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Boston is a city with one foot in the past and one in the future. Known for being the cradle of the American Revolution and home to countless locales that will entrance history buffs, it’s also a hotspot for innovation thanks to the many universities that call this city home. Boston’s neighborhoods shine for reasons beyond the Freedom Trail and Harvard Yard, however; so, sample what each one has to offer, from tourist staples to local favorites.
Downtown Boston is a collision of present and past. Here, you can follow in the footsteps of Revolutionary War heroes as you navigate through skyscrapers. Outside the Old State House, find the plaque that commemorates the Boston Massacre before walking the rest of the Freedom Trail—just follow the red brick installed in the sidewalk that shows the route. Alternatively, take a tour of the Boston Tea Party ships.
Then, enjoy dinner at the decidedly modern No. 9 Park, led by acclaimed Boston chef Barbara Lynch. If you have extra time to spare, check out the nearby neighborhoods of Beacon Hill or Chinatown—both worthy stops in their own right.
Built in the 19th century on land reclaimed from the Charles River, the Back Bay was—and continues to be—where the swankiest of Boston live, work, and play. The center of the neighborhood is Copley Square, where the beautiful Trinity Church stands in the reflection of the blue-glass John Hancock Tower. Just steps away, Newbury Street houses designer clothing stores and upscale cafés and is perfect for an afternoon stroll.
Steeped in Italian culture and history, the North End is a must-visit for food and history. The biggest debate in town is whether Mike’s Pastry or Modern Pastry sells the best cannoli. The only way to know for sure is to try both—but don’t forget the pizza, either.
The North End is also home to the Old North Church, where two lanterns were hung to let the watching Paul Revere know that the British were coming by sea instead of by land. More recently, the neighborhood has been revitalized thanks to the work of the Big Dig, which resulted in the beautiful North End–bordering Rose Kennedy Greenway.
Charlestown is one of the oldest Boston neighborhoods and remains mostly residential, with notable architecture and history. Start at the Bunker Hill Monument, which commemorates one of the first battles of the Revolutionary War (and actually sits atop Breed’s Hill, not Bunker). The colonists lost that day, but the heroism of the small band against the much stronger British army helped cement public support for the cause.
Then, walk through the old streets and have a drink at the Warren Tavern, which is the oldest bar in Massachusetts—open since 1780!—and was frequented by Ben Franklin and George Washington. You can also check out Bunker Hill Community College, where the classic movie Good Will Hunting was set.
This neighborhood just west of Back Bay is home to some of Boston’s flagship institutions, from major hospitals to Fenway Park to renowned museums. Baseball is in Boston’s blood, and so there’s no escaping the necessity to don a cap and visit the oldest MLB ballpark—you could even tour the park before the game.
Nearby, the impressive collection at the Isabella Stewart Gardner Museum—modeled on a Venetian palazzo—is another highlight, which saw one of the largest art heists in history back In 1990. The places on the wall where the paintings once hung are still left blank, in the hope that one day the works will be recovered.
Only 10 years ago, the Seaport District was little more than parking lots and one underused concert venue. Today, it’s one of the most exciting places in Boston for shopping, eating, and drinking. Here, you’ll also find the internationally-renowned Institute of Contemporary Art, which cycles its exhibitions every few months and which recently opened a satellite venue, accessible by free ferry ride, in East Boston. Not one for dry land? Opt for a sailboat tour around nearby Boston Harbor.
Dorchester and Roxbury are large neighborhoods south of downtown, easily accessible by public transit and home to diverse populations and long histories. In Roxbury, visit the museum of the National Center of Afro-American Artists and then take a walk at the Arnold Arboretum, a massive green space owned by Harvard University with over 14,000 trees from across the world.
In Dorchester, visit the John F. Kennedy Presidential Library and Museum near the Harbor, then check out the recently-designated Boston Little Saigon Cultural District for the best Vietnamese food in New England.
One of the most diverse parts of Boston, travel to “Eastie” for a taste of the best of the many communities that call this city home. Here, try tamales at Taquería Jalisco, pho at Saigon Hut, and arepas at El Peñol while hearing dozens of languages spoken around you. The entire neighborhood lies next to the busy Logan Airport, but the many parks and skyline views make up for the noise. East Boston is far from the tourist route, but it’s well worth the trip.
So, Cambridge is not a Boston neighborhood—it’s a city with a unique history and vibe unto itself. However, a quick ride on the Red Line of the T will bring you across the Longfellow Bridge and into this famous burg, where some of the world’s brightest minds design world-class biotechnology, browse the stacks in Harvard’s Widener Library, and catch movies at the arthouse Brattle Theater.
Flanked by Harvard and MIT, Cambridge is made up of numerous “squares,” from Kendall to Central to Inman. After enjoying the cafés, bookstores, and art museums, be sure to catch a tour of those storied universities—maybe a diploma is in your future?