I’m walking, here!
Boston Walking City Trails has launched a brand new hiking trail! The City on the Hills Trail is a 31-mile adventure through some of the best parts of the city. And because we love a good walk (especially if there’s a view and maybe a snack involved), we’re breaking it all down for you, section by section.
First up: Section 5
Starting at the Savin Hill Red Line station, Section 5 winds 6.4 miles through Dorchester and Southie, finishing up at the iconic Castle Island. Even though it’s technically the last leg of the trail, the first half feels like a bit of an escape, not a ton of T stops or coffee shops until you get closer to Dorchester Heights and make your way into Southie proper. (Pro tip: Plan your pit stops ahead of time.)
You can catch the start, middle, or end by hopping on the Red Line or grabbing a bus — easy peasy.
As for the views? Think sweeping sights of Dorchester Bay from Savin Hilltop, the salty air and breezy vibes of the Harborwalk around the UMASS Boston campus, and of course, the iconic stroll across the causeway to Castle Island. Pack some sunscreen, lace up your sneakers, and let’s get moving!
Visit here for full trail maps!
Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.
