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Litchfield County, Connecticut

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

Top Chillin Spots in and near Litchfield County

  • Glastonbury, Connecticut

    Hike the Cotton Hollow Nature Preserve

    5.0
    3 mi
    There are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...
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  • Middlesex County, Connecticut

    Hike to Glen Falls

    5.0
    0.75 mi
    Accessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...
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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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  • Glastonbury, Connecticut

    Blackledge Falls

    4.0
    1.46 mi / 207 ft gain
    Although the park contains hiking trails, a pond and a streambelt, the primary draw of this parcel of land is the 25 foot waterfall. The falls flow varies depending on the volume of precipitation, from a trickle in the dry months to a three-pronged vertical drop after some consistent snow melt or...
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  • Cold Spring, New York

    Photograph Indian Brook Falls

    2.8
    This is about as short a walk and as little effort as you can put in for a beautiful waterfall. You can barely call it a hike, but I'll list it as such since you do walk through the woods for 5 minutes. The trail is extremely well built, and is pretty easily accessible through the winter.The trai...
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  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • Gardiner, New York

    Hike the Overcliff - Undercliff Road Loop

    5.3 mi / 350 ft gain
    From the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk.  The trail connects the parking lot to the Overcliff Road/Undercliff Road junction.  The loop can be done in either direction.  I turned left on the Overcliff Road.  This takes you behind...
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  • Elka Park, New York

    Hike to Huckleberry Point

    4.5
    4.5 mi / 644 ft gain
    This is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...
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  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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  • Elka Park, New York

    Backpack the Eastern Half of Devil's Path in the Catskill Mountains

    5.0
    14 mi / 3900 ft gain
    The Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...
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