The City on the Hills - Boston (MA)
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.