Running 31 miles from the Charles River at Millennium Park to Castle Island at Boston Harbor, the City On The Hills Trail is the east-to-west sibling of Boston’s Walking City Trail. It features over 40 green spaces spread across 9 Boston neighborhoods, while visiting some of the highest points in the city—a literal escalation from the Walking City Trail, with more elevation gain and mileage, but the same ease of access to public transit along the way. It was created between late 2023 and spring of 2025 by the same Boston ramblers who established the Walking City Trail.
The City On The Hills Trail is 31.1 miles long with around 1,800 feet of vertical elevation gain from start to finish. The trail surfaces include sidewalks, dirt paths, gravel paths, rocky and rooty paths, stairs, boardwalk segments, and bridges. Section 1 is the longest section of the trail, Section 2 is the hilliest and shortest section of the trail, and Section 5 is the most level section of the trail (but there are still a few hills).
https://www.bostontrails.org/cityonthehillstrail
