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The Best Hiking in Boston

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

Top hiking spots in and near Boston

  • Boston, Massachusetts

    Public Garden Monument Walking Tour

    1.18 mi / 43 ft gain
    Public Garden Monument Walking Tour is a loop trail that takes you by the lake located near Boston, Massachusetts.
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  • Boston, Massachusetts

    Commonwealth Ave Monument Tour

    2.17 mi / 20 ft gain
    Commonwealth Ave Monument Tour is an out-and-back trail where you may see beautiful wildflowers located near Boston, Massachusetts.
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  • Boston, Massachusetts

    Boston City View Bike Route

    10.1 mi / 413 ft gain
    Boston City View Bike Route is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.
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  • Boston, Massachusetts

    Franklin Park

    2.26 mi / 164 ft gain
    Franklin Park is a loop trail that takes you by the lake located near Dorchester, Massachusetts.
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  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...
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  • Boston, Massachusetts

    Charles River Short Bike Loop Trail

    3.45 mi / 33 ft gain
    Charles River Short Bike Loop Trail is a loop trail that takes you by a river located near Cambridge, Massachusetts.
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  • Boston, Massachusetts

    Exploring Boston's North End

    4.91 mi / 266 ft gain
    Exploring Boston's North End is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.
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  • Cambridge, Massachusetts

    Charles River Reservation Full Bike Loop

    28.2 mi / 745 ft gain
    Charles River Reservation Full Bike Loop is a loop trail where you may see beautiful wildflowers located near Cambridge, Massachusetts.
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  • Boston, Massachusetts

    Jamaica Pond

    1.46 mi / 36 ft gain
    Jamaica Pond is a loop trail that takes you past scenic surroundings located near Boston, Massachusetts.
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  • Boston, Massachusetts

    Boston Harbor and Castle Island

    2.2 mi / 98 ft gain
    Boston Harbor and Castle Island is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.
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  • Boston, Massachusetts

    Run the Arnold Arboretum Trail

    5.0
    2.6 mi / 150 ft gain
    Park in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...
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  • Cambridge, Massachusetts

    Harvard Yard Tour

    1.76 mi / 56 ft gain
    Harvard Yard Tour is a loop trail where you may see beautiful wildflowers located near Cambridge, Massachusetts.
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  • Boston, Massachusetts

    Chestnut Hill Reservoir Trail

    1.6 mi / 69 ft gain
    Chestnut Hill Reservoir Trail is a loop trail that takes you by the lake located near Chestnut Hill, Massachusetts.
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  • Cambridge, Massachusetts

    Mount Auburn Loop

    1.42 mi / 128 ft gain
    Mount Auburn Loop is a loop trail that takes you through a nice forest located near Cambridge, Massachusetts.
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  • Cambridge, Massachusetts

    Mount Auburn Cemetery Trail

    3.15 mi / 279 ft gain
    Mount Auburn Cemetery Trail is a loop trail where you may see beautiful wildflowers located near Watertown, Massachusetts.
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  • Newton, Massachusetts

    Hammond Pond and Webster West

    2.57 mi / 292 ft gain
    Hammond Pond and Webster West is a loop trail that takes you by the lake located near Chestnut Hill, Massachusetts.
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