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Staatsburg, New York

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

Top Hiking Spots in and near Staatsburg

  • Washington, Connecticut

    Hike Meeker Trail

    3.3 mi / 639 ft gain
    Meeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.
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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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  • Windham, New York

    Backpack the Catskill's Escarpment Trail

    32.4 mi / 8000 ft gain
    The Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Philipstown, New York

    Hike the Osborn Loop

    7.6 mi / 850 ft gain
    The Osborn Loop trail itself is not a loop.  It connects to a 2.5 mile section of the Appalachian Trail.  Hiking these together creates the loop.  Start at the trail head for the Appalachian Trail on South Mountain Pass Road.  There is parking for two or three cars.  Walk up the road a short dist...
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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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  • 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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  • 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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  • 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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  • Cortlandt, New York

    Hike the Camp Smith Trail

    4.5
    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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  • Norfolk, Connecticut

    Hike to Campbell Falls

    4.0
    1.4 mi / 187 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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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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  • 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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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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