Runners Guide to Boston for the Boston Marathon

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 for running, with its setting on the Charles River and Atlantic Ocean, and pedestrian-scale historic neighborhoods. 

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

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

Charles River Paths. One of the 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, which runs past Harvard and MIT and features the best views of the river and the Boston skyline. A signature ~10 mile loop is from the Museum of Science to the JFK Bridge (Harvard University). The heart of the paths do get cleared of snow in winter. 

The Emerald Necklace. A greenway originally conceived by Frederick Law Olmsted, running 10 miles from the State House to Franklin Park. Highlights 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. This one 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. Great water views the whole way. Part of the Harborwalk.

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, Necklace, and historic neighborhoods make all the ‘best of Boston running’ lists, there are also some hidden gems that are worth the extra effort. 

Take the Blue Line to the Airport station to enjoy a fantastic run in East Boston, which has a wonderful running path and killer skyline views. One of the nicest 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 5 miles of dirt trails over rolling hills, with great views of the water and the Boston skyline.

There’s also some great running for history buffs. 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 with 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 & South shores, which feature dozens of gorgeous waterfront routes and historic towns. 

The Marathon Course

The Boston Marathon is always the third Monday in April — the Patriot’s Day holiday in Massachusetts. There’s a ceremony in Lexington and Concord, the blossoms are out, and there’s a traditional 11am Red Sox game on Marathon Monday. Also note that April weather is notoriously fickle — it’s never actually ‘average’! If the wind is blowing from the east (off the water), it will be cool, and possibly very raw. If it’s blowing from the west, it will be warm. And it can change quickly. 

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 about the Boston Marathon course is that it’s the only fully one-way course among the Marathon Majors. Another 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 make their way through Ashland, Framingham, and Natick. Mainly downhill, and not that scenic. But, there’s a very festive, party-like atmosphere. The “Wellesley Tunnel’, at the Marathon’s half-way 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 at Mile 18 after the right turn onto Commonwealth Ave. at the fire station. The apex of the hills 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. Incidentally, there’s a Marathon Sports location directly across the street — probably the best- situated running store in the world.