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The Best Hiking in Greenwich

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

Top hiking spots in and near Greenwich

  • Greenwich, Connecticut

    Hike Montgomery Pinetum Loops

    4.1 mi / 377 ft gain
    Montgomery Pinetum Loops is a 1.9 mile loop hike that takes you by a lake located near Cos Cob, Connecticut.
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  • Greenwich, Connecticut

    Hike Tod's Point

    2.6 mi / 29 ft gain
    Tod's Point is a 2.6 mile loop hike that takes you past scenic views located near Old Greenwich, Connecticut.
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  • Stamford, Connecticut

    Hike Ridge Run Trail To River Road Loop

    2.5 mi / 255 ft gain
    Ridge Run Trail to River Road Loop is a 2.5 mile loop hike that takes you by a river located near Stamford, Connecticut.
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  • Stamford, Connecticut

    Hike Mianus Maze Trail

    4.8 mi / 341 ft gain
    Mianus Maze Trail is a 4.9 mile loop hike that takes you by a river located near Stamford, Connecticut.
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  • Stamford, Connecticut

    Hike Riverwalk Trail To Indian Mill Trail Loop

    1.5 mi / 147 ft gain
    Riverwalk Trail to Indian Mill Trail Loop is a 1.5 mile loop hike that takes you past great forest setting located near Stamford, Connecticut.
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  • Stamford, Connecticut

    Hike Pine Hill Road And Meander Trail Loop

    2.6 mi / 147 ft gain
    Pine Hill Road and Meander Trail Loop is a 2.6 mile loop hike that takes you past great forest setting located near Stamford, Connecticut.
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  • Greenwich, Connecticut

    Hike Greenwich Audubon Center Trail

    2.3 mi / 200 ft gain
    Greenwich Audubon Center Trail is a 2.3 mile loop hike that takes you by a lake located near Greenwich, Connecticut.
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  • Greenwich, Connecticut

    Hike Lake Mead Loop

    1.6 mi / 167 ft gain
    Lake Mead Loop is a 1.6 mile loop hike that takes you past wildlife located near Greenwich, Connecticut.
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  • Greenwich, Connecticut

    Hike Old Pasture And Lake Loop

    3.1 mi / 383 ft gain
    Old Pasture and Lake Loop is a 3.1 mile loop hike that takes you by a lake located near Greenwich, Connecticut.
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  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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  • Scarsdale, New York

    Mamaroneck Reservoir via Yellow Trail Loop

    2.32 mi / 82 ft gain
    Mamaroneck Reservoir via Yellow Trail Loop is a loop trail that takes you by a river located near Mamaroneck, New York.
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  • Darien, Connecticut

    Hike Woodland Park Loop

    1.5 mi / 78 ft gain
    Woodland Park Loop is a 1.5 mile loop hike that takes you past wildlife located near Darien, Connecticut.
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  • North Castle, New York

    Cranberry Lake Red, Purple and Yellow Loop

    1.75 mi / 184 ft gain
    Cranberry Lake Red, Purple and Yellow Loop is a loop trail that takes you by a lake located near West Harrison, New York.
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  • White Plains, New York

    Kensico Dam Staircase Loop

    1.07 mi / 190 ft gain
    Kensico Dam Staircase Loop is a loop trail that takes you by a lake located near Valhalla, New York.
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  • Armonk, New York

    Betsy Sluder Nature Trail

    1.7 mi / 259 ft gain
    Betsy Sluder Nature Trail is a loop trail that provides a good opportunity to view wildlife located near Armonk, New York.
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