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The Best Hiking in Madison

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

Top hiking spots in and near Madison

  • Madison, Connecticut

    Hike Madison Hammonasset Trail

    3.3 mi / 36 ft gain
    Madison Hammonasset Trail is a 3.3 mile out and back hike where you may see beautiful wild flowers located near Madison, Connecticut.
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  • Guilford, Connecticut

    Hike East River Preserve Loop Trail

    3.2 mi / 164 ft gain
    East River Preserve Loop Trail is a 3.2 mile loop hike that takes you by a lake located near Guilford, Connecticut.
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  • Madison, Connecticut

    Hike Meig's Point

    1.4 mi / 36 ft gain
    Meig's Point is a 1.4 mile out and back hike where you may see beautiful wild flowers located near Madison, Connecticut.
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  • Killingworth, Connecticut

    Hike Papermill Trail

    1.4 mi / 95 ft gain
    Papermill Trail is a 1.4 mile out and back hike where you may see beautiful wild flowers located near Killingworth, Connecticut.
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  • Guilford, Connecticut

    Hike New England Trail (Net)

    207.3 mi / 31 ft gain
    New England Trail (NET) is a 207.3 mile point-to-point hike that takes you by a lake located near Guilford, Connecticut.
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  • Clinton, Connecticut

    Hike Brook, Laurel Ridge And Princess Pine Trail Loop

    1.2 mi / 160 ft gain
    Brook, Laurel Ridge and Princess Pine Trail Loop is a 1.2 mile loop hike that takes you past scenic views located near Clinton, Connecticut.
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  • Clinton, Connecticut

    Hike Bougie, Laurel Ridge And Princess Pine Trail Loop

    1 mi / 124 ft gain
    Bougie, Laurel Ridge and Princess Pine Trail Loop is a 1 mile loop hike that takes you past scenic views located near Clinton, Connecticut.
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  • Guilford, Connecticut

    Hike Lost Lake White Trail

    6.7 mi / 800 ft gain
    Lost Lake White Trail is a 6.7 mile loop hike that takes you by a lake located near Guilford, Connecticut.
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  • Guilford, Connecticut

    Hike West Woods Loop Trail

    2.1 mi / 200 ft gain
    West Woods Loop Trail is a 2.1 mile loop hike that takes you by a lake located near Guilford, Connecticut.
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  • Killingworth, Connecticut

    Hike Lake Hammo Loop Trail

    5.8 mi / 452 ft gain
    Lake Hammo Loop Trail is a 5.8 mile loop hike where you may see beautiful wild flowers located near Killingworth, Connecticut.
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  • Guilford, Connecticut

    Hike Westwoods Trail

    6.1 mi / 646 ft gain
    Westwoods Trail is a 6.1 mile loop hike where you may see beautiful wild flowers located near Guilford, Connecticut.
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  • Guilford, Connecticut

    Hike Orange And Blue Loop

    1.4 mi / 127 ft gain
    Orange and Blue Loop is a 1.4 mile loop hike that takes you past great forest setting located near Guilford, Connecticut.
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  • Guilford, Connecticut

    Hike Timberlands Preserve Loop From Lakeside Drive

    1.9 mi / 203 ft gain
    Timberlands Preserve Loop from Lakeside Drive is a 1.9 mile loop hike that takes you by a lake located near Guilford, Connecticut.
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  • Killingworth, Connecticut

    Hike Chatfield Hollow Loop

    2.3 mi / 433 ft gain
    Chatfield Trail Loop is a 2.3 mile loop hike that takes you past great forest setting located near Killingworth, Connecticut.
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  • Killingworth, Connecticut

    Hike Upper And Lower Chatfield Trail

    7.4 mi / 974 ft gain
    Upper and Lower Chatfield Trail is a 7.4 mile loop hike that takes you by a lake located near Killingworth, Connecticut.
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  • Killingworth, Connecticut

    Hike White Blazes

    1.7 mi / 357 ft gain
    Chatfield Hollow White Blazes is a 1.7 mile loop hike that takes you past great forest setting located near Killingworth, Connecticut.
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