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Rye, New York

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

Top Hiking Spots in and near Rye

  • West Milford, New Jersey

    Hike the Terrace Pond North - South Loop

    10.7 mi / 1200 ft gain
    From Warwick Road, parking at the northernmost road side parking area, cross the road, and the Terrace Pond North trail (marked with blue blazes) begins as a steady climb until you gain a ridge that offers some great views for several miles. Eventually, you'll reach a power line where you turn ri...
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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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  • Beacon, New York

    Mt. Beacon Fire Tower

    4.8
    3.83 mi / 1332 ft gain
    Mount Beacon is a very popular trail along the Hudson River, and for good reason. It offers a good workout, fantastic views for both sunrise and sunset (and of course the time in between), a recently rebuilt fire tower, and all with incredibly easy access right on the edge of a lively town. The ...
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  • Beacon, New York

    Malouf's Mountain Camp on Mt. Beacon

    7.02 mi / 2087 ft gain
    Starting in the quaint town of Beacon there are a couple of options for hikes of varying difficulty. From the station the walk is about 1.5 miles to the trail heads, alternatively if you choose to stay the night at Malouf's Mountain Sunset Campground you can arrange for the host to meet you, take...
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  • Beacon, New York

    Hike the Scofield Ridge Loop

    7.5 mi / 1850 ft gain
    There are some great view points along this route.  Start from the Mount Beacon Park trailhead parking area.  This leads to the Casino Trail (red markers).  The trail climbs steeply to some old ruins of a casino.  Most of what remains is only the brick structure housing the mechanics for a trolle...
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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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  • 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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  • Jefferson, New Jersey

    Thru Hike the Four Birds Trail

    19 mi / 1200 ft gain
    The Four Birds Trail is about 19 miles long and is a great thru hike or can be done in sections as out and back hikes or part of loop hikes with other trails.  Starting from the north, the trail ascends gradually over easy terrain until you reach a cliff ridge.  There are several good view points...
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  • 89 Van Orden Road, New Jersey

    Hike the Hank's Pond Loop

    7 mi / 500 ft gain
    Hank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road.  I hiked from the south on this trip.  Follow the wide trail known as Hank's East trail marked with white blazes.  Soon you will reach a trail c...
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  • Rockaway, New Jersey

    Hike the Timberbrook Pond - Riley's Rise Loop

    5 mi / 500 ft gain
    The trailhead parking is at the end of Timberbrook Road, before the road enters Camp Winnebago (Boy Scouts). I hiked this in a clockwise directions starting on the Timberbrook Trail (yellow markers).  After about 1 mile the trail ends at a junction with the Four Birds Trail (white markers).  Turn...
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  • Patchogue, New York

    Camp at Fire Island's Watch Hill

    4.0
    2 mi
    If departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...
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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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  • 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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  • 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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