“My favorite thing about Pittsburgh is how friendly people are,” says Brooke Barker, the author and illustrator behind the delightful newsletter Never Not Nervous. “The first time we visited, a runner ran across the street to give us directions because he thought we looked confused.” Brooke and her husband, Boaz, relocated to Pittsburgh in 2019 and now explore the city with their toddler son and dog. Here, Brooke shares a magical park, her favorite bookstore, and where to eat pierogis…

Our wonderful guide

WHERE TO EAT

APTEKA

Pierogis are a big deal in Pittsburgh. APTEKA makes vegan Central and Eastern European food. Go half an hour before they open and wait in line to get a table at the first seating. Order the fried pierogis. S&D Polish Deli is a fun place to get pierogis if you’re in the Strip District. You can also get pierogis at Pittsburgh Pirates games, and eat them while you watch the pierogi mascots race each other between innings.

Penn Avenue Fish Company has great fish sandwiches. The fun atmosphere feels more like a fish market than a restaurant — partly because it is also a fish market.

Dad’s Dog & Burger

Dad’s Dog & Burger is very cute and reasonably priced. It’s new-ish, and I want to start a personal tradition where I get hashbrowns and, I don’t know, read the newspaper or something.

Brooke’s husband and baby at Hidden Harbor

I love all tiki bars, but Hidden Harbor is especially good. The menu has lots of options for different dietary preferences, and you can drink something in a flaming skull. They host classes about the history of tiki bars and pop-up nights where they make a drink that was famous in the 1970s.

Leona’s is a local ice cream sandwich company with seasonal flavors in delicious combinations. (My favorite is black sesame ice cream with tahini cookies.) They also sell them at local grocery stores and lots of local bars.

WHERE TO HANG

Kids love the Duquesne Incline, but I take friends of any ages. It’s a short but very scenic round trip ride, and you’ll find a museum and lookout point at the top.

Liberty Magic is an amazing small magic theater. Magicians come from around the world to perform. We take every friend who comes to town, and for an hour and a half, I always think, ‘This person might actually be magic.’

I like the August Wilson African American Cultural Center and the Andy Warhol Museum. Then there’s the Troy Hill Art Houses where artists from around the world are given an entire house to create whatever they want. Sign up for free guided tours. I don’t want to say too much because I don’t want to spoil it, but wear something you can crawl around in!

Frick Park looking dreamy

With 644 acres, Frick Park is like a full-on forest in the middle of the city. It’s a beautiful, peaceful place to walk around, as long as it’s not winter. (Pittsburgh winters can be super cold, gray, and prone to terrible thunderstorms.) The park has wooden trails, a playground, and a lawn bowling green — going lawn bowling there is on my Pittsburgh bucket list!

Phipps

During bad weather, a perfect place to go is Phipps Conservatory & Botanical Garden. It’s huge and lush and, best of all, indoors.

Frank Lloyd Wright’s Fallingwater house is a quick day trip outside of the city, and you definitely should go. I’ve never thought of myself as a huge architecture person, but it completely changed the way I think about the relationship between my surroundings and myself.

WHERE TO SHOP

White Whale Bookstore

White Whale Bookstore is one of my favorite places in Pittsburgh. The independent bookstore has a café and a bar, so you can sit down and read or meet up with friends. They let me paint a mural in the kids section, so you can check that out while you’re there.

Vendor Bender is a 24/7 shop with working vending machines full of snacks around the world.

Pittsburgh Center for Creative Reuse is a non-profit art supply shop filled with donated materials, including yarn, fabric, and any sort of craft stuff you can imagine. You can buy doll hands, sort through bins of buttons, and get the exact length of elastic you want. Construction Junction is similar, but for architectural salvage, old arcade games, and theater seats. It’s all there! (But I realized I might be more interested in random doors, scrap objects, and a collection of 50 toilets than the average person.)

Love, Pittsburgh

The Strip used to be where restaurants picked up their wholesale supplies, but now it’s a neighborhood known for great shops and restaurants. For souvenirs, try Steel City, a Pittsburgh-based clothing brand, or Love, Pittsburgh, which has work from 100 different local artists and makers.

WHERE TO STAY

Pittsburgh has 90 neighborhoods, each with its own character and community. People say that every neighborhood is so loyal to its own pizza place that when there are citywide pizza rankings the national chains always win, since most of the votes are split 90 ways.

TRYP Hotel is in a former vocational school.

Two neighborhoods to stay in: Lawrenceville or Mexican War Streets. In Lawrenceville, TRYP Pittsburgh Hotel is a great spot. If you rent a VRBO in Mexican War Streets, you’re walking distance to the Mattress Factory (a contemporary art museum), ShadoBeni (a great vegan restaurant), and Happy Day Dessert Factory (ice cream shop).

Editor’s note: Joanna loved staying at The Inn on Negley when visiting her cousin in the Shadyside neighborhood; and Pittsburgh Magazine named the Priory the “best boutique hotel” last year.

FINAL TIP

You’ll have the most fun if you rent a car. I wish it were easier to get around without a car, but we’re not there yet.

Thanks so much for sharing such fun ideas, Brooke! And Pittsburgh readers, what would you add?

P.S. More Cup of Jo city guides, and the weirdest best part of trips.

(Top photo by Heng Yu/Stocksy. Personal photos courtesy of Brooke.)