What do Andy Warhol, the Village People, and Jack Kerouac all have in common? They all cut their teeth in Greenwich Village, one of the most dynamic and colorful neighborhoods in New York City. Bob Dylan and Jimi Hendrix? They’re rumored to have jammed here, too. Paul Simon? You better believe it. And if you’ve ever seen “When Harry Met Sally,” you’ll recognize The Row, a collection of townhouses on the northern side of Washington Square Park.
Known as a haven for counterculture movements and bohemian lifestyles throughout most of the 1900s, Greenwich Village (known simply as “the Village” to locals) has some of the most wondrous attractions in NYC, from NYU and late-night pizza to indie films and legendary comedy clubs.
Here’s how you should spend your day — or a few days — in Greenwich Village.
1. Relax around Washington Square Park and NYU.
New York University doesn’t look like most other colleges and universities. Rather than having a strict campus, the buildings are peppered throughout the Village, occupying large buildings, storefronts, and residences. The closest thing to a quad that NYU has is Washington Square Park, which also happens to be one of the best parks in the city.
Known for its majestic fountain and the Washington Square Arch, Washington Square Park has played host to students, artists, poets, and visitors for more than a hundred years. Feel free to enjoy some live entertainment from the various street performers that often appear in the park, or take on a chess master in disguise in a casual game of park chess.
2. Check out world-famous comedians at the Comedy Cellar.
In a sea of poets and alternative thinkers, stand-up comedy was sure to take hold some time. Located on MacDougal Street, in the absolute heart of the village, the Comedy Cellar has showcased some of the world’s most talented comedians since 1982.
Known all over town for its infamous “drop-ins,” the Comedy Cellar is where you go if you want to see established comedians or raw up-and-comers. On any given night, the set could be interrupted by a drop-in from a superstar working on new material, ranging from Chris Rock and Dave Chappelle to musician John Mayer.
3. Grab a cup of the country’s oldest cappuccino.
Quickly becoming a unique relic of Greenwich Village’s bohemian past, Caffe Reggio is one of the city’s best spots to have coffee. Notice I said “have”, not “grab.” There’s nothing rushed about this cozy, Old-World style shop, featuring the country’s first espresso machine. So take your time and enjoy this unique anachronism.
Since 1927, Caffe Reggio has been pouring perfectly made coffees for the likes of Jack Kerouac, Al Pacino, and countless others. With walls covered in incredible, authentic school of Caravaggio paintings and a bench dating back to the Medici family, this coffee shop is a must-stop on any tour of Greenwich Village.
4. Chill out to the tunes of authentic jazz and more.
As a long-time center for artistic revolutions, Greenwich Village has been home to some of the most storied jazz clubs and venues in the country. Since the color-barrier-shattering nights of Cafe Society back in the 1940s, New Yorkers have never let the customs of the day, or a few laws, stand between them and great music.
Channel those smokey clubs of yesterday with a visit to one of the Village’s best remaining venues. The Blue Note on West 3rd Street is a tiny lounge where you can share a table with other jazz enthusiasts and listen to some of the best names in music. Get there early to secure a good seat.
To listen to some soul, R&B, funk, and more, check out another storied Greenwich Village venue: Cafe Wha? The former nightclub has hosted the likes of Bob Dylan and Jimi Hendrix and continues its history-making live music today with its house band, hosted acts, and open mic night. It’s next door to the Comedy Cellar.
5. Catch an indie film at IFC.
New York City is a genre unto itself, and the heart of indie film thrives in Greenwich Village. The IFC Center is the quintessential destination for the cinema lover in your family. IFC provides a home for new filmmakers and shows movies you won’t catch in your local multiplex. Opening nights typically feature talkbacks with the filmmakers, so this is your chance to meet the people behind the scenes in an intimate setting.
Formerly the famous Waverley Theater, birthplace of the Rocky Horror Picture Show audience participation screenings, the IFC also stays true to its roots with a midnight screening series featuring the best and most bizarre work they can find. So if indie drama isn’t your thing, consider swinging by for some late night horror fare.
Where to Eat in Greenwich Village
As an NYC local and tour guide, I can’t send you down to Greenwich Village without tipping you off to some of the best places to grab food and treats. This list will get you started.
Grab a slice at Artichoke Basil Pizza.
Artichoke Pizza is one of New York City’s most famous late-night pizza spots. At the Village location, you’re sure to see it packed with hungry NYU students who are staying out late studying or heading home after a night on the town. Their margherita slices are great, but the main attraction is the artichoke slice topped with artichoke hearts, spinach, and cream sauce.
Get a scoop of cookie dough at DŌ.
DŌ serves up various cookie dough flavors in scoop form, like an ice cream cone. Their delicious treats, which have been featured in The New York Times and Time Magazine, come in such rich offerings as cake batter, fluffernutter, and oatmeal M&M. You might be tempted to get two scoops, but trust me, one is enough.
Split a pastrami sandwich at Katz’s.
I’m bending the rules here, because Katz’s Delicatessen is right on the southern end of the Village, on the southside of Houston Street, pretty much the gateway to the Lower East Side. But trust me, even if you have to walk 10-15 minutes, it’s worth it.
Established in 1888, Katz’s is about as authentic as it gets in New York, and you can’t get this experience anywhere else. They cure their corned beef and pastrami for 30 days, resulting in a tender, succulent meat that they layer on top of pillowy rye bread. I don’t even like pastrami, and Katz’s serves up one of the best sandwiches I’ve ever had.
Have a picnic in the park.
Any of the stops above work great if you want to take them to go. When the weather’s nice, a picnic at Washington Square Park can’t be beat.
Greenwich Village: Your New Favorite NYC Neighborhood?
A trip to NYC wouldn’t be complete without visiting Greenwich Village. From counterculture to college campus, the neighborhood has cemented itself in NYC history over the decades.
Whether you spend your time there lounging under a tree in Washington Square Park, laughing until it hurts at the Comedy Cellar, or channeling your inner poet over a cup of coffee, the Village is sure to capture your heart.