Guided Tour: Jamaica Plain

378 Centre St, Jamaica Plain, MA 02130 (map)

Deliciously dark and of diminutive size, the Behan's a local favorite for perfectly poured pints, impromptu live Irish music sessions and instant mesmerization via the large fish tank. Rounds of stouts amidst the intimate warmth make for a natural, go-to watering hole at this end of Centre Street.

435 S Huntington Ave, Jamaica Plain, MA 02130 (map)

The tight-knit neighborhood might have been initially miffed when their dependable dive Triple D's was transformed into a cocktail lounge, but soon all was forgiven thanks to the excellent drinks (employing soy milk when appropriate for the vegans, natch) and a laid-back vibe harnessing a refreshing bit of grit. No cover, live DJs and weekend brunch create a loyalty of Alchemist's own deserving.

659 Centre St, Jamaica Plain, MA 02130 (map)

This sprawling local chain for rich homemade ice-cream (in spunky flavors like Cherry Ortiz and Kowlua), freshly roasted coffee and cow-pun decor galore proudly established its flagship on Centre Street. You can't miss it, from the enormous bovine head on the facade to the hordes of lingering, cone-licking customers within.

416 Centre St, Jamaica Plain, MA 02130 (map)

One of the many upsides of JP's extant Cuban community is that you (or at least your stomach) can virtually escape to Havana at El Oriental. Prepare for generous portions (at small prices) of craveable Latin comforts like ropa vieja, crunchy tostones and a killer, achingly authentic Cuban sandwich.

3346 Washington St, Jamaica Plain, MA 02130 (map)

Admittedly, there's not much on this side of the railroad tracks for the typical outsider, but it'd be shame to overlook one of the best bakeries in the city. Canto 6, locally owned and operated, produces a drool-inducing array of rustic European pastry every day. Just follow your nose to the cinnamon-laced sweet rolls, chocolate-cherry cookies and blue-cheesy ham biscuits.

597 Centre St, Jamaica Plain, MA 02130 (map)

Passionate foodies flock from all corners of the city to seek a seat among this tiny restaurant's, yes, 10 tables. With a reputation that belies its size, the kitchen produces lovely plates featuring local and seasonal fare at absurd-for-this-quality prices. For a total steal, make an ambitious reservation for its weekly vegetarian or prix-fixe specials.

40 South St, Jamaica Plain, MA 02130 (map)

Jamaica Plains is home to plenty of top-notch vintage clothiers, but 40 South Street remains one of the major pioneers of the secondhand sartorial study. Formerly Gumshoe, a gleaming hidden gem for menswear, the renewed space specializes in handpicked, madly styled pieces for both sexes. The owners will ensure you look smashing.

385 Centre St, Jamaica Plain, MA 02130 (map)

Stick it to the man by eschewing corporate video stores, opting instead for the lovably off-kilter selections at the Video Underground. Racks of independent, cult, alternative, foreign, adult and locally made films are available for rent or purchase, with plenty of passionate staffers ready to recommend an obscure title.