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. 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. Often ignored by tourists, the area south of Boston 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 diverse Boston.


1. Arnold Arboretum

prac_info 125 Arborway, Jamaica Plain • 617 524 1718

One of the US’s foremost collections of temperate-zone trees and shrubs covers the peaceful 0.4-sq-mile- (1.1-sq-km-) arboretum. Grouped in scientific fashion, they are a favorite subject for landscape painters, and a popular resource for botanists and gardeners. The world’s most extensive lilac collection blooms from early May through late June, and thousands of Bostonians turn out for Lilac Sunday, in mid-May, to picnic and enjoy the peak of the Syringa blooms. The main flowering period of mountain laurel, azaleas, and other rhododendrons begins around Memorial Day (at the end of May).


Arnold Arboretum

2. Jamaica Pond

prac_info Jamaica Pond Boathouse, Jamaica Way • 617 522 5061 • Open May–Oct: 10am–sunset daily •

This appealing large pond and its surrounding leafy park was landscaped by Frederick Law Olmsted to accentuate its natural glacial features and it offers an enchanting piece of countryside within the city. Locals enjoy the 1.5-mile (2.5-km) bankside path or fish in the 53-ft- (16-m-) deep glacial kettle pond (fishing requires a Massachusetts license – call 617 626 1590). The boathouse rents small sailboats, kayaks, and rowboats in summer.

3. Forest Hills Cemetery

prac_info 95 Forest Hills Ave, Jamaica Plain • 617 524 0128

More than 100,000 graves dot the rolling landscape in this Victorian “garden cemetery,” one of the first of its kind. Maps available at the entrance identify the graves of notable figures, such as poet E. E. Cummings and playwright Eugene O’Neill. Striking memorials include the bas-relief Death Stays the Hand of the Artist by Daniel Chester French, near the main entrance.


Forest Hills Cemetery in Fall

4. Franklin Park

prac_info Franklin Park Rd, Dorchester • 617 265 4084

Frederick Law Olmsted considered Franklin Park the masterpiece of his Emerald Necklace, but his vision of urban wilds has since been modified to more modern uses. The park is home to the second-oldest municipal golf course in the US and the child-friendly Franklin Park Zoo, which contrasts contemporary ecological exhibits with charming zoo architecture, such as a 1913 pagoda-style bird house.


A playground at Franklin Park Zoo

5. 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 was erected in 1634. As New England’s oldest continually fortified site, it is now guarded by Fort Independence (c. 1851). Anglers gather on the adjacent Steel Pier and drop bait into the mass of striped bass and bluefish.


Sandy beach at tranquil Pleasure Bay

6. Centre Street

Jamaica Plain is home to many artists, musicians, and writers as well as a substantial portion of Boston’s gay and lesbian community. Centre Street is the main artery and hub. There is a distinctly Latin-American flavor at the Jackson Square end, where Caribbean music shops and Cuban, Dominican, and Mexican eateries abound. At the 600 block, Centre Street morphs into an urban counter-cultural village, with design boutiques, funky second-hand stores, and small cafés and restaurants.


Centre Street

7. Upham’s Corner

prac_info Strand Theatre, 543 Columbia Rd, Dorchester • 617 635 1403

The area known as Upham’s Corner 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 shops specializing in food, clothing, and the 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.

8. Dudley Square

prac_info Hamill Gallery of Tribal Art, 2164 Washington St, Roxbury • 617 442 8204 • Open noon–6pm Thu–Sat Dillaway-Thomas House, 183 Roxbury St, Roxbury • 617 445 3399 • Call in advance for tour hours

Roxbury’s Dudley Square is the heart of African-American Boston as well as the busiest hub in Boston’s public transportation network. The Beaux Arts station is modeled on the great train stations of Europe. Among the square’s many shops and galleries is the Hamill Gallery of Tribal Art, as much a small museum as a gallery. A few blocks from the square, the modest Georgian-style Dillaway-Thomas House reveals Roxbury’s early history, including the period when it served as HQ for the Continental Army’s General John Thomas during the Siege of Boston.

9. Edward M. Kennedy Institute for the United States Senate

prac_info 210 Morrissey Blvd, Dorchester • 617 740 7000 • 10am–5pm Tue–Sun • Adm •

Displaying re-creations of the US Senate Chamber and Senator Edward M. Kennedy’s office, this facility provides an impressive interactive experience of how the Senate functions. With film and live actors, ‘Great Senate Debates’ recreates historic turning points in the Senate.

10. John F. Kennedy Library and Museum

prac_info Columbia Point, Dorchester • 617 514 1600 • Open 9am–5pm daily • Adm •

This nine-story pyramidal building designed by I. M. Pei in 1977 stands like a billowing sail on Columbia Point. Inside, exhibits recount the 1,000 days of the Kennedy presidency. Kennedy was the first president to grasp the power of broadcast, and video exhibits include campaign debates, as well as coverage of his assassination and funeral.


John F. Kennedy Library and Museum




The Orange Line “T” delivers you to the Latin end of Jamaica Plain’s Centre Street at Jackson Square, where life is more Santo Domingo than “Downtown Boston”. Head west and ease into the rhythm by sampling empanadas, coffee, and Latin desserts at Gondres Bakery (333 Centre St). A walk along Centre Street serves up a cornucopia of Latino fashion and specialty shops. Del Valle’s Children’s Gift Shop (360 Centre St) has clothing from christening gowns and rompers to dress shoes and jewelry. Follow Centre Street as it doglegs left. Hip Streetcar (488 Centre Street) carries a large selection of boutique wines and craft beers. At J P Licks (659 Centre St) order a cone of super-premium ice cream, and continue to Boing! JP’s Toy Shop (667 Centre St) to discover fun gifts for kids from one to 91. Jeweler Phil Celeste carries unique clothing, jewelry and gift items at On Centre (676 Centre St), while Fire Opal (683 Centre St) showcases handmade American art, apparel, and jewelry. The thrift store Boomerangs (716 Centre St) has clothing and home decor. Stroll up Burroughs Street and cross Jamaicaway to Jamaica Pond to stroll, sit in the shade, or rent a rowboat.


