The Upper West Side’s Shady, I Mean, Shanty Past

Before Seinfeld made the Upper West Side the playing grounds for a show about nothing, the UWS was a shantytown of squatters

After Central Park was built in 1853, thousands of lower-income tenants were displaced and created makeshift villages and shacks along the West Side. It wasn’t until the end of the 19th century when large developers (no, not Whole Foods) started building grandiose apartments (like the San Remo that Steven Spielberg calls home), that pushed squatters out and brought yuppies in. I guess you could say yuppies were the hipsters before hipsters?

Photo via Public Domain of Shantytown in 1880.

The Upper West Side Now

You get a lot of the touristy crew around the Museum Of Natural History and Central Park, but other than that, the UWS is one of those neighborhoods that feels neighborhood-y. Maybe it’s the 79th street Farmer’s Market that takes place every Sunday or the cute brunch spots like Jacob’s Pickle that line up Amsterdam Ave, either way, it’s a place definitely worth exploring on a sunny Sunday with friends who won’t complain about going up past 14th Street.

Our guide this week is the swing dancing, Spanish-speaking, business professor (he earned the first doctorate ever in positive psychology), and start up advisor, Orin Davis aka smartest guy I know. 

Having lived in the UWS for the past 5 years, Orin knows the ins and outs and showed us some of his very favorite local hangs. Follow @ciaooomag and @drorindavis on Instagram!


Photo via Foursquare


When You’re Broke as a Joke
Literally everything here is $2. Don’t ask me how they do it. Espresso? $2. Italian hot chocolate? $2. Chocolate chip cookie? $2. Soup of the day? $2!!!!

Photo via Sideways

Grill 212

This authentic Yemenite and Middle Eastern restaurant serves up some of THE most explosive flavors. A husband and wife team run the shop and blend up their own “secret” spices daily and make an incredible homemade hot sauce called S’chug (click to hear pronunciation). Go for the Yemenite Soup, Kibbeh, Hummus with Shwarma, Moroccan Cigars and Kofta. BEST HUMMUS & FALAFEL I’VE EVER HAD.  BUT there are Israeli drinks in the cooler here that are a must try! Including the Malted Beer. PS- tell Ricky we sent you, and she’ll take care of you!


When You’re Digging Some Sweets
The original location was on the same street Edgar Allen Poe wrote “The Raven” for 25 years before it moved here. Something about the ambience here is kitschy meets adorable. The ravens above the door. The massive painting of Edgar Allen Poe. The cracked ceiling and brick walls. It’s a great spot for a date or wine with friends- definitely recommend coming here for dessert and drinks. The cheesecake is DI-VINE.


Irving Farm New York

The lines get long, so be wary, but it moves fast. The shop stretches back but you might have to wait a bit to get seating. It’s a good spot to meet friends to begin your adventure!




Flying Tiger

Tchotchkes and knick-knacks, there are all sorts of random things to buy here for pretty cheap. Kitchenware, Halloween fish masks, art supplies, it’s like a junk drawer at grandma’s house. Quality might not be the best, but hey, you get what you pay for.

Book Culture

This book shop has “blind dates with a book” where the books are wrapped in brown paper. You don’t know what you get until you open it! There’s a note with similar book titles on the cover, and each book is similar in style to the suggestions listed on the cover.


This grocery store has brie cheese for $1.99!! Way cheaper (and smaller) than Zabar’s, but if you’re going for the experience, or to find something special, hit up Zabar’s.


Spanish Portuguese Synagogue

The Spanish Portuguese synagogue is the oldest congregation in the US, and the building is beautiful. You can book and attend a free tour on their site.

Customers relax at the cafe at the 79th Street Boat Basin in Manhattan, New York on August 24, 2005. The 79th Street Boat Basin is the only city-operated marina in Manhattan and has a waiting list of more than five years. Photographer: Jennifer S. Altman/Bloomberg News

79th Street Boat Basin

Most tourists go to Central Park, but locals also hit this one and I love the views. Plus in the summer time it’s a bar!

Symphony Space

Most people go to Broadway (42nd st.), but this place is so far uptown people don’t even realize it’s up here. Tickets are $21 for ages 30 and under and $24 for regular tickets.

Chau Mui

Chau is the original New York City stoop kid who cut her teeth hanging out in Union Square, ate soup dumplings in Chinatown and explored this great city by train, foot and everything in between.

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