Boston's Wonderful Walking Trails

Get out and explore America's Walking City

Boston owns a whole bunch of nicknames, some more popular than others—from the braggadocio Hub of the Universe to the locally unloved Beantown—but a consensus of approval clings to our favorite: America’s Walking City. There’s nothing that a curious mind and a stout pair of sneakers can’t discover on both sides of the Charles River, and any given route offers a surplus of watering holes and eateries, should you need to stop and recharge your batteries.


The most famous walking route through the city is The Freedom Trail, dedicated in 1951. The easy-to-follow 2.5-mile red line connects a series of historic sites and national treasures, including Faneuil Hall and The Paul Revere House. You can either arrange your own city ramble from the Common to Bunker Hill via the North End and Charlestown Bridge, or take advantage of the many guided tours offered by Freedom Trail experts who dress up in historically authentic outfits. A side expedition through Beacon Hill along the Black Heritage Trail is highly recommended.


The Common itself, and its beautifully cultivated neighbor, the Public Garden, should also be visited any day the sun has got his hat on. The Swan Boats on the Public Garden lagoon have been gliding serenely through idle summer days since 1877, and make a great change of pace, while the Frog Pond—defrosted from its winter duty as an ice rink—is the ideal spot to ease tired feet while the kids give themselves a thorough soaking. The Common also marks the eastern end of the Emerald Necklace park system: Check out the map to see its full extent, all the way to Franklin Park.


Looping round the Financial District from Chinatown to the North End, following the ghost of the now demolished elevated roadway, is The Greenway. More than just a modern city park, this marvelous strolling zone is a wonderland of craft beer pop-ups, amazing public art and special events, from Greenway Gala to Glow in the Park.


If you fancy a side of retail therapy with your sidewalk odyssey, be sure your route takes in the full length of Newbury Street, where global brands share a parade of gorgeous 19th-century brownstones with world-class restaurants, walk-up art galleries and basement boutiques. From here, it’s an easy stroll towards the river, where you can pick up The Esplanade, a 3-mile waterfront park on the Boston side of the Charles, via several footbridges over Storrow Drive.


A brisk walk across one of the major river bridges will deliver you to Cambridge and Somerville, home of some of the best local walking tours. One of our favorites is Off the Beaten Path Food Tours, which sheds a delicious new light on Union Square and Davis Square with the Food & Marshmallow Fluff Tour. If you run out of steam, head for the nearest Red Line stop for a T train back across the water.


Mike Hodgkinson
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