The Ultimate Guide to Boston's 21 Neighborhoods

Allston in a nutshell: Picture streets lined with little ethnic shops and restaurants, cheap eats and cheap salons, and the diviest bars in town. Then fill those streets with obnoxious college kids who’ve spent the evening/afternoon filling up in those bars. There you go, you’ve got Allston.

A neighborhood with a few unique historic twists (Boston’s first black school was built here in 1808), the West End is mostly ignored, clumped in with Beacon Hill. But its delights may surprise you yet; after all, this is where the TD Banknorth Garden (and the Celtics and Bruins) lives!

Roxbury is, unfortunately, known to be one of Boston’s toughest neighborhoods. The upside is that she’s also one of Boston’s prettiest. Fresh efforts to clean up and revitalize the neighborhood certainly help.

Hardly a neighborhood of Boston at all (given that it’s not actually subway or trolley-accessible), West Roxbury is nonetheless adorably quaint and a fabulous place to live. Plus, the commuter rail rolls by every 20 minutes or so.

Full of gorgeous parks, ethnic shops, and host to America’s oldest community theatre, Jamaica Plain is simply an awesome place to live.

Founded in 1628, Charlestown sits on the bank of the Charles River and is quite possibly best known for being the site of the Battle of Bunker Hill (and its resultant monument), which was actually held on Breed’s Hill. The neighborhood was nearly voted out of Boston at one time, but fortunately residents let it stick around.

The cobblestone streets and cul-de-sacs of the South End could lead one to believe that they’d fallen into a side street of say, Amsterdam (minus the canals, of course). And yet, the South End (not to be confused with South Boston) is full of world-class restaurants and shopping as well.

Southie is notorious for lots of things: crime, the D Street Projects, Whitey Bulger…But for every ounce of notoriety, there’s a bound of pride – Irish pride, mostly. Another claim to Southie’s fame is the myriad films set or filmed here, including Good Will Hunting, Boondock Saints, Gone, Baby, Gone, The Departed, and Mystic River.

Eastie is isolated, making the rents a bit lower than average, but the view is killer!

As soon as you walk across that bridge, you are no longer in Boston but a main street in some Italian town. Your nostrils fill with the aroma of tomatoes and spices, your eyes search for the coziest restaurant but you can’t decide…that’s the illustrious North End, or as its known in the tourist guides: Boston’s little Italy.

The Kenmore/Fenway neighborhood is what I like to think of as where Boston proper starts and the suburbs begin. Though not entirely (or at all) true, it is in fact where the subway goes above ground, taking Allston/Brighton residents to the surface. And Fenway is famous for one big thing, of course: the Boston Red Sox!

Although Boston’s Chinatown is nowhere near the size of San Francisco’s or New York’s, it’s still a tight-knit community with great places to eat and people-watch.

Back Bay is the neighborhood with everything: a highly commercial area, residential district full of lovely brownstones, and Boston’s highest skyscrapers (namely the Prudential and Hancock buildings). Back Bay is, incidentally, also home to Boston’s version of 5th Avenue: Newbury Street.

Roslindale is an up-and-coming neighborhood nowadays, so snatch up an apartment while you can!