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The Best Hiking in New Fairfield

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

  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
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  • New Fairfield, Connecticut

    Hike Great Hollow And Lower Overlook Loop

    4 mi / 800 ft gain
    Great Hollow and Lower Overlook Loop is a 4 mile loop hike that takes you by a river located near New Fairfield, Connecticut.
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  • New Fairfield, Connecticut

    Hike Pootatuck State Forest Loop

    1.8 mi / 259 ft gain
    Pootatuck State Forest Loop is a 2 mile loop hike that takes you by a lake located near New Fairfield, Connecticut.
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  • New Fairfield, Connecticut

    Hike Pine Hill Road Loop

    1.9 mi / 291 ft gain
    Pine Hill Road Loop is a 1.9 mile loop hike where you may see beautiful wild flowers located near New Fairfield, Connecticut.
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  • New Fairfield, Connecticut

    Hike Great Hollow Main Loop

    2.4 mi / 288 ft gain
    Great Hollow Main Loop is a 2.4 mile loop hike that takes you by a waterfall located near New Fairfield, Connecticut.
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  • Danbury, Connecticut

    Hike Boggs Pond Red Trail Loop

    3.4 mi / 600 ft gain
    Boggs Pond Red Trail Loop is a 3.4 mile loop hike that takes you by a lake located near Danbury, Connecticut.
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  • Brookfield, Connecticut

    Hike Still River Greenway: Arthur Harris Linear Park

    3.3 mi / 131 ft gain
    Still River Greenway: Arthur Harris Linear Park is a 3.3 mile loop hike that takes you by a river located near Brookfield, Connecticut.
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  • Brookfield, Connecticut

    Hike Williams Gurski Open Space Trails Via Williams Park

    3 mi / 462 ft gain
    Williams-Gurski Open Space Trails via Williams Park is a 3 mile loop hike that takes you past great forest setting located near Brookfield, Connecticut.
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  • Danbury, Connecticut

    Hike Parks Pond Loop

    1.3 mi / 137 ft gain
    Parks Pond Loop is a 1.3 mile loop hike that takes you by a lake located near Danbury, Connecticut.
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  • Danbury, Connecticut

    Hike Tarrywile Park Trail

    4.5 mi / 964 ft gain
    Tarrywile Park Trail is a 4.5 mile out and back hike that takes you by a lake located near Danbury, Connecticut.
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  • Danbury, Connecticut

    Hike Blue And Parks Pond Loop

    1.7 mi / 288 ft gain
    Blue and Parks Pond Loop is a 1.7 mile loop hike that takes you by a lake located near Danbury, Connecticut.
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  • Danbury, Connecticut

    Hike Terrywile Park Yellow Loop

    3.6 mi / 967 ft gain
    Terrywile Park Yellow Loop is a 3.6 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
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  • Danbury, Connecticut

    Hike Middle Mountain To Thomas Mountain Loop

    3.7 mi / 856 ft gain
    Middle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
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  • Bridgewater, Connecticut

    Hike Iron Ore Hill Red And Blue Loop

    2.5 mi / 459 ft gain
    Iron Ore Hill Red and Blue Loop is a 2.5 mile loop hike that takes you by a lake located near Bridgewater, Connecticut.
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  • Ridgefield, Connecticut

    Hike Shadow Lake Trail

    0.7 mi / 26 ft gain
    Shadow Lake Trail is a 0.7 mile loop hike that takes you by a river located near Ridgefield, Connecticut.
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  • New Milford, Connecticut

    Hike Waramaug Loop

    1.2 mi / 180 ft gain
    Waramaug Loop is a 1.2 mile loop hike that takes you by a river located near New Milford, Connecticut.
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