National Directory of Trails / Massachusetts / Boston Trails

Arnold Arboretum

Arnold Arboretum is a 3 mile loop trail located near Boston, Massachusetts that features a lake and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 3 miles
  • Boston, MA

Battle Road Trail

3 mile long historic trail for running.


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  • 3 miles
  • Boston, MA

Charles River Esplanade

A 3.45 mile trail for runners.


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  • 3.45 miles
  • Boston, MA

Chestnut Hill Resevoir

A 1.75 mile loop for runners.


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  • 1.75 miles
  • Boston, MA

Jamaica Pond And Victorian Jamaica Plain

Jamaica Pond and Victorian Jamaica Plain is a 1.5 mile loop trail located in Boston, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 1.5 miles
  • Boston, MA

The Lexington Loop

A 30 mile loop for bikers mostly through back roads and woods.


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  • 30 miles
  • Boston, MA


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