Boston Walking City Trails

About This Challenge

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.