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The Best Hiking in New Milford

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

Top hiking spots in and near New Milford

  • New Milford, Connecticut

    Hike New Milford Reservoir Loop

    1.2 mi / 75 ft gain
    New Milford Reservoir Loop is a 1.2 mile loop hike that takes you by a lake located near New Milford, 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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  • New Milford, Connecticut

    Hike Housatonic River Trail

    10.1 mi / 413 ft gain
    Housatonic River Trail is a 10.1 mile out and back hike that takes you by a river located near New Milford, Connecticut.
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  • New Milford, Connecticut

    Hike River Road Pond Loop

    2.7 mi / 183 ft gain
    Sega Meadows Park Loop is a 2.6 mile loop hike that takes you by a river located near New Milford, Connecticut.
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  • Roxbury, Connecticut

    Hike Roxbury Mines

    3.6 mi / 511 ft gain
    Roxbury Mines is a 3.6 mile loop hike where you may see beautiful wild flowers located near Roxbury, Connecticut.
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  • Washington, Connecticut

    Hike Pinney Loop Trail

    3.7 mi / 341 ft gain
    Pinney Loop Trail is a 3.7 mile loop hike that takes you by a river located near Washington Depot, Connecticut.
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  • Washington, Connecticut

    Hike Green Circle Trail

    4.2 mi / 521 ft gain
    Yellow Circle Blazes Loop is a 4.2 mile loop hike that takes you by a river located near Washington Depot, Connecticut.
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  • 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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  • 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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  • Roxbury, Connecticut

    Hike Shepaug River Trail

    3.6 mi / 705 ft gain
    Shepaug River Trail is a 3.6 mile out and back hike that takes you by a river located near Roxbury, 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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  • Roxbury, Connecticut

    Hike Brian E. Tierney Blue Trail

    1.8 mi / 275 ft gain
    Brian E. Tierney Blue Trail is a 1.8 mile loop hike that takes you by a waterfall located nearr Roxbury, Connecticut.
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  • Washington, Connecticut

    Hike Van Sinderen Loop

    3.4 mi / 469 ft gain
    Van Sinderen Loop is a 3.4 mile loop hike that takes you by a river located near Washington, Connecticut.
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  • Sherman, Connecticut

    Hike Appalachian Trail: Hoyt Road To Bull's Bridge

    7.9 mi / 1 ft gain
    Appalachian Trail: Hoyt Road to Bull's Bridge is a 8.5 mile out and back hike that takes you by a river located near Gaylordsville, 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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