You don’t need more than one day, trust me. But there are some cool places in this mostly unremarkable neighborhood. I don’t really think of Flatiron much, although I now find myself in the area every weekend for appointments with my therapist. I also love nostalgia as much as I hate it, and I lived close to Madison Square Park in college. All and all it was an amazing couple years, with the exception of the semester I lived with the most disgusting people I’ve ever met (and I say this despite being somewhat disgusting myself). They left soggy food and spoons in the shower, ate all my weed brownies, licked the frosting off my cupcakes then put them back on the plate, left hair extensions in the massive puddle of water that was the bathroom floor, and broke a glass full of honey and left the pieces all over the floor causing me to cut my foot badly. Among many other things. My parents could barely be inside the place when they visited. Apparently I had gone nose-blind to the pervasive smell of cheese throughout the suite.
Anyway, lots of memories. Disgusting humans aside, my years in Flatiron were some of my best, so being back there is a mixed bag. I have a passionate but toxic relationship with the past. Here’s my short list, tinged with nostalgia, of Flatiron’s best.
Madison Square Park / Flatiron Building: Obvious hotspot in the neighborhood. Great for photos or just hanging out. There’s also a Shake Shack, which I literally went to like four times a week in college. This is a quick stop, unless you wanna hang around. Eat a burger on the ground in the park, but save room for lunch.
Momofuku Milk Bar: A quirky sweet shop from the same restaurant group as Noodle Bar. Milk Bar has been a favorite of mine since college, when it was just a little store front. Cereal Milk ice cream, which tastes just like the milk left in a bowl of cereal, is their best thing IMHO.
Eataly: Eataly was very first restaurant I ate at when I moved to New York. It evokes a sense of nostalgia even if you haven’t been there before…like an almost there memory of a past life in which you grew up in Tuscany and went to the market with your mother on weekends to sell olive oil. Eataly is essentially a massive foot court and grocery store, with sit-down restaurants inside as well. Any kind of Italian food you could want. Authentic as it gets outside Italy.
The Ace Hotel: I’ve gone there to study and work since I was nineteen. At the time it felt like a very glamorous place to be, and sometimes it still does. It’s pretentious, but the lobby has free wifi, a great bar, plentiful comfy seating, and a slightly gothic energy—never fails to increase my productivity. I also take out of town visitors here a lot. There’s a great in-lobby menu, and the rooms are pretty cheap if you’re looking to stay in the City. At 29th off Broadway. Great place for happy hour, dinner, or late night cocktails.
230 Fifth: Rooftop bar with incredible views of the Empire State Building. Good food, good drinks…a little obnoxious (they serve frosé) and touristy (it’s a rooftop bar with incredible views of the Empire State Building). But, it’s a rooftop bar with incredible views of the Empire State Building.
Museum of Sex: Tentatively recommend. This is as wild as it gets in Flatiron. It’s really not that wild, and it’s a ripoff. Exhibits do change semi-regularly though, and there have been some good ones. It’s a fun place if you’ve got an hour to kill. They have a great gift store. Also there’s a moon bounce full of inflated boobs. They once had a rock wall where all the handholds were shaped like penises (penisi?), so it can be amusing in an immature way. There are also a lot of to-scale sculptures of animals having sex. Flatiron’s greatest. To be clear I don’t spend $20 to get into MoSex on a regular basis, but to be completely honest I have been like a dozen times. It just kind of happens.