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Loved It, Hated It: Uptown Pie Company

By Caitlin Klein in Food on Apr 6, 2011 6:00PM

Two of your favorite Chicagoist foodies, Minna and Caitlin, teamed up to try the new Uptown Pie Company, an addition to Wilson Yard's Cupcake Gallery. Baker/owner Darius Williams also added an expanded seating area to the existing space. Minna loved it. Caitlin hated it. Find out why, grab a slice, and let us know what side you fall on.

The Cupcakes
Minna: The cupcake craze has made me a bit of a cupcake snob, and I only accept the best from a cupcake. I mean, the works. I want a light fluffy batter with a lighter whipped variety of frosting and, whenever possible, filling in the middle made with fresh berries or chocolate ganache. Stale cake bases, semi-hardened frosting or less than a tablespoon of “filling” are just simply unacceptable. On this snob’s scale, the cupcake gallery fairs pretty well, with a good frosting to cupcake ratio and a hefty menu of “filled cupcake” flavors. And as with any urban bakery, the Cupcake Gallery adheres to the unwritten rules of dietary restrictions, offering both gluten-free and vegan cupcakes alongside their regulars. The only downside, don’t expect to get what you want when ordering from the store, as selections are limited to “made that day” goods only. If you really want to delve into their menu, order ahead and choose a variety.

Caitlin: I hate the cupcake craze. You want me to pay $3-$5 for a fist-sized glob of frosting? Uh, no, buddy. Sorry. The cupcakes are what this place was founded on, and I think it should have stayed that way. The cupcakes are decent, I suppose, for cupcakes. I tried the maple bacon, cookies and cream, red velvet with vanilla frosting, and some kind of chocolate explosion something-or-other. Kudos for incorporating bacon into baked goods, but at the end of the day, nothing was special enough to warrant the price. Too much frosting, and not enough emphasis on the cake.

The Pie

Minna: Cupcake craze, daze or whatever aside, the pie’s all right! While I can’t claim that every pie slice was a stunning burst of flavor, there are definitely some favorites on the menu. The classic apple pie is one of the best. The crisp texture of fresh apple slices and a scattering of nuts enhanced the baked blanket of buttery crust and cinnamon flavor; no mystery apple mush here! An impulsive decision to try the chocolate peanut butter slice, after the staff insisted it was great, made for a fun way to act like a kid. The overly sweet abundance of fresh whipped cream and the thick layer of chocolate sauce separating from the rather thick peanut butter crust reminded me of childlike days before the dentist’s scolding was a concern. Wielding a plastic fork and stabbing at the overly large crust made indulging in this heap of sugar a fun feat.

Caitlin: Hated it. We tried one slice of every single kind of pie offered in the shop on the day we went, which included classic apple, Dutch apple, sugar crème, key lime, and chocolate peanut butter. Slices are $3.50 a piece. Let’s get into it. There is nothing “classic” about the classic apple. The apples are undercooked, undersweetened, and the pie has more walnuts in the filling than apples. It should be called “walnut pie with a couple-a crunchy apples.” The Dutch apple’s topping was mushy and the apples were still undercooked. The sugar crème’s crust was good and flaky, but the filling is… well… gloopy. The key lime is not tart and not served cold enough. The chocolate peanut butter pie’s peanut butter crust is as rock hard as Chuck Norris’ abs; Minna and I comically stabbed at it with our plastic forks to no avail. I think we even broke a tine. Hilarious, but not edible.

My point is this. If you’re going to open a shop that specializes in one thing, like a pie shop, or a spy store, or bean bag emporium, you’d better bring your A-game on that one very specialized thing. Why would I visit a pie shop that had “just okay” pie? At $14 for a 6 inch pie, and $21 for a 9 inch pie, I would ask better of the Uptown Pie Company.

The New Seating
Minna: As a transitioning neighborhood, Uptown doesn’t have too many areas to lounge in the Wilson Yard area. The addition of this charming and quaint seating area makes for a great space to gather in this unique neighborhood. The wall art showcasing colorful cupcakes of creative toppings, made by Ms. Johnson’s 5th grade class of Beye Elementary, adds to the cheerful atmosphere of the new space. An added perk is the “Five Dolla Holla” deal, where you can enjoy a slice of pie and a cup of coffee while relaxing in this lounge for just $5.

Caitlin: Okay, the wall art by the kiddos is cute. It’s nice that they expanded the space so people can sit down to eat their cupcakes and pie slices. I’m just not convinced that the pie will motivate customers to keep coming back.

Uptown Pie Company is located at 1319 W Wilson Ave.