“What I love most about Pittsburgh is the friendliness of the people,” mentions Brooke Barker, the creator of the charming newsletter Never Not Nervous. “On our first visit, a runner stopped to help us with directions because we appeared lost.” Brooke and her spouse, Boaz, moved to Pittsburgh in 2019 and now explore the city with their young son and pet. Here, Brooke reveals a magical park, her top bookstore, and where to enjoy pierogis…
Our amazing guide
WHERE TO EAT
APTEKA
Pierogis have a significant presence in Pittsburgh. APTEKA serves vegan Central and Eastern European cuisine. Arrive half an hour before opening to secure a table for the first seating. Try the fried pierogis. S&D Polish Deli is a lively spot for pierogis in the Strip District. You can also enjoy pierogis at Pittsburgh Pirates games, while watching pierogi mascots race each other between innings.
Penn Avenue Fish Company offers excellent fish sandwiches. The lively setting resembles a fish market more than a restaurant — partly because it doubles as one.
Dad’s Dog & Burger
Dad’s Dog & Burger is quite adorable and budget-friendly. It’s relatively new, and I want to establish a personal ritual of ordering hashbrowns and maybe reading the newspaper.
Brooke’s spouse and child at Hidden Harbor
I adore tiki bars, and Hidden Harbor is particularly enjoyable. The menu accommodates various dietary needs, with drinks served in a flaming skull. They organize classes on tiki bar history and pop-up events showcasing a famous 1970s drink.
Leona’s is a local ice cream sandwich business with seasonal flavors in tasty combinations. (My favorite is black sesame with tahini cookies.) They’re also available at local grocery stores and numerous local bars.
WHERE TO HANG
Children love the Duquesne Incline, but I take friends of all ages. The ride is short yet scenic, with a museum and observation point at the summit.
Liberty Magic is a wonderful intimate magic theater. Magicians come from all over the globe to perform. We bring every visiting friend, and for 90 minutes, I genuinely believe, ‘This person could be magical.’
I enjoy the August Wilson African American Cultural Center and the Andy Warhol Museum. There’s also the Troy Hill Art Houses where global artists are given a whole house to create freely. Sign up for complimentary guided tours. I won’t reveal too much to avoid spoiling the surprise, but wear something you can move comfortably in!
Frick Park looking idyllic
Spanning 644 acres, Frick Park is like a vast forest within the city. It’s a beautiful, tranquil place for a walk, provided it’s not during winter. (Pittsburgh winters can be extremely chilly, dreary, and prone to fierce storms.) The park offers wooden pathways, a playground, and a lawn bowling green — lawn bowling there is on my Pittsburgh to-do list!
Phipps
For unpleasant weather, a brilliant destination is Phipps Conservatory & Botanical Garden. It’s extensive, lush, and most importantly, indoors.
Frank Lloyd Wright’s Fallingwater home is a quick day trip from the city and truly worth visiting. I never considered myself an architecture enthusiast, but it entirely changed my perspective on the connection between environments and oneself.
WHERE TO SHOP
White Whale Bookstore
White Whale Bookstore is among my favorite Pittsburgh spots. The independent bookstore hosts a café and bar, providing a space to read or socialize. They allowed me to paint a mural in the children’s section, which you can view during your visit.
Vendor Bender operates 24/7 with vending machines offering global snacks.
Pittsburgh Center for Creative Reuse is a non-profit arts supply store packed with donated items like yarn, fabric, and craft materials galore. Purchase doll hands, search through button bins, and get the precise elastic length you need. Construction Junction is similar, but focuses on architectural salvage, vintage arcade games, and theater seating. It’s all there! (Though I realized I might have more interest in odd doors, scrap items, and an assortment of 50 toilets than the average person.)
Love, Pittsburgh
The Strip once served as a wholesale supply hub for restaurants, but now it’s renowned for great shops and dining. For souvenirs, check out Steel City, a local clothing brand, or Love, Pittsburgh, showcasing work from 100 different local creators.
WHERE TO STAY
Pittsburgh comprises 90 neighborhoods, each unique in character and community. Some say each neighborhood is so dedicated to its own pizzeria that during citywide pizza polls, national chains triumph because votes are divided 90 ways.
TRYP Hotel occupies a former trade school.
Consider staying in Lawrenceville or Mexican War Streets. In Lawrenceville, the TRYP Pittsburgh Hotel is an excellent choice. If you rent a VRBO in Mexican War Streets, it’s a stroll away from the Mattress Factory (a modern art museum), ShadoBeni (a top-notch vegan eatery), and Happy Day Dessert Factory (an ice cream shop).
Editor’s note: Joanna cherished her stay at The Inn on Negley while visiting her cousin in Shadyside; and Pittsburgh Magazine awarded the Priory “best boutique hotel” last year.
FINAL TIP
Most fun is had if you rent a car. I wish getting around without a car was easier, but the city isn’t quite there yet.
Thank you for offering such enjoyable suggestions, Brooke! And Pittsburgh locals, what else would you include?
P.S. Explore more Cup of Jo city guides, and the oddest, best elements of trips.
(Top photo by Heng Yu/Stocksy. Personal photos courtesy of Brooke.)
