Westport, Connecticut

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

Top Hiking Spots in and near Westport

  • Middletown, Connecticut

    Explore Wadsworth Falls

    5.0
    0.25 mi
    When it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...
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  • New York, New York

    Brooklyn Bridge Walk

    5.0
    2.4 mi / 26 ft gain
    Brooklyn Bridge Walk is an out-and-back trail that takes you by a river located near New York City, New York.
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  • Brooklyn, New York

    Brooklyn Bridge Walk via Brooklyn

    4.7
    1.12 mi / 0 ft gain
    Walking the Brooklyn Bridge from the Brooklyn side is a rewarding experience that blends history, architecture, and stunning views of New York City. Start your journey at the pedestrian entrance near Cadman Plaza, which is easily accessible by subway (Court Street or High Street stations). The br...
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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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  • Brooklyn, New York

    Brooklyn Botanical Gardens

    5.0
    1.34 mi / 75 ft gain
    Brooklyn Botanical Gardens is a loop trail that takes you by a lake located near New York City, New York.
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  • Brooklyn, New York

    Prospect Park Loop

    4.7
    3.65 mi / 223 ft gain
    There are multiple places to enter Prospect Park. If you're looking for the main entrance to Prospect Park, it faces the stunning Soldiers' and Sailors' Arch in Grand Army Plaza. It is adjacent to the Brooklyn Botanical Garden, the flagship Brooklyn Public Library, and the Brooklyn Museum. As you...
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  • Tuxedo Park, New York

    Sterling Lake & Fire Tower Loop

    5.0
    7.54 mi / 1239.06 ft gain
    Start out by turning right when you walk out of the visitor center onto Sterling Lake Loop (Blue Blazes). The visitor center is worth going in as they have a full diorama of the park with LED light to show trail routes. About .3 miles into the hike you will cross over a small bridge with a waterf...
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  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • Cedar Grove, New Jersey

    Hike at Mills Reservation

    4.7
    2 mi / 200 ft gain
    Mills Reservation is over 150 acres of wooded area located off of Normal Ave. near the Cedar Grove reservoir. Parking space is limited due to the small size but there is another hidden lot towards the back if you make a right out of the parking lot and then the first right turn onto Highland Ave....
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