SOUTH OF BOSTON
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 edgy, diverse Boston.
1.Arnold Arboretum
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
Jamaica Pond Boathouse, Jamaica Way • 617 522 5061 • Open mid-Apr–Oct: noon–sunset Mon, Wed, & Thu (from 10am Fri–Sun) • www.cityofboston.gov/parks 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 take avidly to 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.
Jamaica Pond
3.Forest Hills Cemetery
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
Forest Hills Cemetery
4.Franklin Park
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 Oriental bird house.
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’s now guarded by Fort Independence (c. 1851). Anglers gather on the adjacent Steel Pier and drop bait into the midst of striped bass and bluefish runs.
Sandy beach at tranquil Pleasure Bay
6.Centre Street
Jamaica Plain is home to many artists, musicians, and writers as well as a substantial contingent 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
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
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
210 Morrissey Blvd, Dorchester • 617 740 7000 • Open 9am–5pm Tue–Sat, 10am–5pm Sun • Adm • www.emkinstitute.org 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. The ‘People Who Made a Difference’ exhibit highlights citizens who made an impact on civic life.
10.John F. Kennedy Library and Museum
Columbia Point, Dorchester • 617 514 1600 • Open 9am–5pm daily • Adm • www.jfklibrary.org 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
STREET HEAT & POND COOL IN JAMAICA PLAIN
Afternoon
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.
Evening
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
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 27 draught or bottled beers.
2.Milky Way Lounge
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.Playwright Bar
658 East Broadway, South Boston A spiffy Dublin-style pub with good food, excellent pints, and large windows that let in the sunlight and the breeze.
4.Dbar
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, rock videos on Fridays.
5.Lucky’s Lounge
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.Boston Beer Garden
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.Amrheins
80 West Broadway, South Boston The vintage bar at Amrheins – a South Boston fixture since 1890 – is reason enough to visit the ‘hood. Locals debate the issue of the day over a drink or two.
8.Brendan Behan Pub
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
149 P St, South Boston This South Boston neighborhood joint features 22 beers on tap, plus innumerable cans and bottles, and some of the best New American food outside of a fancy restaurant.
10.Doyle’s Café
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. Busy nightly.
Doyle’s Café
Restaurants
1.Coppersmith
40 W 3rd St, South Boston • 617 658 3452 • Closed Mon and L Tue–Fri • $$ This vast converted warehouse has an American bistro restaurant as well as two food trucks serving global fare. Try the BBQ popcorn.
2.Tres Gatos
470 Centre St, Jamaica Plain • 617 477 4851 • $ This combination tapas bar and book/music store features authentic Spanish bar dishes along with some inventive variants.
Tres Gatos
3.224 Boston Street
224 Boston St, Dorchester • 617 265 1217 • Closed L • $ This chef-driven northern Italian trattoria is the longest lasting and most successful restaurant in the ‘hood. Enjoy a Tuscan feast for half the price of North End’s restaurants.
4.Ashmont Grill
555 Talbot Ave, Dorchester • 617 825 4300 • Open daily for D and L Mon–Fri, brunch Sat & Sun • $$ Veteran chef Chris Douglass uses local produce to conjure up contemporary bistro delights.
5.El Miami Restaurant
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
1918 Dorchester Ave, Dorchester • 617 822 1918 • Closed L • $ Superb, rustic Italian cuisine emphasizes fresh market dining in this Ashmont neighborhood.
7.Ten Tables
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
763 Centre St, Jamaica Plain • 617 522 0145 • Closed L and Mon • $$ Delectable American bistro fare makes this 35-seat restaurant a favorite with local foodies, especially since many dishes have vegetarian versions. The Sunday brunch is very popular.
9.Bella Luna
280 Armory St, Jamaica Plain • 617 524 6060 • $$ 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
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.