A local's guide to where to run in Boston
- 15 April 2025
Tough.
That's how Dan Fitzgerald, Nike Run Coach and co-founder of Heartbreak Hill Running Company, describes the running community in Boston.
In a city that endures some of the most excruciating winters and sticky-hot summers, local runners meet the thrills of Mother Nature with grit, passion, endurance and joy as they hit the streets to rack up miles regardless of what's happening outside. On any given day, whether you're running near Boston's South End or its Esplanade, you'll encounter dozens, if not hundreds, of fellow runners along the way—rain or shine, sun or ice. "Tough" is a testament to the conditions people endure, says Dan, but also the strength and dedication it takes to run paths like Heartbreak Hill, an iconic incline on the city's marathon route that tests body and mind.
Together with Nike, Heartbreak has created running experiences that range from training runners for marathons to celebrating the culture of the sport through art, music and food in their physical stores in Chicago, Boston and, soon, Los Angeles, where Heartbreak will open a new shop this year. The thread that connects everything together: if you run, you belong.
And while, yes, running in Boston may be tough, that doesn't mean it isn't fun. You'll discover beautiful views, historic streets and a passion for sports that feels second to none. Below you'll find routes and recommendations from Nike Run Coach Dan and other die-hard runners at Heartbreak that will help you make the best of your time in Beantown.
"Our job is to connect with running and the running community. I want athletes to show up and just be themselves and be a runner".
Dan Fitzgerald, Nike Coach & Heartbreak co-founder
Enjoy Boston's Esplanade, a public park inspired by the waterways of Venice. Cross over the Longfellow Bridge to Cambridge past MIT and take in sweeping views of boats on the Charles River, the skyline and all the charms of a small city. Boston's tight geographic footprint is an advantage when you can take it all in on a 4-miler. "I love this route—it's super cool to see how many people are constantly running when you go more central-downtown", says Cate Schultz, who runs regularly with the Heartbreakers and is training to run Boston in 2025.
Call this the full tour of the city centre areas. You'll get the South End (not Southie, but you'll also go by there), the waterfront, the North End, the Rose Kennedy Greenway, the Garden (home of the Celtics), the locks at the end of the Charles River and Charlestown with views of MIT, then you'll gallop across the Back Bay. You can say you've seen the heart of Boston running if you rock this one.
"Plenty of bridges let you control the distance, and you get that sweet mix of cityscape and nature", say Rafe and Taylor Ann Gangi, a married couple who runs with Heartbreak, about the Esplanade route. "There are always plenty of other runners out there too, which is encouraging".
Run this route
This is Heartbreak Hill Running Company's signature route. A test and measure of distance athletes, the Firehouse is now the foundation of Heartbreak's training journey and looms large in the lore of the team, the Heartbreakers. According to Nike Run Coach Dan: "It's been a training cornerstone for legends like Bill Rodgers, my university distance runners, and all of the athletes training for Boston with us every weekend all winter long".
If you're looking for the best pastries in Boston, Heartbreak runners tell us this local franchise is the spot—and they say their coffee is amazing too. Flour Bakery & Cafe has nine locations throughout Boston for you to stop by after a morning run. Pro tip: Don't leave without trying the blueberry toaster pastry.
Located in Boston's South End, Toro offers delicious tapas to refuel after any type of run. Toro's menu includes everything from traditional small plates, like patatas bravas (fried, mildly spicy potatoes) and pan con tomate (bread with tomato), to a big paella that will ensure you get the protein and carbs you need after logging big miles.
Running can take a lot from you, mentally and physically, but a great milkshake, burger or cheese toastie sure can help. You'll find all of them at Roxie's Grilled Cheese, a Boston staple frequented by runners who are looking to refuel and hit up the restaurant's beloved arcade machines.
FoMu ice cream is a plant-based, allergy-kind joint that delivers big flavours and variety: a cookies and cream ice cream sundae, a chocolate chip ice cream sandwich and a scoop of pistachio almond milk ice cream, to name a few. FoMu's South End location is across from Heartbreak's shop, making it easy to treat yourself to dessert and new kicks.
It seems like almost everyone you talk to in Boston knows Anchovies. The dive bar specialises in an endless mix of drinks and cocktails and what the locals deem "good, cheap Italian food". Beyond the food and beverages, though, the energy at Anchovies is electric and contagious every day, which is why Boston runners love and swear by it.
If you're in Boston and want to join Nike Run Coach Dan and the Heartbreakers for a run, they meet on Thursday nights at 6:30pm at all their shops, Saturday mornings at 8am at their Newton location and Tuesday mornings at 6:34am at Reggie Lewis Center or MIT for track-running sessions. For more details on the schedule, check out heartbreak.run/boston to RSVP.
Photos by Boston-based photographer Tony Luong