A Runner’s Guide to Boston: The World Major Marathon Cities

This is an unprecedented autumn in the history of running. Over the course of seven weeks this fall, five of the six World Marathon Majors are being held. All eyes will focus on Berlin, London, Chicago, Boston, and New York. In honor of this marathon-palooza, Great Runs is partnering with PodiumRunner on a series of running guides for each of these cities: A bit about their running culture, details on the best places to run, and marathon course highlights. Each guide will be published the week of that city’s marathon.

Boston: Monday, October 11 

As host of the world’s oldest marathon, headquarters of numerous running apparel and fitness tech companies, and home to 300,000 university students, Boston boasts a unique running culture and tradition. Boston is also a terrific city to run in, with its setting on the Charles River and the Atlantic Ocean, and pedestrian-scale historic neighborhoods. 

A few cautions about running in Boston: Winters can be cold and snowy, which might affect where you can run. Signage and wayfinding are notoriously poor, so it’s always helpful to have a map or phone. And the city’s creaky but functional public transport system, “The T”, can be very helpful in getting you to a plum running spot, or home. 

Here are some of our favorite places to run in Boston. 

Charles River Paths

Touring the banks of the Charles is one of the most iconic runs in the United States, with paths on both the Boston and Cambridge sides and numerous historic bridges allowing for routes of various lengths. We recommend heading west on the Boston side, then east on the Cambridge side, where you’ll run past Harvard and MIT and catch the best views of the river and the Boston skyline. A signature, approximate 10-mile loop goes from the Museum of Science to the JFK Bridge (Harvard University) and back. 

The Emerald Necklace

A greenway originally conceived by Frederick Law Olmsted, the Emerald Necklace is a loosely connected string of parks, creating a 10-mile run from the State House to Franklin Park, with few traffic crossings. Highlights along the bucolic route include Boston Common, the Public Garden, Commonwealth Ave. Mall, Fens, Jamaica Pond, Arnold Arboretum, and Franklin Park. 

Boston Waterfront

The ‘Harborwalk’ along Boston Harbor has been getting steadily better, with a growing network of pedestrian paths adding up to a 43-mile linear park along the water. It’s possible to run 14 continuous miles from Boston to Quincy, most of it along the water. A favorite section is in Charlestown, where you can run up to the Bunker Hill Monument, and then enjoy the HarborWalk past the USS Constitution and along the water, and even connect to the Charles River via a spectacular pedestrian bridge. 

South Boston Waterfront

Part of the Harborwalk, this run is often overlooked by visitors, but it’s worth the quick Uber ride from downtown to enjoy stunning oceanfront running. Start with a loop of Castle Island, and then head to the JFK Museum for beautiful water views the whole way. 

Historic Neighborhoods

Start with some hills on the gas-lamped streets of Beacon Hill, then enjoy the tony Back Bay neighborhood, combining the Comm Ave. Mall with the upscale shops of Newbury St. For a longer run, add the historic South End (not to be confused with South Boston), or a segment along the river. 

Hidden Gems and Unique Running Experiences

While the river, waterfront, Emerald Necklace, and historic neighborhoods make all the ‘best of Boston running’ lists, Boston also features some hidden gems that are worth the extra effort to get to. 

Take the Blue Line to the Airport Station to enjoy a fantastic run in East Boston, which has a spectacular running path and killer skyline views. It’s one of the loveliest runs you’ll ever do near an airport! Also nearby is Deer Island, which is the best run you’ll ever do around a waste treatment plant, using a 2.5-mile perimeter loop with 360° ocean views. 

In season, hop a ferry to Spectacle Island, part of Boston Harbor Islands National Park. Spectacle Island was ‘reborn’ as a park out of the clay and sediment from the Big Dig project, and features five miles of dirt trails over rolling hills, with great views of the water and the Boston skyline.

Not surprisingly, history buffs can also find great running routes in this legendary city. The go-to downtown, of course, is the 3-mile Freedom Trail. (Go early to beat the crowds!) But for a fantastic destination run, drive or take the commuter rail to Concord to run the Battle Road Trail between Lexington and Concord, and add on an inspiring jaunt over the Old North Bridge (‘shot heard round the world’). 

If you like residential neighborhoods, head just west of downtown for some very nice running in Brookline, Newton, and Wellesley (all on the Marathon route!). Wellesley College, in our view, is one of the Top 10 most beautiful university campuses for running. 

For ‘destination’ runs, we’ve developed guides to Boston’s North and South shores, which feature dozens of gorgeous waterfront routes and historic towns. 

The Marathon Course

The world’s oldest marathon will have its 125th running on October 11, nearly 30 months since the 124th running. Spring blossoms will be replaced by fall colors, with better odds for decent weather, compared to the more fickle and unpredictable Patriot’s Day run in April. In another nod to the traditional 11 a.m. Red Sox game on Marathon Monday, there’s actually a chance that the 2021 Boston Marathon will coincide with a playoff game at Fenway, as Game 4 of the ALDS is scheduled for October 11 should the Sox get that far. 

As for the course, much has been written about the uniqueness of the Boston Marathon — with its early downhill, the Wellesley College ‘tunnel’ at the halfway point, and of course Heartbreak Hill.  One unique aspect of the Boston Marathon course is that it’s the only fully one-way course among the Marathon Majors. Also interesting is the fact the course doesn’t overlap with any of Boston’s three iconic running routes (Charles River, Emerald Necklace, and Waterfront). 

Runners start in the small town of Hopkinton, and first make their way through Ashland, Framingham, and Natick. Mainly downhill, and somewhat blandly pleasant in a tidy, rural New England fashion. But, there’s a very festive, party-like atmosphere on race day. The “Wellesley Tunnel’, at the Marathon’s halfway point, is a highlight for all runners. The next 3-4 miles are through the tony town of Wellesley, then into Newton, where the hills start. The apex of the hills, Heartbreak, is at Boston College near the 21-mile mark, where runners will glimpse the Boston skyline and the iconic Citgo sign. From there, it’s mainly downhill to Cleveland Circle and along Beacon St. through Brookline (fun fact: your Great Runs author lives steps from the 23-mile mark in Washington Square, Brookline). Hit Kenmore Square (Fenway Park, Citgo sign) around Mile 25, and then of course the famous ‘right on Hereford, left on Boylston, to the finish line. 

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About the Author

Mark Lowenstein is Chief Running Officer of Great Runs, the ultimate guide to the best places to run in destinations worldwide. He can be reached at mark.lowenstein@greatruns.com.