Hell’s Kitchen

Start: 35th St and Eighth Ave
Distance: 1.8 miles
Time: 2 hours

1. Once a stomping ground for gangs and prostitutes, Hell’s Kitchen has cleaned up its act, but you don’t have to search hard to find reminders of this neighborhood’s sinister and strange past. Start out at the New Yorker Hotel (481 Eighth Ave at 35th St; 212-268-8460, newyorkerhotel.com), which, when it was built in 1929, was the largest hotel in the city. The Art Deco beacon closed its doors to guests in 1972, but its owners (the Unification Church) renovated and reopened the space in the early ’90s, making it something of a destination for tourists. Though bustling, the lobby is pretty quiet these days compared with the ’30s and ’40s, when the hotel was a regular stop for big bands and home to eccentrics such as Nikola Tesla, the engineering genius who devised AC electricity—and also tried to invent a time machine. If only he had succeeded: We could all go back and watch Benny Goodman and His Orchestra perform in the Terrace Room, a popular downstairs nightclub that featured a miniature ice-skating rink.

2. Now that you’ve connected with the past, head over to Ninth Avenue and 34th Street, where you’ll pass St. Michael’s (424 W 34th St between Dyer and Ninth Aves, 212-563-2575), a Catholic church built in 1906. (Fun fact: The statue of the titular saint in front was stolen in 2008, then turned up hours later in a parking lot on 33rd Street.) Go north on Ninth until you reach Mike Dimitriou’s shrine to forgotten treasures, the Thrift and New Shop (602 Ninth Ave at 43rd St, 212-265-3087), a trove of used books, antique jewelry and knickknacks. You want German Gloebel porcelain bird figurines ($19.95)? He’s got 20.

3. Next, soak up (or gobble down) some local flavor at 87-year-old Poseidon Bakery (629 Ninth Ave between 44th and 45th Sts, 212-757-6173). Owner Lili Fable once served 5,000 pieces of its famous spinach pie ($4) to hungry New Yorkers at the first-ever International Foods Festival in 1973. Tip: Show up around 11am and you might be able to snag a piece of its flogera ($3.50)—a sweet custard-filled pastry—hot out of the oven. Yum.

4. Go west on 46th Street and follow it to the Matthews-Palmer Playground (W 46th St between Ninth and Tenth Aves). Looks peaceful now, but on August 29, 1959, a gang-related rumble led to the stabbing of two innocent bystanders by one Salvador Agron, who sported a sinister black cape. Paul Simon later based his failed musical The Capeman on the event.

5. Time for a pick-me-up, Puebla-style: Tehuitzingo (695 Tenth Ave between 47th and 48th Sts, 212-397-5956) looks like a tiny Mexican grocery store, but walk through the front and you’ll also find a tiny restaurant. This family-run taqueria has everything you’d want in a Mexican joint: mariachi music, a narrow, neon-lit bar stool seating area, and delicious tacos and treats—like the squash blossom quesadilla ($2.75).

6. Once known as the Sunbrite, Druids Bar (736 Tenth Ave between 50th and 51st Sts, 212-307-6410) used to be the dingy haunt of the ruthless Irish gangsters the Westies. They’re gone now, but the stories live on, however apocryphally. Did a guy called Paddy Dugan really get his nuts cut off and put on display in a milk carton behind the bar? “I don’t really pay attention to that stuff,” says Irish owner Michael Younge. Spoken like a true brigand.

7. Head north on Eleventh Avenue, where, on weekday afternoons, you can queue up outside the doors of The Daily Show with Jon Stewart (733 Eleventh Ave at 52nd St; 212-586-2477, thedailyshow.com), which lets in its studio audience on a first-come, first-served basis. (Taping usually happens around 5:45pm, but sources at the show recommend arriving around 3pm for a shot at a ticket—they go fast). If that doesn’t work out, try crossing the still-cobblestoned section of 52nd Street between Eleventh and Twelfth Avenues to DeWitt Clinton Park, founded in 1905 and named after the 1800s New York City mayor who pioneered the Erie Canal. The gorgeous rock garden on the south side is dedicated to Clinton’s first wife, Maria.

8. Eleventh Avenue used to be on the edge of Manhattan, before Twelfth Avenue was built on top of a landfill. Therefore it seems appropriate to end up here, on the former frontier, at one of New York’s oldest bars, the Landmark Tavern (626 Eleventh Ave at 46th St, 212-247-2562). Built in 1868, when Hell’s Kitchen was rolling farmland and the grid system a relatively new concept, this place originally served pints for just a nickel apiece. On Mondays, you can sit down to bangers and mash ($12) and a single malt ($10.50 and up) while local bands strum traditional Irish tunes. Almost like the old days!

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