Checkerboard Pizza

Picked up two 18" pizzas; a Margherita and pineapple and pepperoni. This was on a Saturday around 2 pm and it was EXTREMELY busy in Pine Street Market. For those who don't know, Pine Street Market is like an elevated food court with high end food offerings and open table seating. We couldn't find seating so my friend and I decided to have a tailgate party in the parking lot (hence the lousy pictures taken in the back of his Subaru). Parking is also dicey around that area, especially on the weekend with Saturday Market. The pizzas cost $22 for the Margherita and $30 for the pineapple and pepperoni for a grand total of $52. They also offer 12" pizzas, pizza by the slice and they also deliver. The Margherita had a very strong basil flavor in sauce and the mozzarella was fresh and delicious. I just wish there was a just a bit more mozzarella sprinkled on the pie. The pepperoni and pineapple was great, but I feel it's kind of steep at $30. The sauce didn't have a strong basil flavor, but it was a sweet tomato sauce that I like. The toppings were plentiful but not overkill. The star that shines for these pies is the crust. A slight chew with a light and crunchy outside. The inside is soft and almost pillowy. It's seriously the best pizza crust I've encountered. Overall, if you're down at the waterfront I'd pick up a slice or if you want leftovers and feel the price won't hurt your wallet, go for an 18". It's the best pizza I've had downtown thus far.

I had one slice each of Pepperoni and Brooklyn (capricola, pickled jalapeño, and honey). Both slices were great! The pepperoni curled up and cupped the grease...always a nice touch! Very crispy crust, with just the slightest hint of char. My first two slices of Portland pizza were excellent! EDIT: Bonus points for Apple/Google Pay!

By far the best pizza in Portland. They put emphasis on the crust with simple toppings. I would recommend a slice of Brooklyn. So good even without the capicola. This pizza has ruined me for all other pizzas. Good folks and great slices.

Really very good pizza slices are big and taste amazing, I live in New York and I would say these are better

I’m so happy I found this place! Checkerboard Pizza is my new go-to pizza place in Portland. Probably the best I’ve ever had! The service is always friendly and Pine Street Market (where they’re located) is fun to visit. Try calling and ordering ahead of time or use the Caviar app (for both pickup or delivery options) to skip the line if you want a full pizza. Checkerboard’s sauce and dough are the best I’ve had hands down. Always so fresh, thin, light and crispy. Delicious! The Brooklyn is awesome if you like sweet and spicy flavors and the sausage pizza is something special. Pepperoni is great, too. You can’t go wrong with any of their pies!

Really great pizza and good selections. They also have a good selection of French pastries.

I rarely rate places lower than 4 stars. All I can say is that I got the sausage slice which LOOKED amazing. However the taste left something to be desired. The sauce just tasted like marinara and the slice was smaller than what I get at any other spot. The cheese was uneven and only covered about half the slice. The crust was incredible, but this was NOT New York style. This is in its own category. I’d say the crust was closer to something of a baguette, just much thinner. It flaked and came apart. Nothing wrong with it as it tasted great, however again, this is not NY style. All that to say, the slice as good, but it left me disappointed. I’d easily go to Straight from New York over this spot if you want real NY style pizza.

I did a back to back pizza slice eating day. Checkerboard has by far the best slices in Portland. It's gotta be the best slice I've ever had, actually. Great slightly charred crust, perfect tomato sauce & funky cheese with a little bit of a bite to it. 5/5, easy.