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Oakland, New Jersey

Looking for the best chillin 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 Chillin Spots in and near Oakland

  • Staten Island, New York

    Sunrise and Sunset from the Staten Island Ferry

    5.0
    The Staten Island Ferry is a passenger ferry that runs between the boroughs of Manhattan and Staten Island. From the deck of the ferry, you will have a perfect view of The Statue of Liberty and Ellis Island. You'll see the skyscrapers and bridges of Lower Manhattan receding as you pull away and c...
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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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  • 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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  • Sandyston, New Jersey

    Hike the AT to Culvers Lookout Tower

    3.2 mi
    Start your journey in Stokes State Forest at the Culver Gap Parking Lot, located at 41.180239, -74.787954. From the parking lot, jump on over to the Appalachian Trail and hike Northbound. You know you're headed the right way if you are going away from the small town and cross over Sunrise Mountai...
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  • Washington Township, New Jersey

    Hike Hacklebarney State Park's Trout Brook Riverbanks

    5.0
    This is a relatively easy hike through Hacklebarney State Park that is great for families with younger children, rock scrambling, photography, and just hanging out in nature. There are two different ways to explore Hacklebarney, either by staying on the packed gravel path or by following the bank...
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  • Cold Spring, New York

    Photograph Indian Brook Falls

    2.8
    This is about as short a walk and as little effort as you can put in for a beautiful waterfall. You can barely call it a hike, but I'll list it as such since you do walk through the woods for 5 minutes. The trail is extremely well built, and is pretty easily accessible through the winter.The trai...
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  • Sandyston, New Jersey

    Explore the Sussex County Sunflower Maze

    5.0
    3 mi
    I stumbled upon the Sunflower Maze by accident when I was driving through NJ and was quickly distracted by the enormous yellow flowers. So of course, I had to check it out! It opens at 9AM and last admission is at 6PM. The maze is only open from around August to October for the flower bloom. 3...
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  • Dingmans Ferry, Pennsylvania

    Canoe and Camp in the Delaware Water Gap

    4.7
    This is one of those easy, simple and truly relaxing adventures you can embark on this summer. Thanks to outfitters such as Kittatinny Canoes you'll have everything ready for you when you arrive, minus of course your camping gear. They will pick you up at the destination of your choice along the ...
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  • Brooklyn, New York

    Camp at Floyd Bennett Field

    Brooklyn isn't just for the urban and trendy, its also for the people who love getting outside! Located just past the hustle and bustle of Brooklyn, Floyd Bennett Field is a National Recreation Area that features an Aviator Sports & Event Center (this was formerly an important NYC airport), t...
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  • Lehman township, Pennsylvania

    Hike to Hornbeck's Creek Waterfall

    4.3
    1.2 mi
    GPS Coordinates: 41.187148,-74.885454Driving Directions: From 209, enter into the Delaware Water Gap and in between the 10 and 11 mile markers you will see a sign for Hornbecks Creek with a gravel road adjacent to it. Follow the road back until you reach the parking lot and the trail will be to t...
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  • Califon, New Jersey

    Bike the Columbia Trail: Califon to High Bridge

    There are multiple places to pick up the Columbia Trail (High Bridge, Califon, Long Valley, Flanders) but this post is for biking or running from Califon to High Bridge and back. The best place to park is at the old town railroad station on, of course, Railroad Ave. You will be able to see the en...
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  • Beacon, New York

    Explore Long Dock and Dennings Point Parks

    4.0
    Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...
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  • 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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  • 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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  • 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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