Hugged by the Charles River to the south, this primarily residential neighborhood is a picturesque parade of triple-decker homes, children-strewn parks, and the occasional grade school or academic research building. Commerce ranges from the un-ironic industrial (vintage electronics repair), to the vaguely suburban (three major supermarkets), to the charmingly earnest (a tuxedo boutique)—with a soul food shack and a throne-festooned Irish bar thrown in for good effect. And for you snack-history buffs: In the late 1800s the iconic cake-and-fruit Fig Newton cookie was first manufactured here at the F. A. Kennedy Steam Bakery.
Eclectic doesn’t even begin to describe the levels—nay, stratospheres—of communities that overlap in this tiny-but-tenacious patch of the city. Ground zero for live music starts at the intersection of Mass. Ave. and Brookline St. (you can’t miss the lines every night), and the sound bleeds outward from there. Precisely brewed caffeine, Prohibition-inspired cocktails, and high-octane smoothies are always near at hand. Clusters of historic churches commingle with start-up video game offices and brightly lit Indian restaurants. If you pass by at the right time, you can catch a whiff of something sweet—the area’s candy-making history lives on with a bustling Junior Mints facility.
CENTRAL SQUARE IN 90 SECONDS
To be perfectly honest, this neighborhood is probably the most “below the radar” for visitors, but what it lacks in glamour it more than makes up for it in total, earnest hidden-gem-ness. Cruise down its main aorta, Cambridge Street, for access to some of the best fish markets, Portuguese bakeries, and well-loved bars in town. Mallrats can get their fill between the Cambridgeside Galleria and the Twin City Plaza shopping center, but one would be remiss to pass up stylish treasures at the Cambridge Antique Market. The residential makeup is richly diverse, anchored with strong Irish and Portuguese communities. Local pride runs thick.
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Any trip to Cambridge isn’t complete without a proper stroll through storied Harvard Square—it’s too historic, too beautiful, too simply fun to resist. You can walk through the Yard and absorb every inch of ivy-leagued glory on your own, but a proper tour can be ever-more-rich icing on the cake. Bring a knapsack, because you’re never a tweed’s throw away from a bookseller: Grolier Poetry Bookshop, Schoenhof’s Foreign Books, Harvard Book Store (to name but a few). Lest it all seem too cerebral, there are small pleasures aplenty, from crowd-drawing contortionists, to limited runs at the arthouse-iest arthouse theatres, to amazing hot pizza slices to go or cozy, inviting gathering spots to sit for awhile.
HARVARD SQUARE IN FOUR SEASONS
If you have the patience to walk for ten minutes from the nearest subway stop, you don’t have any excuse to pass up this shoo-in winner for “most adorable place, ever.” This highly livable area houses a mix of residents—strong Brazilian and Portuguese communities, plus academics and young professionals—and a smattering of healthy small businesses. Depending on your mood, grab a properly poured Guinness, order a whitefish platter (knish optional), or clutch an aluminum platter piled high with vindaloo. Fashionable secondhand stuff reigns (not to mention good beer), and there’s an experimental gallery on hand for any given ilk.
It's difficult to comprehend how much of the future is created in these parts. Between web behemoths like Google and Microsoft, plus a super-dense cluster of biotech companies, not to mention the festering research going on at Massachusetts Institute of Technology—this is, simply put, a brainy playground for scientific progress. Additionally, architecture fans can geek out on MIT's iconic structures (Frank Gehry's tangle-of-angles Stata Center, Eero Saarinen's sinuous chapel, Fumihiko Maki's see-through Media Lab), while culture nerds can run amok through a fantastic display of contemporary art, crit-theory text, or independent film. Stay for dinner? Kendall's restaurant scene continues to heat up, without any hint of stopping.
As Mass. Ave. unfurls northward from Porter Square, things start to get weird—and wonderful. Strewn along the main drag are some of the funkiest small businesses and authentic ethnic restaurants around. There's a no-nonsense restaurant supply store (fueling every last dinner-party fantasy), a boutique Italian foods retailer, and an Indian bridal showroom. Keep going for more adventures, including a bygone-era steakhouse, a legit donut hut, and a tree-lined bike path leading to Alewife Brook Parkway. If you're willing to stop and smell the flowers, you won't get a better sense of unfettered Cambridge bohemia than this.
Look up! It’s impossible to ignore Gift of the Wind—huge, bright red, and whirling on its own accord—the 46-foot stainless steel kinetic sculpture that anchors this bustling commercial nexus. Crawling with students (Lesley University is headquartered here; Harvard Law School isn't terribly far) and young professionals, Porter is considerably dense with goods and services. They range from the both predictable (coffeeshop, supermarket, gym) to the not-so-much: a lively “Japantown” mall and food court, a sleek vegan shoe boutique, a thronged live music venue that prides itself on no-cover shows. Moreover, Mass. Ave. is a chowhound's playground. Can you spot the organic four-cheese pizza, Ethiopian kitfo-topped injera, or steaming pork-broth ramen?
This sprawling neighborhood isn't so much easily defined by a single persona as it is by its relative preponderance of green land. Between Fresh Pond Reservation (a 155-acre kettle hole lake surrounded by 162 acres of land and a nine-hole golf course), the meditative Charles River Reservation, and bird-watchers' paradise Mount Auburn Cemetery, there's plenty of room to roam. A primarily affluent population dwells among Huron Village (hint: Cambridge resident and chef célèbre Julia Child used to shop here), with quiet luxury lurking in the flower shop, the sandwicherie, the housewares retailer, the mid-century furniture dealer. Not to mention oodles of baby-and puppy-watching, if that's your thing.