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

  • 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

    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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  • New York, New York

    Jacqueline Kennedy Onassis Reservoir Running Path

    5.0
    1.68 mi / 69 ft gain
    Jacqueline Kennedy Onassis Reservoir Running Path is a loop trail that takes you by a lake located near New York City, New York.
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  • Ridgewood, New Jersey

    Saddle River Trail

    5.0
    Saddle River Trail is an out-and-back trail that takes you by a lake located near Fair Lawn, New Jersey.
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  • New York, New York

    Northwest Central Park Loop

    3.63 mi / 164 ft gain
    The Northwest Central Park Loop in New York City offers a scenic, family-friendly experience through some of the park’s quieter sections. The loop features well-maintained paths, stunning views of the surrounding nature, and landmarks like the Reservoir. It’s perfect for walking, jogging, or ca...
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  • Allendale, New Jersey

    Celery Farm Mayor Fitzpatrick Nature Trail

    3.0
    1.2 mi / 92 ft gain
    The Celery Farm Mayor Fitzpatrick Nature Trail in Allendale, New Jersey, is a peaceful, scenic retreat for birdwatchers, hikers, and nature lovers. This 1-mile loop trail winds through a 107-acre freshwater wetland preserve, offering opportunities to spot over 240 bird species, deer, turtles, a...
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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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  • New Windsor, New York

    Jessup/West Ridge Loop via the Sweet Clover Trail

    9.17 mi / 1916 ft gain
    Schunnemunk Mountain State Park is one of my favorite parks.  It offers many trails and possibilities for different loops.  The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions. This hike starts at the Taylor Road par...
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  • Meriden, Connecticut

    Higby Mountain Trail

    2.11 mi / 486 ft gain
    The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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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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  • 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

    4.8
    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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