west-village-street-evening.jpgGreenwich Village
Greenwich Village is my favorite neighborhood in New York. I know that’s a predictable thing to say. I know it’s the answer every tourist gives. But I’ve walked these streets hundreds of times and they still make me feel something, which is more than I can say for most of Manhattan at this point.
This is a walking route I’ve done so many times I could do it with my eyes closed. It starts at Washington Square Park and ends at the Hudson River, with stops for comedy, coffee, history, cheese, and one of the best restaurants in the city. The whole walk takes about two to three hours depending on how long you linger, and you will linger.
Let’s jump in!
Start at Washington Square Park
Every good Greenwich Village walk starts here. The arch, the fountain, the NYU students everywhere, the guy who’s been playing jazz piano in the southeast corner for what feels like decades. Washington Square Park is chaotic and loud and full of people doing wildly different things all at once, and that’s exactly why it works.
Spend 15 to 20 minutes here. Sit on the edge of the fountain. Watch the street performers. There’s usually someone doing impressive things with a guitar, and there’s always someone playing chess in the southwest corner if you want to lose $5 and your dignity in four minutes.
Fun fact. The arch was originally built in wood in 1889 to celebrate the centennial of George Washington’s inauguration. They liked it so much they rebuilt it in marble. That’s the most New York thing I can think of. “We built a temporary thing. It’s beautiful. Make it permanent.”
Walk South to Comedy Cellar
From the park, walk south on MacDougal Street. Within two blocks you’ll hit the Comedy Cellar at 117 MacDougal Street. This tiny basement club is where Jerry Seinfeld, Chris Rock, Amy Schumer, and Dave Chappelle have all done surprise drop-in sets. On any given night, a famous comedian might show up unannounced.
Tickets are $14 to $24 plus a two-drink minimum. Book online in advance because they sell out. Even if you’re not catching a show, it’s worth walking past and noting the address. This little door in the sidewalk is one of the most important comedy venues in American history. No exaggeration.
Caffe Reggio for the Oldest Cappuccino in NYC
Right next door at 119 MacDougal Street. Caffe Reggio claims to have served the first cappuccino in the United States, back in 1927. Whether or not that’s technically true (it’s hard to verify), the cafe is gorgeous. Dark wood, old paintings, an antique espresso machine from 1902 that still sits on the counter.
A cappuccino is $6. The vibe is worth more than that. This is one of the last old-school Village cafes that hasn’t been turned into a Sweetgreen. Sit in the back room, drink your coffee slowly, and pretend you’re a Beat poet for ten minutes. Nobody will judge you.
dante-cocktail-bar.jpgDante · Greenwich Village
The Stonewall Inn and Christopher Street
Walk west on Minetta Lane (more on that street in a minute) and zigzag your way to Christopher Street. At 51-53 Christopher Street, you’ll find the Stonewall Inn, where the 1969 uprising that launched the modern LGBTQ+ rights movement began.
It’s a National Monument now, the first one dedicated to LGBTQ+ history. The small park across the street has the George Segal sculptures of same-sex couples. It’s a powerful, quiet spot in the middle of a busy neighborhood. Take a moment here.
Christopher Street itself is lively and fun to walk down. Lots of small shops, rainbow flags, and a real sense of community that’s survived decades of gentrification.
Bleecker Street. The Main Event.
Head south to Bleecker Street and turn west. This is the stretch that most people think of when they picture Greenwich Village. Record shops (Generation Records at 210 Thompson is a must if you’re into vinyl), boutiques, and some of the best food stops in the neighborhood.
The essential Bleecker Street stops. Murray’s Cheese at 254 Bleecker (the grilled cheese sandwiches are $14 and absurdly good). Rocco’s Pastry Shop at 243 Bleecker (cannoli, $5). Bleecker Street Pizza at 69 Seventh Ave South (the nonna slice, $6, don’t skip it).
If you’re a West Village completist, the side streets off Bleecker are where the real charm is. Perry Street, Charles Street, Bank Street. Brick townhouses, tree-lined sidewalks, window boxes with flowers. It’s aggressively picturesque.
About Those Confusing Streets
A quick note about getting lost. You will get lost in Greenwich Village. The street grid here predates the Manhattan grid system, so instead of nice numbered streets, you get West 4th Street crossing West 10th Street (yes, really), Waverly Place intersecting with Waverly Place (also yes, really), and streets that curve for no apparent reason.
This is part of the charm. Use Google Maps when you need to, but also let yourself wander. Some of the best things I’ve found in the Village happened because I was lost and turned down a random street. That’s how this neighborhood is designed to work.
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Minetta Lane. A Tiny Detour Worth Taking.
Minetta Lane is a one-block curved street between Sixth Avenue and MacDougal Street, and it’s one of the oldest streets in Manhattan. It follows the path of Minetta Brook, a stream that used to run through this area (it’s still flowing underground, which is wild to think about).
The Minetta Tavern is here at 113 MacDougal, and if you can get a reservation (good luck), the Black Label Burger ($36) is one of the best burgers in New York. It’s made from dry-aged beef and it’s absurd. If you can’t get in, just walk the lane and appreciate that you’re walking above an underground stream in the middle of Manhattan.
Via Carota. No Reservations, Always a Line, Always Worth It.
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51 Grove Street. Via Carota is, in my opinion, one of the five best restaurants in New York City. It’s an Italian restaurant run by chefs Jody Williams and Rita Sodi, and they don’t take reservations. You just show up and wait.
The wait can be 45 minutes to two hours on a weekend evening. I know. But the carciofi (fried artichokes, $21) are transcendent. The tagliatelle ($26) is perfect. The insalata verde is the best salad I’ve ever eaten, and I’m not someone who gets excited about salad.
My strategy. Go on a weekday. Arrive at 5:15 PM, right when they open for dinner. You’ll usually get seated within 20 minutes. Bring a friend who won’t complain about waiting. This is worth it.
End at the Hudson River Greenway
From Via Carota (or wherever you end up on the western edge of the Village), walk to the Hudson River. The greenway path runs along the water and it’s one of the best places in Manhattan to decompress after a long walk.
If it’s sunset, you’re in for something special. The sun drops behind New Jersey (the one nice thing Jersey has going for it, sorry) and the light on the water is gorgeous. There are benches everywhere. Runners and cyclists will zoom past you. The Statue of Liberty is visible to the south.
This is where I like to end the walk. Sit on a bench, look at the river, and process the fact that you just walked through one of the most historically and culturally important neighborhoods in America. Not bad for an afternoon.
If you want more walking routes around the city, I have those too. But this one is my favorite. Every single time.