Happiness is a cold pillow on a hot summer night. It’s the sound of exactly three seagulls on a slightly foggy morning, a book that’s only occasionally skimmable, or a leisurely meal in a big green booth at Upland. Happiness is also a little overrated, and so is Upland.
Don’t get us wrong, we like Upland. Shortly after it opened in 2014, we gave it a 9.1 - and we’ve had plenty of good meals there since. But some places age better than others, and a “California-inspired” spot that shares a couple of chromosomes with CPK won’t stay prom queen for long. Now that the glow has worn off and the food has taken a slight dip, Upland is less of a must-visit and more of a generically classy option for when you’re planning an important group dinner and want to please as many people as humanly possible.
Whether you’re dining with someone who only eats variations of bread and cheese or a friend who considers little gem salad a comfort food, pretty much everyone will be happy here. Entire sections of the menu are devoted to pizza and pasta, and Upland’s versions of these things are sort of like backups on an Olympic water polo team. They aren’t the absolute best in their class, but they get the job done. And if you need a main, there’s just about every type of protein a second-tier friend or parent-in-law could hope for. Just know that the portions are surprisingly large, and the entrees are less reliable than the pizzas, pastas, and smaller plates - so you might find yourself slogging through an oversized serving of fatty lamb shoulder with a confusing amount of bibb lettuce on the side.
Those larger plates usually hover around a B-, but the space itself is a solid A. The dining room has high ceilings, hardwood floors, and the kind of blue-and-white checked tablecloths that make you think of sunshine, fresh-cut grass, and uncoordinated children running through sprinklers. It has a wholesome, Norman-Rockwell feel, and all the way in the back, you’ll find a shelf of preserved lemons in big glass jars. They’re illuminated by soft yellow lighting, and while you observe this display from your plush green booth, you might get the sense that you’re dining inside of Martha Stewart’s doomsday bunker.
Upland is a comforting place, and the constant crowds make it seem trendy, relevant, and exactly like the kind of spot you’d want to talk about in an elevator full of coworkers. And this helps make up for the occasionally underwhelming food. You walk inside, see a packed bar area, catch a whiff of rosemary drifting out of the open kitchen in the back, then see a bunch of servers in gingham pacing around a dining room that could be the world’s nicest Williams Sonoma. It’s an unimaginative version of heaven - but it’s heaven nonetheless, and you’ll be happy here.
A dinner at Upland always starts with a free loaf of potato bread. It’s incredibly fluffy and about the size of a small brick, and it steams when you cut into it. There’s also a tiny side of butter covered in minced chives - and we truly appreciate all of this. It’s an extremely nice gesture, and it makes us want to be better people.
Some days, this is perfectly dressed and one of the better caesar salads in the city. Other days, it’s a pile of damp leaves with uneven pools of dressing. If you decide to go for it, that’s brave of you. Just mentally prepare yourself for potential disappointment.
The pizzas at Upland aren’t going to change your life - but, then again, you don’t come to Upland for a life-changing experience. You come because it’s crowd-pleasing and reliable, and nothing exemplifies that more than this margherita pizza. The crust is thin, fluffy, and slightly crispy, and if you’d like to go for a slight upgrade, you can get the clam pie instead.
This is, truly, a very large fried mushroom. It even works as an entree if you don’t eat meat - but we prefer to split it with someone at the beginning of a meal, because a huge mushroom gets kind of boring if you’re taking it down by yourself.
The single best thing at Upland, this burger has two thin patties, plenty of cheese, and a sesame bun that squishes in your hands like a Nerf football. It’s like a fast-food burger, but one that grew up, moved out of the house, and got a nice job in the city. Order it.
Chicken might sound like a safe bet to you, but you can go ahead and skip this (and most other entrees at Upland). It’s dry and generic, with some weirdly smokey labne and a heap of charred swiss chard on the side that tends to just taste burnt. And yes, they do call it “charred swiss chard.”