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

  • Gardiner, New York

    Hike the Dickie Barre, Peters Kill and Awosting Falls Loop

    3.0
    7.8 mi
    This loop hike takes you to Awosting Falls (65 ft.), as well as to great  valley views along the ridge of Dickie Barre, and across Peters Kill, on the way.Start out on West Trapps Connector Trail (yellow blazes) at the east end of the West Trapps parking lot (get their early because the lot will ...
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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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  • 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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  • Woodcliff Lake, New Jersey

    Wood Dale Park Loop

    4.0
    0.38 mi / 16 ft gain
    Located within the Wood Dale County Park in Woodcliff Lake, New Jersey, the Wood Dale Park Loop offers visitors a tranquil walking experience amidst lush greenery and a picturesque pond. This family-friendly loop is ideal for leisurely strolls, jogging, and nature observation. Trail Overview ...
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  • Norfolk, Connecticut

    Campbell Falls

    4.0
    0.99 mi / 161 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • Closter, New Jersey

    Hike to Huyler's Landing/ Closter Dock Loop

    4.0
    5.4 mi / 450 ft gain
    The easiest way to access this loop hike is by parking at the Palisades State Park Headquarters.  This is just off exit 2 from the Palisades Interstate Parkway.  Parking here is free and it is a short walk down a road to the Closter Dock Trail.  The Closter Dock Trail is more of a wide fire road ...
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  • Gardiner, New York

    Gertrude's Nose

    4.9
    6.97 mi / 919 ft gain
    It would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...
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  • Gardiner, New York

    Millbrook Mountain & Gertrude Nose loop

    8.77 mi / 1253 ft gain
    This great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...
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  • Gardiner, New York

    Lake Minnewaska Loop Trail

    2.01 mi / 348 ft gain
    Lake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.
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  • Sheffield, Massachusetts

    Race Brook Falls

    4.0
    2.47 mi / 1145 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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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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  • Mount Washington, Massachusetts

    Guilder Pond and Mount Washington Lookout Trail

    3.92 mi / 909 ft gain
    Guilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.
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  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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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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  • Mount Washington, Massachusetts

    Bash Bish Falls

    4.3
    0.75 mi / 295 ft gain
    Bash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...
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  • Copake, New York

    Bash Bish Falls from Taconic State Park

    1.53 mi / 167 ft gain
    Bash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York. Swimming is not permitted at Bash Bish Falls. 
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