The Ladder District, One Step at a Time

In any case, swallow that last morsel of Boston cream pie and cross the street to tour the 1749 chapel. Its wineglass-shaped pulpit dates from 1717 and the box pews have been here from the start. Paul Revere cast the bell, "the sweetest bell I ever made," for the church in 1816, and that bell still tolls today. The tiny cemetery holds gravestones dating from the mid-1600s.

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Now, stroll down School Street and turn right, leaving the noise and mayhem of construction behind to enter 310 Washington St., the white-spired Old South Meeting House (310 Washington St., 617-482-6439, http://www.oldsouthmeetinghouse.org), built in 1729 for Puritan services. An audio tour leads you around the airy, unembellished interior, re-creating the historic town meetings held here over the centuries. This was the place to be on the night of Dec. 16, 1773, when 5,000 colonists gathered to argue over the Tory tax on tea. "This meeting can do nothing more to save our country!" declaims an anguished Samuel Adams, setting off a commotion and a band of rebels known as the Sons of Liberty, who beat it down to Griffin's Wharf, where they dump 342 chests of tea into Boston Harbor: the Boston Tea Party.

Back outside, a walk along Washington Street introduces you one by one to the ladder rungs. Venture down any one of them to find a local legend.

On Winter Street lies the Original Tremont Tearoom (48-50 Winter St., 617-338-8100, http://www.tremont-tearoom.com), whose third-floor salon has been offering tea and fortunetelling since 1936. Across the street and down a dark passageway is Boston's famous Locke-Ober restaurant (3 Winterplace, 617-542-1340, http://www.lockeober.com), which opened in 1875 for men only but now has a woman (and one of Boston's best chefs), Lydia Shire, in the kitchen.

On West Street, another prized attraction is the creaky, three-story Brattle Bookshop (9 West St., 800-447-9595, http://www.brattlebookshop.com), which lays claim to being America's oldest continually operating bookstore (since 1825).

Hiply Historic

Now look again: You'll see coolness poking out all over. Go back to Tremont Street, for example, same block as the Omni Parker House but opposite end, and stop in front of the grande dame's antithesis, the Nine Zero Hotel (90 Tremont St., 617-772-5800, http://www.ninezero.com; rooms from $215). The Kimpton boutique property is unabashedly contemporary, with nonstop techno music in the shiny metal-and-glass lobby, and whimsically decorated guest rooms.

The hotel's restaurant, KO Prime (617-772-0202, http://www.koprimeboston.com; dinner entrees from $24, although most skew much higher), opened in May. As any Boston hipster worth her skinny jeans knows, KO stands for Ken Oringer, a Boston culinary darling with a mop of dark hair and a puppy dog smile. Boston's trendiest are here, all right, sipping exquisite margaritas and sampling select cuts of steak.

Follow Tremont Street to the final rung, Avery Street, where the ultramodern Ritz-Carlton Boston Common (10 Avery St., 617-574-7100, http://www.ritzcarlton.com; rooms from $379) stakes out the luxe end of hip, which includes not just the hotel but residences, the fancy Sports Club/LA fitness center and its glass-fronted Blu restaurant overlooking Boston Common (4 Avery St., 617-375-8550, http://www.blurestaurant.com), and the up-upscale Roche Bobois furniture store. At the very least, sidle into the Ritz's newly poshed-up lobby lounge, sip a martini and observe the comings and goings of the glitzy guests.

By now you will have noticed the Ladder District's charming incongruities. Between that chichi Roche Bobois and the tony Thomas Pink men's store, old and new face off, as age-old family shops confront modern, big-name chains. A pushcart vendor hawking burritos draws toughies in gangsta garb, students in tattered jeans, Bluetoothed business professionals and string-bean waifs holding tight to their attitudes.

After Dark

The mishmash of types, sights and attractions adds a certain allure, no question. But if the Ladder District didn't have a night-life scene, we wouldn't even be having this conversation.

Up a rung from West Street is Temple Place, home to the Ladder District's two hippest restaurant/lounges. Mantra (52 Temple Pl., 617-542-8111, http://www.mantrarestaurant.com; entrees in the $24-$30 range), an 1890 bank building, opened in 2001 as a sexy, shimmering French-Indian restaurant with red suede love seats and a room-length bar that once served as the tellers' stations. Guests nosh on fresh coconut- and herb-crusted halibut and seared foie gras with spiced lobster, then stay past dinner, when Mantra's lounge scene picks up.

Across the street is the more intimate Ivy (49 Temple Pl., 617-451-1416, http://www.ivyrestaurantgroup.com; small plates range from $8 to $14), whose exposed, century-old brick walls and high ceiling contrast with the trendy velvet lounge chairs and leather banquette decor. Ivy's mood is mellower, and the menu -- creative Italian -- more affordable than Mantra's. Everyone's popping arancini (fried risotto balls) into their mouths between sips of prosecco. Wine is a deal, priced at $26 a bottle no matter which you choose from a list of 60. And so is dessert: gelato on the house. Downstairs is Cava, a dining room that morphs into a lounge as the night gets underway.