The night walk

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City Hall Park

Start A, C to Broadway–Nassau St; J, M, Z, 2, 3, 4, 5 to Fulton St
End 1 to South Ferry
Distance 3.75 miles
Time 3.5 hours
Calories burned 375

1 New York after dark needn’t be X-rated to be interesting. In many neighborhoods the late-night hours are monumentally serene—a time when the city relaxes and opens itself up to exploration. Chinatown and the Financial District, which teem with shoulder-to-shoulder bustle during the day, are peaceful by moonlight—not to mention steeped in rich city history. Start at the South Street Seaport (Fulton St at South St, Pier 17; 212-732-7678). Its annoying mall-ness fades at night—even the mime knocks off around 10—and it’s easier to enjoy the docked schooners and views of the illuminated Brooklyn Bridge.

2 Walk up Fulton Street and take a right on Front, where inviting bars and restaurants are nestled in old brick buildings. Around the corner on Dover Street, the Bridge Café (279 Water St at Dover St, 212-227-3344) occupies the site of the city’s oldest continuously operating bar. Along with a drink, try the blue-cheese soufflé.

3 Continue up Dover and hang a right on Pearl, which takes you into Chinatown. Bear right at St. James Place. Whiffs of seafood and overripe lychee signal the change of ’hood. On East Broadway, stop at White Swan Bakery (at Forsythe St, no phone) for Asian pastries and all your fish-oil needs.

New York Stock Exchange

4 Keep chugging up East Broadway to 169 Bar (169 East Broadway between Jefferson and Rutgers Sts, 212-473-8866), formerly known as the “Bloody Bucket” for its frequent fisticuffs. These days the crowd is docile and eclectic, and there’s live music every night.

5 Head west toward Bowery and start walking downtown. Only on Pell Street can you get a “foot rub” as late as 1am, at Foot Heaven (16 Pell St between Bowery and Mott St, 212-962-6588). You must call before 11 to line up your massage.

6 Take a quick right onto Mott, then a quick left onto Bayard. Linger for a moment by karaoke bar Winnie’s (104 Bayard St between Baxter and Mulberry Sts, 212-732-2384); across the street on Baxter, you might see perps getting dragged into a police holding cell by the fuzz.

7 Next, wander south and west to Centre Street and walk downtown to City Hall Park. The southern gates are open all night, offering visitors a surprisingly scenic respite amid the soft glow of oil lamps above the fountain.

Bridge Café

8 With its screened fences and ultrasanitized memorial photos, Ground Zero is no longer the emotional gut-punch it once was. Still, if you want to remember and reflect, this is the time to walk over to Church Street and do it. One block east on Broadway, behind the Century 21, is an area that was the Fifth Avenue of its day—a snazzy commercial stretch frequented by the finest turn-of-19th-century ladies. Now, it has a Burger King.

9 Walk south on Broadway, passing Trinity Church (89 Broadway at Wall St, 212-602-0800) and the graveyard where Alexander Hamilton is buried. Challenge him to a duel and feel superior.

10 Across from Trinity, Wall Street at night is an urban canyon, and wears its history proudly (Washington, memorialized in sculpture, took his first oath of office here). Say hello to the security guard who stands watch at The New York Stock Exchange (11 Wall St at New St, 212-656-3000) from 6pm to 6am. He’s lonely.

11 Meander leisurely south (glancing at Fraunces Tavern, where George Washington bid farewell to his soldiers during the Revolutionary War), taking care to traverse the tight cobbled streets that evoke the small trading-post town of 200 years ago. End at South Ferry, at the tip of the island. Hard-core insomniacs should take the Staten Island Ferry over and back. It runs every half hour (or every hour from 1:30am to 5:30am), and from the water the skyline rises right in front of you, a cheesy New York moment worth the cliché.—Dustin Goot

Our featured walks:

• The Zen walk: Get back to nature—without spas or drum circles.
• The stoner's walk: Blaze up and turn off Aqua Teen for a real-life trip. Wait, what’d you just say?
• The romantic walk: Yeah, it includes a sunset. (You won’t be making fun when you get lucky.)
• The night walk: It’s quiet, but not too quiet—some New York sights are best seen in the dark.
• The Queens Boulevard walk: Conquer the Avenue of Death and claim your reward: beer and a fantastic view.
• The dog walk: Take your furry confrere on a deluxe gambol that’s good for both of you.
• The other Fifth Avenue walk: There’s no Saks, and that’s what we like about this multiethnic stretch in Brooklyn.
• The Met walk: Don't let this giant art palace daunt you – hit the highlights, then let tourists descend.

Plus:

• Park avenues: Central Park offers more than half-naked Frisbee players in Sheep Meadow—witness rare birds, waterfalls and (bonus) free coffee on these five expert walking tours.
• Walk of shame: Our hot fuzz tickets slow movers, phone talkers and guy-who-stops-at-top-of-stairs.
• Submit your own walk: Cartography is fun. Show us your favorite ambles using Google Maps.