DK Travel : Boston : Boston South

South of Fort Point Channel, Boston’s neighborhoods of Jamaica Plain, Roxbury, Dorchester, and South Boston are a mixture of densely residential streets and leafy parklands that form part of Frederick Law Olmsted’s Emerald Necklace (see Boston Common & Public Garden). The lively street scenes of Boston’s African-American, Latin American, and Irish-American communities make the city’s southerly neighborhoods a dynamic ethnic contrast to the more homogenized city core. Virtually ignored by tourists, Boston South is full of quirky shops, local bars, hot nightclubs, and great off-beat places to enjoy ethnic food. This area is a little harder to reach but it is worth the effort to experience a more edgy, diverse Boston that many call home.

Note: For the parks and cemetery take the “T” down to Green Street or Forest Hills (orange line) Note: Parks and cemeteries are generally open from dawn to dusk Note: Take the “T” to Dudley Square for Roxbury (silver line), or to Jackson Square for Jamaica Plain (orange line) Note: For the John F. Kennedy Library and the east of the area catch the “T” to JFK/U Mass (red line)

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John F. Kennedy Library & Museum

This nine-story white pyramidal building designed by I. M. Pei in 1977 stands like a billowing sail on Columbia Point, as inspiring as the president it memorializes. Inside, the 1,000 days of the Kennedy presidency are recreated in more than 25 exhibits. Kennedy was the first president to grasp the power of broadcast, and video exhibits include campaign debates and coverage of Kennedy’s assassination and funeral.
Lucky’s Lounge

A Fort Point Channel underground bar that swaggers with rat pack retro ambience, right down to the lounge acts and the Frank Sinatra tribute nights.
Milky Way Lounge & Lanes

Latinos and Jamaica Plain hipsters rub shoulders at the Milky Way for the dancing, the latest local live bands, the cosmopolitans, and bowling under the dim blue Christmas lights.
Playwright Bar

A spiffy Dublin-style pub with good food, excellent pints, and large windows that let in the sunlight and the breeze.
Pleasure Bay

South Boston’s Pleasure Bay park encloses a pond-like cove of Boston harbor with a causeway boardwalk, where locals turn out for their daily constitutionals. Castle Island, now attached to the mainland, has guarded the mouth of Boston harbor since the first fortress, Fort Independence, was erected in 1779. A grisly murder here in 1817 inspired Edgar Allen Poe to write his short story The Cask of Amontillado . Anglers gather on the adjacent Steel Pier and drop bait into the midst of striped bass and bluefish runs.
Samuel Adams Brewery

With its supply of good local water and German immigrants, Jamaica Plain has long been Boston’s brewing center. The Boston Beer Company, creator of Samuel Adams lagers, maintains this small brewery and a tongue-in-cheek beer museum.
Slades Bar & Grill

Generous drinks, good jazz, and sometimes even free eats ensure Slades hops on the weekends. Don’t let the seedy exterior put you off – this is one of Roxbury’s liveliest social scenes.
Tacos el Charro

This is the best place in town for real northern Mexican food, plus it has the most complete line of Mexican beers in town. The owner plays in a mariachi band at weekends.
Upham’s Corner

The area known as Upham’s Corner in Dorchester was founded in 1630, and its venerable Old Dorchester Burial Ground contains ethereal carved stones from this Puritan era. Today, Upham’s Corner is decidedly more Caribbean than Puritan, with small shops specializing in food, clothing, and music of the islands. The Strand Theatre, a 1918 luxury movie palace and vaudeville hall, functions as an arts center and venue for live concerts and religious revival meetings.
Woody’s L Street Tavern

This classic Southie dive immortalized in the film Good Will Hunting has gained a certain fame from the movie but retains its insular South Boston crustiness and ultra-conservative political viewpoint.

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Restaurant price categories

For a three course meal for one with half a bottle of wine (or equivalent meal), taxes, and extra charges.
- under $30
- $30–$45
- $45–$60
- $60–$75
- over $75