Top Trail Towns: Boston, MA

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Local trail runner and race director Josh Katzman explains it best: “Boston is steeped in history–this is where the American Revolution was born. You may be running past the site of the Boston Tea Party and stations on the Underground Railroad one day, and the next you could be at the site of the ‘shot heard ’round the world,’ standing at the spot Paul Revere was captured by the British and running around Thoreau’s Walden Pond.” In Boston, you can take your American history class on the run!

And if 400 years of history doesn’t make you pull the trigger on a Boston-based running adventure, then its trails might. “You can step out the door and be on a great trail within a mile,” says Katzman. Setting aside green, undeveloped areas has long been a part of the city’s ethic: more than 100 years ago, Frederick Law Olmsted designed Boston’s “Emerald Necklace,” a near-circle of parks with green-space connectors—a bejeweled chain draped about the city. And beyond the city limits and into Greater Boston, there are even more parks promising solitude and singletrack.


> Walden Pond State Reservation / Says Katzman of the park located in Concord, a suburb 20 miles northwest of Boston, “Here you can connect to the area’s deep history by visiting the ruins of Henry David Thoreau’s cabin, where he lived and wrote Walden.” It’s a peaceful two miles on the dirt path around the pond, and the reservation has other singletrack and doubletrack, too.

> Skyline Trail in the Blue Hills Reservation / From the park headquarters (15 miles south of Boston’s city center), it’s 15 miles out-and-back on the blue-blazed trail. “This is probably the easiest trail to follow in the reservation, but it is tough!” says Katzman. “Want to experience what trail training around Boston is like? Then run this trail–you’ll see how our short, technical ups and downs can wear you down.” From the ridge top, catch views of the Boston skyline and Atlantic Ocean.


> Stone Cat Trail Races / Taking place in the fall about 30 miles northeast of Boston proper, the marathon and 50-mile races are held on a rolling 12.5-mile loop, with lots of rocks and some roots thrown in.

> Trail Animals Running Club Trail Series / The Trail Animals hold more than a dozen races ranging from 10K to 100 miles in green spaces in and around Boston throughout the year.


> Get There / Logan International Airport serves up Boston to the world. Between trains, subways, buses and water ferries, the city and its ’burbs are well connected via public transport. Many trails are accessible via a short pavement run from public transport, and car-share companies can provide a set of wheels for a day trip to farther-off trailheads.

> Play Tourist / Take a day to explore all or part of the Freedom Trail and its 16 historic sites either independently or on a guided tour, to see landmarks like the Boston Common, Paul Revere’s home and the site of the Boston Massacre. All the sites are linked in a 2.5-mile route that you can, hypothetically, run.

> Take Note / Boston’s Trail Animals Running Club (TARC) is nearing 4,000 members. Explains member Katzman, “A couple years ago we had one runner tell us it was hard to figure out what exactly a TARC event was–a race, or some sort of crazy family reunion. When we heard that, we knew we were on the right path for being stewards of trail culture as the sport grows.” Connect with TARC on their Facebook page.


1630 Year Boston was founded, making it one of the oldest cities in the United States.

125 Number of trail miles in the 7,000-plus-acre Blue Hills Reservation,  south of Boston, a focal point of local trail running.

1878 Year Frederick Law Olmsted started designing Boston’s Emerald Necklace.

This article originally appeared in our December 2015 issue.

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