A long-time hub for breweries (even though one theory says the name derives from Jamaica Rum), and once well known for ice harvesting and the manufacture of industrial fans, Jamaica Plain is now a green and culturally diverse enclave for artists, inventive hipsters and commuting professionals. The classic ‘streetcar suburb’—affectionately nicknamed JP—is still aesthetically defined by its 19th century "triple decker" apartments and rewards the curious visitor with a fascinating collection of vintage stores, bars, purveyors of global cuisine and quirky gift shops. JP is also home to the Boston Beer Company, maker of the city’s best-known beer brand: Samuel Adams.
Where to Eat
Japanese/Koren fish hotspot JP Seafood Cafe is well worth a visit for the incredible sushi "boats" and extensive vegetarian maki options—and young sibling, Evergreen Eatery, has also picked up a solid local fan base. Little Dipper is a cosmic diner offering breakfast options themed after the planets (Saturn Stack, Jupiter Stack) and omelets named for orbiting moons. Homely gem Ten Tables is plugged into the regional farming community and has a stellar reputation that extends nationwide.
Where to Shop
Tres Gatos could also appear in the food section, as it serves innovative Spanish tapas and paella, but it’s also a record and bookstore—brain, soul and gut are offered equal satisfaction. Aviary Gallery is another top-notch multipurpose space housing and an artist boutique, photo lab and event space.
Where to Drink
There’s no more iconic watering hole in Boston than Doyle’s Cafe, spiritual home for thirsty politicians and filmmakers (Clint Eastwood et al) on a quest for old-school authenticity. Its location down the road from Boston Beer Company makes Doyle’s a favorite stop for post-Samuel Adams brewery tour revelers, unless they’ve been waylaid in the excellent on-site Sam Adams Tap Room. Brendan Behan Pub pickles the business of boozing in culture and philosophy by laying on literary evenings and live Irish music: some maintain it’s the best Irish bar in Boston.
There’s no shortage of green space in JP, so take to the outdoors at the Arnold Arboretum or the local section of the Emerald Necklace, which extends north-eastwards all the way to Boston Common: Jamaica Pond is a great place to start. The Footlight Club (est. 1877) is America’s oldest community theater, built on the mission to “present the best in non-professional theater to a broad-based audience.” So get your am-dram fix right here. Eclectic music venue The Midway Cafe stays open until 2 am every day of the week, and what’s not to like about that.