking lot at 233 Rileyville Road in Ringoes NJ.There are several trails ...
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  • Gardiner, New York

    Millbrook Mountain & Gertrude Nose loop

    8.77 mi / 1253 ft gain
    This great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...
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  • Gardiner, New York

    Lake Minnewaska Loop Trail

    2.01 mi / 348 ft gain
    Lake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.
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  • Gardiner, New York

    Gertrude's Nose

    4.9
    6.97 mi / 919 ft gain
    It would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...
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