Don’t miss the rest of this series HERE. In this instalment I’ll walk you through how I usually approach eating in New York City following my personal philosophy of embracing the cliché.

I usually fly out on a Friday after work so, by the time I get to the city, it’s pretty late. But, because your hotel is in midtown (see Part Two: Logistics), absolutely everything will still be open (one of the best things about New York by far) so it’s time for late night trash food. Being Canadian, we don’t yet have everyday access to Shake Shack so that’s my go-to late night treat upon arrival but they’re expanding too quickly to keep their only-in-New-York status so instead I’m going to tell you to go full cliché and grab a slice of pizza. My favourite pizza in the city is still coming up but it’s a proper sit-down restaurant and the trashy single slice variety is the true icon so slide into whatever sketchy looking place you see and eat standing up. A real New Yorker would likely recommend Joe’s but, to be honest, I kind of think fast, greasy pizza is pretty consistent wherever you go. They take it seriously so anywhere really bad’s been run outta town.


My actual favourite pizza in town is at John’s. There are a few of them throughout the city but, perhaps predictably, I’m going to tell you to go to the one in Times Square. Yes, it’s all part of my midtown propaganda (you have to go all the way to Tokyo to find a city with anything like Times Square, icky though it is, so see it while you’re there) but John’s of Times Square also fulfills the restaurant equivalent of staying in a hotel with some historic or architectural significance. The restaurant is an old church that was restored years after being abandoned so its walls reflect the four pillars of New York City: historical beauty, 20th century grime, self importance, and pizza. It’s also big, busy, and has a lot of rules, what’s more New York than that? The main rule is that they don’t do slices, only full pizzas (plus a full menu of apps, pastas, and other entrées), which is actually a great rule because I’d choose a fresh whole pizza made to order over a reheated slice any day. Pretty much all the appetizers (particularly the garlic rolls and fried ravioli) are great and I prefer to keep it simple for the main and get a margherita and bianca for the table. I’ll never not find it annoying that New Yorkers claim to have invented pizza (this is literally something I was told on a food tour once. While food tours are usually a really fun way to experience a city, New York food really doesn’t require explanation) but I’ll admit that John’s is pretty great.


It’s worth pointing out the pattern in my food recommendations. A lot of them are positioned less than a 10 minute walk to most Broadway theatres. More on this in the next instalment but you’ve gotta be walkable to the theatre. I have my guilty pleasure favourites, sure, but food is really not the main appeal of New York. I never want to spend a whole night centered on where I’m eating dinner, at least not in New York. So John’s, for example, was a place I once left at 1:52pm and still made it to the matinee of Moulin Rouge on time. In most cases, this is what I’m looking for from a New York restaurant: cliché tourist food and proximity to somewhere else I want to be.


On that note, I never visit New York without a stop at Junior’s Cheesecake (“the original one in Brooklyn?!” my born & bred New Yorker friend asks without fail; “nope! The one near The Lion King!”). Obviously the cheesecake is the reason for the stop (ask for caramel sauce) but Junior’s is also an acceptable-if-not-ideal spot to get your classic New York deli fix. All the hubbub is about pizza and bagels (two foods that literally exist everywhere in North America) but what New York actually does better than anywhere I’ve ever been is Jewish deli. I can’t leave town without a brisket sandwich. The one at Junior’s is a little dry but it’ll do when you need your deli fix but you also need to make it to the Majestic by 8pm. The hilariously secular cheddar & bacon-smothered latke is another indulgent favourite on the menu, and a chocolate egg cream is mandatory. This is the food that’s, to me, truly New York (I’ve never even seen an egg cream anywhere else). It doesn’t have to be Junior’s* but prioritize sandwiches over pizza for proper food tourism. (For the record, I did visit the original Junior’s on a recent trip that was more Brooklyn-focused than usual. I stand by my support of the one near The Lion King).


*If you have the time, and I mean a lot of time, one of the best things you can do food-wise in New York is Katz’s. It’s the oldest deli in town and famously the home to When Harry Met Sally’s iconic “I’ll have what she’s having” scene (so, again, food + point of interest; two birds). Problem is it’s way out of the way and there’s always a truly insane line to get in. You have to decide that Katz’s is what you’re doing that day because it’s not a quick bite on the way to something else kind of place. So, while it’s a great time and great food, it’s only something I’d put on the list if you’re staying more than a couple days or you’re planning a return visit.


Finally, this one’s more of a specific recommendation for non-Americans but I never visit New York without stopping at 5 Napkin Burger. If you’re American, chances are there’s a decent burger place somewhere near you so this is really not a necessary New York tourist stop but I always put it on my list because Canadians are legally prohibited from serving a great hamburger (literally, there’s a law that says we have to overcook the patty) and 5 Napkin has the best burger in New York (and New York is the American city I visit most often). The Hell’s Kitchen location is incredibly convenient and they actually take reservations, which is rare and makes life so much easier when you’re sticking to the crowded section of a crowded city. As a backup, I also like Bill’s. The service is lightning fast and the s’mores milkshake lives rent free in my dreams. Plus its proximity to 30 Rock makes it yet another great 2-for-1 special.


I’ve had better meals in New York than all of these places (well, nothing’s better than 5 Napkin Burger), but I’ve never returned to any of those restaurants. Because we’ve got great restaurants at home. This list is really about eating the food that’s baked into a place’s identity. There are a few others that are considered New York classics (knishes from Yonah Schimmel; black & white cookies; Gray’s Papaya is admittedly both fun and incredible value) but they’re not as much my cup of tea and this is a guide to how I do New York. If you’re in town for more than a few days, maybe take one night to visit some really great restaurant run by some really hip chef (Miss Ada in Brooklyn is A+) but if you’re doing the one weekend thing, these are my unsophisticated go-to’s that always make me happy.