Challenge
Boston, Massachusetts, United States
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The Boston Walking City Trails are a 58-mile urban hiking network connecting 75+ green spaces across 23 Boston neighborhoods. The network includes the original 27.4-mile Walking City Trail running from the Neponset River to Bunker Hill Monument, plus the 31.1-mile City On The Hills Trail from West Roxbury to Castle Island. These transit-accessible trails showcase Boston's parks, gardens, historic sites, and diverse neighborhoods while following the city's walkable heritage. Founded in spring 2022 by Bostonians with a shared passion for wandering, the trails can be completed in segments or as multi-day urban adventures, offering everything from Freedom Trail history to harbor views and hidden neighborhood gems.
Quick facts
Harvest River Bridge
Boston, Massachusetts
Sherrin Woods
Boston, Massachusetts
Stony Brook Reservation
Boston, Massachusetts
Sherman Street Green Space Conservancy
Boston, Massachusetts
Adams Park
Boston, Massachusetts
Arnold Arboretum
Boston, Massachusetts
Boston Walking City Trails covers 27 miles in total.
Most people complete Boston Walking City Trails in about 2-5 days.
The best season for Boston Walking City Trails is Anytime.
Boston Walking City Trails has 29 checkpoints to log on the way to finishing it.
Keep exploring
Short, finishable city walks across Boston, plus the trail guide that ties them together.