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New Fairfield, Connecticut

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

Top Hiking Spots in and near New Fairfield

  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Carpenter's Grove Loop

    4.0
    4 mi / 400 ft gain
    This loop hike can be started from several different places.  I chose to start from Allison Park which overlooks the Hudson River in Englewood Cliffs, NJ.  From the parking area, walk out to the entrance road and travel south to Saint Peter's College.  The Long Path Trail, which you join from All...
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  • West Milford, New Jersey

    Hike Bearfort Mountain

    5.0
    5.06 mi / 1007 ft gain
    Bearfort Mountain is a great weekend morning hike that borders NJ and NY. Parking can be tricky as the entrance to the lot looks like it is Greenwood Lake Marina's boat storage area. Once parked, find the trail entrance at the top of the little hill and continue to the blue on white marked trail....
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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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  • 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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