Jamaica Plain Guide

Learn the ropes with our Jamaica Plain guide--JP remains one of the most fascinating intersections of diversity in Boston. The progressive neighborhood attracts artists, grad students and political activists alike, as well as a supportive gay-lesbian community. It's also home to a large number of Cuban, Dominican and Puerto Rican immigrants. Which, altogether, creates a haven for unparalleled eats, one-of-a-kind businesses and a happy, colorful populace. Dig in.



(Photo: Courtesy of Canto 6)

Updated: June 29, 2010

Jamaica Plain Guide


J.P. Licks

659 Centre St, Jamaica Plain, MA 02130

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.


El Oriental de Cuba

416 Centre St, Jamaica Plain, MA 02130

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.


Brendan Behan Pub

378 Centre St, Jamaica Plain, MA 02130

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.


Ten Tables

597 Centre St, Jamaica Plain, MA 02130

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.

40 South St, Jamaica Plain, MA 02130

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.


City Feed & Supply

66 Boylston St, Jamaica Plain, MA 02130

A stalwart of the burgeoning, hippie 2.0, progressive culture of Jamaica Plains, City Feed & Supply caters to hungers of all ilk with natural foods, fair-trade coffee and a selection of signature sandwiches chock full of free-range this and locally made that. Two central locations keep all fed, happy and conscientious.


The Video Underground

385 Centre St, Jamaica Plain, MA 02130

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.


Canto 6 Bakery & Cafe

3346 Washington St, Jamaica Plain, MA 02130

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.