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The Best Hiking in Monroe

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

Top hiking spots in and near Monroe

  • Oxford, Connecticut

    Hike Pomperaug Trail

    3.7 mi / 856 ft gain
    Pomperaug Trail is a 4.5 mile loop hike that takes you by a river located near Oxford, Connecticut.
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  • Newtown, Connecticut

    Hike Zoar Trail

    6.1 mi / 1 ft gain
    Zoar Trail is a 7.0 mile loop hike that takes you by a lake located near Stevenson, Connecticut.
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  • Monroe, Connecticut

    Hike Webb Mountain Yellow/Orange/Red Loop

    1 mi / 157 ft gain
    Webb Mountain Yellow/Orange/Red Loop is a 2.7 mile loop hike that takes you by a river located near Monroe, Connecticut.
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  • Monroe, Connecticut

    Hike Webb Mountain Trail

    1.6 mi / 118 ft gain
    Webb Mountain Trail is a 1.6 mile loop hike that takes you past great forest setting located near Monroe, Connecticut.
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  • Oxford, Connecticut

    Hike Jackson Cove

    1.1 mi / 167 ft gain
    Jackson Cove is a 1.2 mile out and back hike that takes you by a river located near Oxford, Connecticut.
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  • Oxford, Connecticut

    Hike Rockhouse Hill Sanctuary Loop

    4.6 mi / 643 ft gain
    Rockhouse Hill Sanctuary Loop is a 4.6 mile loop hike that takes you past wildlife located near Oxford, Connecticut.
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  • Southbury, Connecticut

    Hike Pomperaug And Crest Trail Loop

    3.4 mi / 606 ft gain
    Pomperaug and Crest Trail Loop is a 3.4 mile loop hike that takes you by a river located near Oxford, Connecticut.
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  • Southbury, Connecticut

    Hike Miller Trail

    2.5 mi / 393 ft gain
    Miller Trail is a 2.5 mile loop hike where you may see beautiful wild flowers located near Southbury, Connecticut.
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  • Southbury, Connecticut

    Hike Pomperau Trail Loop

    1.6 mi / 285 ft gain
    Pomperau Trail Loop is a 1.6 mile loop hike that takes you past great forest setting located near Southbury, Connecticut.
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  • Shelton, Connecticut

    Hike Indian Well Trail

    1.4 mi / 380 ft gain
    Indian Well Trail is a 1.8 mile loop hike that takes you by a river located near Shelton, Connecticut.
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  • Ansonia, Connecticut

    Hike Fountain Lake Reservoir

    0.5 mi / 13 ft gain
    Fountain Lake Reservoir is a 0.5 mile loop hike that takes you by a lake located near Ansonia, Connecticut.
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  • Monroe, Connecticut

    Hike Housatonic Railway Trail: Monroe

    3 mi / 98 ft gain
    Housatonic Railway Trail: Monroe is a 3 mile out and back hike that takes you past great forest setting located near Monroe, Connecticut.
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  • Southbury, Connecticut

    Hike Southford Falls Red Trail

    1.7 mi / 252 ft gain
    Southford Falls Red Trail is a 1.7 mile loop hike that is rated as moderate located near Southbury, Connecticut.
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  • Newtown, Connecticut

    Hike Fairfield Hills Loop

    2.6 mi / 160 ft gain
    Fairfield Hills Loop is a 2.6 mile loop hike that takes you past great forest setting located nearr Newtown, Connecticut.
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  • Newtown, Connecticut

    Hike Al's Trail: Deep Brook Preserve

    2.9 mi / 213 ft gain
    Al's Trail: Deep Brook Preserve is a 2.9 mile loop hike that takes you by a river located near Newtown, Connecticut.
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  • Newtown, Connecticut

    Hike Rocky Glen Yellow And White Trail Loop

    1 mi / 209 ft gain
    Rocky Glen Yellow and White Trail Loop is a 1 mile loop hike that takes you by a river located near Sandy Hook, Connecticut.
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