The Best Running in Boston

Looking for the best running 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 running 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

    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

    Run the Jamaica Pond and Victorian Jamaica Plain Loop

    5.0
    1.5 mi / 95 ft gain
    Park in the Jamaica Pond parking area. You can go either direction on this loop trail, which is highly trafficked and dog-friendly. Keep a lookout for (and a respectful distance from) the wildlife that live here. The loop around Jamaica Pond itself is 1.5 miles. The best part about running in thi...
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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

    Paul Revere Ride to Freedom Bike Tour

    45.67 mi / 1480 ft gain
    Paul Revere Ride to Freedom Bike Tour is a loop trail that is moderately difficult located near Boston, Massachusetts.
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  • Cambridge, Massachusetts

    Bike or Run on the Charles River Path

    10 mi
    The Charles River Path becomes a center of activity in Boston, especially during the summer, and you can run (or bike) it! It is a paved pathway that travels along both sides of the Charles River from the North End of the city to Allston and beyond. There are several bridges along the way with pe...
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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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  • Brookline, Massachusetts

    Brookline Stairways and Paths

    2.97 mi / 52 ft gain
    Brookline Stairways and Paths is a loop trail that takes you by the lake located near Brookline, Massachusetts.
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  • Brookline, Massachusetts

    Brookline Reservoir

    0.92 mi / 89 ft gain
    Brookline Reservoir is a loop trail that takes you by the lake located near Brookline, 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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  • 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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  • Cambridge, Massachusetts

    Fresh Pond Reservation Loop Trail

    2.5 mi / 59 ft gain
    Fresh Pond Reservation Loop Trail is a loop trail that takes you by the lake located near Cambridge, Massachusetts.
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