Boston: Hoofing It in Beantown

Pack your sneakers. Boston is not a city to peer at through a tour bus window. It’s one of the most compact arenas of eye candy the country offers—a town that demands you walk the walk as well as hear the talk. Never mind: You can’t fathom the “beeh and pizzur” accent anyway.

Start in right where our nation got its start: the two-plus-mile Freedom Trail, outlined in red brick, that leads you from one OMG moment to another—the first this, the oldest that—along with the jaw-dropping You Are There experience of standing right where history was made.

Harvard University and Charles River, Cambridge; British “Red Coats” at Harborfest and Patriots Day; Massachusetts State House. Photos Courtesy of Greater Boston Convention & Visitors Bureau

The trail starts at the Boston Common, America’s first (1625) public park, today the realm of winter skaters and summer Swan Boat riders on Frog Pond, amid parolees from office asylums enjoying a lunch break where cattle once grazed.

Alongside stands the golden-domed Massachusetts State House of 1798, with its red-brick exterior, more cozy than ornate. Historic churches also seem proto-Bostonian in their puritanical banishment of ostentation. Yet, within these meetinghouses, inflammatory oratory incited the Tea Party and later antislavery crusades. Beside them, graveyard headstones are inscribed with names like Sam Adams, Ben Franklin, John Hancock, and Paul Revere, along with lesser monuments whose skull-and-crossbones serve as a heads-up to passing sinners.

See the Old State House of 1712. From its balcony, the Declaration of Independence was read. Patriots gathered at nearby Faneuil Hall, AKA the Cradle of Liberty, to lambaste the British, where today’s merchants, in its reincarnation as a Festival Marketplace, gladly take a contemporary UK visitor’s money.

Next, the trail leads past the Union Oyster House (1826)—oldest restaurant in the country—where in a previous incarnation as Capen’s Dry Good Store, General George Washington recompensed his troops on payday. Stop for a bowl of “chowdah” in the booth favored by President John Kennedy.

Then, trudge to the house of Paul Revere, from 1680—oldest in Downtown Boston—and Old North Church of “two if by sea” fame. Finally, cross the river to where Old Ironsides floats—oldest warship in the world—and the monument to the Battle of Bunker Hill (“Don’t fire until you see the whites of their eyes”).

Rainbow banners dressed many a church on the day gay marriage was made legal. Blacks long have considered Boston a place of sane refuge—another walking trail through Beacon Hill leads to America’s first African-American church and public school (separate but “equal”), refuge from slave hunters. A statue in the Commons commemorates the state’s black military brigade in the Civil War.

Beacon Hill is a grand place to begin our stroll through Boston’s distinct and delightful neighborhoods. Its prim brick townhouses, with gas lampposts and original windows of wavering glass, are home to the politically conscious elite who patrol the boutiques and cafés of Charles Street, stopping for peace-grown coffee and artisan bread. Even a Ye Olde 7-Eleven is disguised with vintage brick.

The city’s jail has been airbrushed into a fancy hotel called The Liberty, where celebs stay and dine at (ahem) Clink on veal-ricotta meatball sliders; smoked bay scallops livened with blood oranges; and Berkshire pork loin paired with grits and collard greens. The original Cheers bar is close by, abhorred by locals—you’ll spot it by the busy cameras of visiting Japanese.

At the end of the Commons stand the Brahmin mansions of Back Bay. The showcase artery is Newbury Street, making New York’s Fifth Avenue look downright tacky, thanks to scads of boutiques that haven’t got wind of the recession—a Filene’s Basement somehow defied the zoning code. Hotels such as The Fairmont, Mandarin-Oriental, and Colonnade excel in cosseting your Inner Monarch, hosting restaurants to pamper the most avant palate: Oak Room, where Versailles meets steakhouse; l’Espalier, the St. Peter’s of fine dining; and Brasserie Jo, fun French fare.

Giving those graybeards a run for our money is the brand-new W Hotel in the theater district, housing Market, an outpost of culinary pontiff Jean Georges, who pulled his lead chef, Chris Damskey, from the former Chambers Kitchen in Minneapolis to head the line here. It stars reinvented regional fare such as black pepper crab fritters with Asian pears and endive; rice cracker-crusted tuna bathed in citrus-chili oil; fabulous foie gras brûlée balanced by pineapple-Meyer lemon jam; and divine local haddock in mint and fragrant coconut juice—or (gulp!) pizza topped with clams and chilis.

Head back in history to the Langham Hotel, born of a 1920s bank, now home to Bond, a renaissance of the space’s domed vault, where see-and-be-seeners flock to sip their Sawbucks martinis (Grey Goose, lime, and ginger), while demolishing small plates, such as smoked-salmon pierogi; fried Brussels sprouts with pork belly; or lobster-chanterelle pot pie, followed by way-too-tasty cheesecake lollipops. For the morning after: a special Man Maintenance program in the spa.

Back behind all the hustle and neon lies the not-long-ago regentrified South End, whose brick facades have let out their corset stays to relax behind iron fences—now home to upward climbers scampering from wine bar to gallery to designer boutique du jour.

A restaurant row is more laid-back than mired in white linen. Toro serves modern Spanish tapas—think pork belly with pumpkin, escargots, and Liberty apples—or Rioja-braised short ribs with prunes and Armagnac. Coppa is the hottest rez in town: Here, it’s Italian fare with an edge not found at Olive Garden, such as spaghetti carbonara mined with sea urchins or ravioli stuffed with calves’ brains—best-sellers, along with earthy housemade charcuterie, beef-heart crostini, sweetbread saltimbocca, and lamb’s belly with lentils and harissa.

It’s also Boston’s gayborhood, although once the baby strollers started clogging the sidewalks, the trendier boys led the migration across the bridge to Fort Point Channel—no longer grungy, as forward eateries like Drink and Sportello moved in. In fact, uberfashionable Louis Boston, proffering adornment for home and body, has moved from Back Bay to Fort Point. But you’ll find GLBT clubs throughout the city: megaglam Estate, spinning hip-hop and Top 40s tunes; The Roxy, boasting Northeast’s longest-running weekly dance club; STIX, where the food, indeed, comes speared; and Club Café, offering Manhunt Thursdays, Edge Fridays, and Mayhem Saturdays.

Remember Revere’s house, oldest in the city? It anchors Boston’s oldest neighborhood, the North End. Here’s where wave after wave of immigrants landed before moving on. But the Italians knew a good thing when they saw it, and stayed put, claiming the North End as their enclave. Wandering along Hanover, the main drag, you’ll find that English is definitely a minor linguistic curiosity among its largesse of salumerias, gelaterias, and espresso-fueled caffes, where an accordion player on break relaxed amid the clattering laptops. Yet, I prefer to veer away from Hanover’s dancing neon to dine at tinier, trendier palazzi of pasta such as Prezza, where, armed with a fruity Barolo, I feasted on short ribs in red wine sided with a lobster pancake; portobellos atop creamy polenta; and tender gnocchi served with dual sauces—rustic ragu and suave porcini cream.

With meals like that, I should hike to the airport in penance, but no: It’s only 15 minutes away, $2 on the train.

Visit to plan your own attack.

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