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Westport, Connecticut

Top Spots in and near Westport

  • Tuxedo Park, New York

    Backpack Harriman State Park

    4.5
    18 mi / 1200 ft gain
    While the first day is a bit longer and less exciting in terms of frequent landmarks, its a relaxing hike through rocky, wooded, forest among bountiful blueberry bushes and the occasional raspberry bush. Enjoy the isolation on this leg. The second day is packed with frequent and beautiful landmar...
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  • Dover Plains, New York

    Hike Dover's Stone Church

    4.5
    Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
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  • New York, New York

    Visit the Vessel

    4.7
    Welcome to the newest neighborhood in the Manhattan West Side of New York, the Hudson Yards! After years of construction, the Vessel opened as a new centerpiece in the Hudson Yards on March of 2019. With 154 steel flights of stairs with 2,500 steps and 80 landings, you're walking adventures aroun...
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  • 608 Ramapo Valley Road, New Jersey

    Hike the Halifax Trail and Ruins in the Ramapo Valley Reservation

    8.25 mi / 500 ft gain
    To start, I recommend coming in the early morning or afternoon, as the parking lot fills up with people hiking, fishing or going for a walk with their family. I usually get my luckiest before 9. This park is as relaxing or exciting as you want to make it. Here is a good map to use/ print out. We ...
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  • Kent, Connecticut

    Hike the Ridge Loop Trail, Macedonia Brook SP

    3.0
    For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...
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  • New York, New York

    High Line

    4.6
    1.47 mi / 26 ft gain
    Built on a historic freight rail line and perched above the streets of Manhattan’s West Side, the High Line is a public park that features a green-lined walkway. Park hours depend on the season, although it never opens before 7am, so best to go for sunset. Although you may have some company on wa...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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  • Kent, Connecticut

    Explore Kent Falls

    5.0
    0.75 mi / 250 ft gain
    Every now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...
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  • Berlin, Connecticut

    Hike the Ragged Mountain Memorial Preserve

    4.5
    5.5 mi / 560 ft gain
    Ragged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds.  The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...
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  • 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

    Walk the George Washington Bridge at Sunset

    3.0
    0.9 mi
    Join the thousands of people who cross the GWB each day, but do it by foot! This is an easy walk with beautiful views of the New York City skyline. You will begin seeing signs for the bridge bike path at Ft. Washington St. & E. 177th St., which you follow for a few blocks until you begin asce...
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  • Brooklyn, New York

    Brooklyn Bridge Park Piers

    5.0
    1.5 mi
    Starting at the Brooklyn Main Street Park, you are on the right side of the Manhattan Bridge. Here you can check out the new outdoor climbing gym. Keep walking along the water and you'll soon come upon Pebble Beach. Now this beach is not exactly a "let's bring our beach chairs and spend the da...
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  • Brooklyn, New York

    Climb Outdoors at DUMBO Boulders

    5.0
    Enter at the corner of Adams St. and John St. and see the Manhattan Bridge above you. To your left is the new DUMBO Boulders, the largest outdoor rock gym in North America: at least for now.At only $9 for a day pass, includes the price of rental shoes, it's a steal compared to any gym in the cit...
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  • Brooklyn, New York

    Photograph Manhattan Bridge from Washington Street NYC

    4.7
    Located in DUMBO this is seen as one of of the prime photography spots in NYC for good reason. Off the intersection of Washington Street and Water Street is a perfect view of the Manhattan Bridge sandwiched between two buildings. If you want to take it one step further you are able to get a close...
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  • Brooklyn, New York

    Photograph the Brooklyn Bridge

    4.8
    Escaping the hustle and bustle of the city doesn't always require actually leaving the city. Hanging out next to the East River and focusing on photographing the Brooklyn Bridge can be just what you need to clear your head and get your fix for some outdoors time. This is a great spot to practice ...
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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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