• Kingfish Hall Restaurateur Todd English sinks his culinary hooks into zesty fish dishes just a few blocks away from the farmers’ market at City Hall Plaza.
  188 S. Market, Faneuil Hall Marketplace;
  617-523-8862.
• Union Oyster House Billed as America’s oldest restaurant, this well-known spot has sold New England seafood since 1826. Bartenders serve up freshly shucked oysters at a U-shaped bar. Pair a bowl of “chowdah” and warm corn bread with a mug of Harpoon IPA.
  41 Union St.; 617-227-2750.
• Mantra Serving French cuisine with Indian accents, this cosmopolitan spot offers inventive dishes such as cumin-dusted duck breast with baby bok choy.
  52 Temple Place; 617-542-8111.
• Finale Desserterie Save room for this sweet after-dinner stop, a plush dessert café with candlelight and offerings like molten chocolate cake. The popular place was inspired by a field study by a trio of Harvard Business School students. 1 Columbus Ave.; 617-423-3184.
• Veggie Planet Harvard students love the wholewheat pizza with squash and goat cheese at this Cambridge pizzeria. 47 Palmer St.; 617-661-1513.

• Ars Libri Ltd. This quiet shop stocks rare and out of print books on the fine arts.
  500 Harrison Ave.; 617-357-5212.
• Fort Point Arts Community Gallery On the ground floor of the historic Artist Building in the reviving Seaport District, this gallery both displays and sells local artists’ works.
  300 Summer St.; 617-423-4299.
• Wish Women’s fashions from the likes of Trina Turk, Tibi, and Milly line the racks of this boutique.
  49 Charles St.; 617-227-4441.
• Brattle Book Shop This three-story treasure trove is filled with rare and used books for sale.
  9 West St.; 617-542-0210.
• Stephen Score Antiques Among the many antiques shops on and around Charles Street, this spot is known for its folk art.
  73 Chestnut St.; 617-227-9192.
• Barbara Krakow Gallery Contemporary art from artists like Sol Le- Witt and Jenny Holzer grace the walls at this significant art spot.
  10 Newbury St.; 617-262-4490.
• Polcari’s Coffee A real old-world shop in the North End selling more than 30 varieties of coffee beans, bulk teas, and 160 spices.
  105 Salem St.; 617-227-0786.

Bostonians distinguish Cambridge from the rest of town by calling it “The People’s Republic of Cambridge.” And though the MIT-Harvard juggernaut still dominates, the end of rent control in the 1990s saw an exodus of left-leaning types and an influx of market forces.

Still, Harvard Square has not been swept clean by the broom of gentrification. Fill up first at Mr. Bartley’s, which still serves burgers named after politicians and sports heroes. Soak up highbrow culture with plays at the American Repertory Theater, movies at the Harvard Film Archive and the Brattle Theatre, readings at the Harvard Book Store, and great art at the Arthur M. Sackler Museum.

West of Harvard, amble down Brattle Street’s Tory Row, where brick sidewalks front historic mansions like the Longfellow House, gathering place for 19th-century writers like Emerson and Hawthorne. End your tour in Central Square, home of the area’s best nightlife— from old-school Irish pub Plough & Stars to sleek drink spot Middlesex Lounge to live music hub Middle East.

• 21st Amendment At this cozy pub across from the State House, state reps and senators mingle with law students. Order a Sam Adams and a cheeseburger.
  150 Bowdoin St.; 617-227-7100.
• Green Dragon Tavern Throw back a few cold ones where the “Sons of Liberty”—Sam Adams, Daniel Webster, and Paul Revere—planned the Boston Tea Party.
  11 Marshall St.; 617-367-0055.
• Club Passim Joan Baez got her start here. A great place to see top acoustic musicians play in an intimate setting.
  47 Palmer St., Cambridge; 617-492-7679.
• Matt Murphy’s Waiters at this popular pub hail from the U.K. Pints of ale, rabbit pie, beef stew, and fish-and- chips served in newspaper just add to the ambiance.
  14 Harvard St., Brookline Village;
  617-232-0188.
• Black Rose Soak up Beantown’s Gaelic heritage with a pint of Guinness and live Irish music nightly at one of the town’s premier Irish pubs, open since 1976. The made-from-scratch clam chowder reminds you that you’re in New England.
  160 State St.; 617-742-2286.