East Boston After Dark: Walking City Trail Night Hike on Monday

Meet fellow urban hikers and enjoy dreamy views of Downtown Boston and the harbor on a 2.7-mile hike from Suffolk Downs Station to Belle Isle Marsh and Orient Heights (plus optional drinks at Renegade’s Pub!)
Boston is a city of trails…and urban hikers. What better way to meet fellow city ramblers than by going on an adventure together during the magic hour? After their inaugural winter run in early 2024, Boston Night Hikes are back for the summer! Hosted by me, Miles Howard (founder and lead organizer of Boston’s Walking City Trails), these free group hikes are a unique way to discover Boston’s natural and built beauty while connecting with residents and city visitors.
On this 2.7-mile hike, we’ll meet in the MBTA’s Suffolk Downs Blue Line station by the main entrance off of Bennington Street at 6pm on August 18. We’ll venture into Belle Isle Marsh for a stunning view of Downtown Boston and the harbor through the reeds. And then we’ll climb streets and stairs to nearby Orient Heights for another Boston vista before descending to the Orient Heights Blue Line station, with the option to grab drinks nearby at Renegade’s Pub.
The hike will include a mixture of paved paths, dirt paths, and stairs. While difficulty is subjective, the distance and alternately flat and sloped terrain make this one an easy-to-moderate hike.
There’s no signup cost for Boston Night Hikes, though Walking City Trail donations are still enormously helpful and appreciated! And all you need to do is RSVP below. There’s also no group size cap for these hikes, so if your plans change and you can’t make it, don’t sweat it. There will be more Night Hikes in the future.
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.


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