The Comprehensive Guide to Pittsburgh
You guys know that I live in Chicago, where I eat, drink, and support independent bookstores with every spare dollar I have. But I haven’t been here forever, and, as much as I love Chicago with my whole heart and stomach, I’m a Pittsburgher at heart and that’ll never change.
Since I graduated from college (CMU, also in Pittsburgh), I’ve grown an appreciation for the Steel City and all that it has to offer in terms of good eats and good reads. I get to go back regularly, and I’m excited to share the comprehensive guide to all of the places I try to visit when I’m back in the good old 4-1-2.
What to Eat
There’s so many things I want you to eat in Pittsburgh that I actually need to break it up into meals. Sorry. But not really.
Let’s get straight to it, starting with breakfast. Run, don’t walk, to Five Points Artisan Bakeshop in Squirrel Hill (my stomping ground for four years). Owner and baked goods enthusiast Geoff Comings is probably going to be there behind the counter, slinging loafs into his industrial bread ovens, listening to NPR, and bantering with his staff of Pittsburgh’s best bakers, most of whom have come to the bakery after stints at other shops around town and stayed put. The result is a menu that is unassuming and one hundred percent delicious. Last time I was in town, I hung out with them one morning as they prepped and felt like I wanted to stay forever (the pictures are from my too-short morning). The highlights here are just about everything (I and my waistline wish I was kidding), but I’d be lying if I told you I didn’t have favorites. Get a loaf of the raisin walnut bread (my dad is addicted), the sunflower and flaxseed loaf, and a tahini cookie. Hot. Damn.
After all those carbohydrates, you’re going to want a cup of coffee or seven. I have great news for you, and it’s that La Prima Espresso exists. I didn’t realize how lucky I was to have a La Prima coffee stand on campus until I started working in Chicago, which, as it turns out, is not walking distance from my all-time favorite coffee. They’ve been roasting coffee beans for THIRTY YEARS in Pittsburgh, and have one of the grittiest, cutest, most Italian joints ever in the Strip District. Not in Pittsburgh? Good news. They ship.
Bonus breakfast is tracking down some Fight Sized Doughnuts. I’m biased, but also they’re the best.
It’s really none of my business whether you eat at these places for brunch, lunch, or dinner, so you do you. Although rest assured, I’m making my preference clear. But really, up to you. Just make sure you go. Seriously. Without question.
Okay, first, have the brunch of your life at Enrico Cafe in the Strip District. I’m trying to summon the willpower to both accurately sum up what eating here is like while conveying how jealous I am that you’re going there. Whew. Alright. Picture a bakery that churns out famous biscotti. Now picture that bakery, but make it in the back of an alley strung with lights and hand-painted signs. Now picture that bakery but with a tiny wine bar, staffed by a woman known as the Wine Fairy (real thing), and maybe 15 tables that make the space cozier than your closet pre-Marie Kondo. That’s Enrico Cafe, and I can’t recommend it enough. Rustic, family-style Italian food comes to you seconds after it’s taken off the heat, you’re probably being served by the cousin of the owner, and oh yeah, everything is amazing. True story: once, the staff SET UP A FOLDING TABLE in the kitchen for me because they didn’t have room anywhere else. That’s the kind of thing that you remember seven years later.
Okay. On to our next stop: Gaucho Parrilla Argentina, also in the Strip District, but closer to Downtown. If a vegetarian recommends an Argentinan cafe known for its meaty sandwiches to you, you should go. Gaucho does not take reservations, they sell out fast, and you should probably already be there by the end of this sentence. Approachable but exciting, the menu features everything from sandwiches to steak plates and everything in between. Don’t miss the bread (sandwich, side, whatever, just eat it), and try to grab a seat on their tiny patio to watch the world pass you by. $5 says you see a self-driving Uber.
Let’s talk about the dinner program. You’ve got two options here and neither of them is a bad one. Do the whole Downtown thing with a dinner at The Commoner, located in the Kimpton Hotel Monaco. My sister and I took my parents there for dinner, and man, was it a great dinner. I was happy with everything we ordered, and that’s not something I say a lot about dinners out. Go for a cocktail while you’re in, and don’t skip dessert. If you’d rather keep things more casual, head over to Lawrenceville and hit up one of my all-time favorite places, The Vandal. The vibe! The wine list! The veg-forward creativity! Ugh, I’ve died.
What to Drink
In every city guide, they tell you that there’s a craft beer scene like no other in [insert place here]. I’m here to tell you that in Pittsburgh, you don’t have to stick to just beer. In fact, you should probably expand your horizons and drink all of the drinks. Case in point: Hidden Harbor, where I hung out with co-owner Adam Henry, who’s probably one of the coolest people I’ve ever met. I mean, the guy knows more about tiki bars than I know about any kind of bars. This is epic. So is the tiki bar he and his business partner created after their underground tiki nights became too popular not to share with the general public. Adam and company did an incredible amount of research before opening Hidden Harbor and it shows. The cocktails, the glassware, the decor, the music, and the flowers in the drinks are all so thoughtfully selected that by the time your over-the-top tropical bev lands in front of you, you’ve already convinced yourself to stay for another drink.
Bonus? They have a James Beard-nominated team cranking food out from the kitchen in the basement. Extra bonus? They’re next door neighbors to Independent Brewing Company, the one-stop-shop for all of Pittsburgh’s favorite drinks. Extra extra bonus? This team just opened a third concept, Lorelei, that’s rumored to be amazing. I might stop there before I even get home next time I’m in town.
If you’re trying to focus exclusively on spirits, head back down to the Strip District and take a tour at the James Beard Award-nominated Wigle Whiskey. Besides just the tastiest whiskey (and I don’t like whiskey) and other spirits, you also get a nice dose of Western Pennsylvania history. Also, a tasting flight. Also, some of the best cocktails I’ve ever had.
Not into liquor? No worries. Brew Gentlemen, up in Braddock, is a little out of your way but well worth your while. They have a line-up of some of my favorite beers ever, a host of food trucks, and an origin story near and dear to my heart.
What to Book
Pittsburgh has an awesome selection of tiny shops that most likely also sell books, so don’t feel limited by the round-up of my top three. Chances are, if you walk in and start chatting, the person behind the counter will have a recommendation for where to stop next.
The bookstore where I spent the most time (and money) while in school was Caliban Book Shop. It’s a winding, classic old book store with an awesome selection of art books, Pittsburgh writers, and those wonderful ancient editions of books you only find at stores like this.
For a little more of a mainstream vibe, make your way 20 minutes up the road to the Shadyside neighborhood to Kards Unlimited. I’m sure I’ll get flak for including this in a list of bookstores when it’s primarily recognized as a gift store, but I’ve found (and purchased) many a book there, including some novels and cookbooks that have traveled with me all the way to Chicago. Also, my blog, my rules. ¯\_(ツ)_/¯
The last place I’ll recommend is the place you’ll spend the most time. Located in a sleepier stretch of Lawrenceville down the street from The Vandal, The Big Idea Bookstore ticks all of my boxes: it’s a non-profit, it’s charming AF, and it has a cafe attached to it. Win, win, win. You’re welcome. Bonus here is that they probably stock Two Sides, Three Rivers, which as you know was written by one of my professors.
The Last Word
Though titled such, this is by no means the comprehensive guide to Pittsburgh. That town has more places to discover and fall in love with every day, and I personally can’t wait to go back soon and keep doing just that. If I missed your favorite thing or you want to argue with me about why I didn’t include Pamela’s for breakfast, leave a comment below or send me a note at email@example.com.