Once you’ve worked up an appetite, return to Centre Street for dinner at Vee Vee. Afterward, hit ultra-hip Milky Way Lounge for a chilled beer, live music, and dancing.

Bars and Clubs

1. The Jeannie Johnston

prac_info 144 South St, Jamaica Plain

This entertainment venue has plenty to offer, with an open mic on Thursdays, live local bands on Fridays, and karaoke on Saturdays, as well as a snug spot to sit with one of its 35 draft or bottled beers.

2. Milky Way Lounge

prac_info 284 Amory St, Jamaica Plain

Situated in JP’s legendary Brewery Complex, Latinos and Jamaica Plain hipsters rub shoulders at the Milky Way. They come for the dancing, the latest local live bands, and the exceptional cosmopolitans.

3. The Punk & Poet

prac_info 658 East Broadway, South Boston

Stylish Irish punk pub serving good bar-friendly food (including burgers, wings and fish and chips) and a range of local and non-local beers.

4. dbar

prac_info 1236 Dorchester Ave, Dorchester

The eclectic dinner menu disappears around 10pm, when dbar morphs into a hopping, diverse nightclub where brightly colored cocktails are a specialty. Show tunes on Tuesdays, karaoke on Fridays.

5. Lucky’s Lounge

prac_info 355 Congress St, South Boston

A Fort Point Channel underground bar that swaggers with rat-pack retro ambience, right down to the lounge acts and the unmissable Frank Sinatra tribute nights.

6. The Broadway

prac_info 734 East Broadway, South Boston

On weekends this watering hole is packed both inside and outside in the garden. Modern pub food hits a fairly high mark.

7. L Street Tavern

prac_info 658A East 8th St, South Boston

One of Southie’s most old-fashioned pubs, L Street serves Harpoon and Guinness on tap. The Oscar-winning movie Good Will Hunting was filmed here.

8. Brendan Behan Pub

prac_info 378 Centre St, Jamaica Plain

This Irish pub is frequented by neighborhood types with vaguely poetic pretensions, and outfitted with Guinness and Murphy’s on tap. Live music most nights.

9. Local 149

prac_info 149 P St, South Boston

This South Boston neighborhood joint features local beers on tap, creative cocktails, and some of the best New American food outside of a fancy restaurant.

10. Doyle’s Café

prac_info 3484 Washington St, Jamaica Plain

The apex of Irish-American political culture, Doyle’s has been serving beer since 1882, and corned beef and cabbage on Thursdays for as long as anyone can remember.


Bar at Doyle’s Café


1. Coppersmith

prac_info 40 W 3rd St, South Boston • 617 658 3452 • $$

This vast converted warehouse has an American bistro restaurant as well as a casual café serving global fare. Try the BBQ popcorn, which is excellent.

2. Tres Gatos

prac_info 470 Centre St, Jamaica Plain • 617 477 4851 • $

This combination tapas bar and book/music store features authentic Spanish bar dishes along with some inventive variants.


Bright decor at Tres Gatos

3. Yellowdoor Taqueria

prac_info 2297 Dorchester Ave • 857 267 4201 • Closed L • $

This snazzy Mexican bar in Lower Mills specializes in craft cocktails, rare tequila, and local beer. Food includes innovative tacos, healthy salads, and great ceviches.

4. Ashmont Grill

prac_info 555 Talbot Ave, Dorchester • 617 825 4300 • Open daily for D and L Fri, brunch Sat & Sun • $$

Veteran chef Chris Douglass uses local produce to conjure up contemporary bistro delights.

5. El Miami Restaurant

prac_info 381 Centre St, Jamaica Plain • 617 522 4644 • $

This place is the self-proclaimed “King of the Cuban sandwiches.” Check out the photos of the Latino pro baseball players who often eat here when in town.

6. Tavolo

prac_info 1918 Dorchester Ave, Dorchester • 617 822 1918 • Closed L • $$

Superb, rustic Italian cuisine emphasizes fresh market dining in this Ashmont neighborhood.

7. Ten Tables

prac_info 597 Centre St, Jamaica Plain • 617 524 8810 • Closed L • $$$

This small venue has just ten tables with, an equally compact but rewarding menu, such as scallops on minted pea tendrils.

8. Vee Vee

prac_info 763 Centre St, Jamaica Plain • 617 522 0145 • Closed L and Mon • $$

Delectable American bistro fare makes this restaurant a favorite with local foodies, especially since many dishes have vegetarian versions. The Sunday brunch is very popular.

9. Bella Luna

prac_info 280 Armory St, Jamaica Plain • 617 524 6060 • $$

The dining room adjacent to the Milky Way Lounge, Bella Luna shoots the moon with bright salads, rib-sticking Italian fare such as chicken marsala, and their signature gourmet pizzas.

10. Blue Nile

prac_info 389 Centre St, Jamaica Plain • 617 522 6453 • Closed Mon • $

Ethiopian home-style food celebrates fresh vegetables as well as meats and fish, and there’s plenty of choice for vegans as well. Teff injera, the sourdough pancakes that double as utensils, are made on the premises.

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