Second City Sojourns: An Art-Themed Long Weekend in Pittsburgh, PA

Randyland

In 1995, Randy Gibson had a credit card with a $10,000 limit and a dream. He purchased a few houses in the North Side and turned them into Randyland, an art installation and garden that resembles Willy Wonka’s Chocolate Factory if Wonka had taken a bunch of psychedelics. Entry is free, although weather-dependent. Plan to spend at least an hour examining every square inch.

The Andy Warhol Museum

Most artists may get their 20 minutes of fame, but it’s safe to say public fascination with Andy Warhol is timeless. The Andy Warhol Museum houses the largest collection of the artist's work and archival materials and walks visitors through every aspect of Warhol’s life; if you’re a pop-art fan, this one’s for you.

Mattress Factory

This contemporary art museum sets itself apart with its “artist-centered” designation, with most of the exhibits the result of intensive artist residencies hosted by the museum. Creators are invited to stay in Pittsburgh and create something new to be exhibited at the Mattress Factory. Exhibits are frequently immersive and experimental; leave your expectations of what it means to be a visitor at the door.

Heinz History Center

Pennsylvania’s largest history museum is a love letter to Western Pennsylvania’s history and people. Exhibitions are interactive and bring out the kid in all of us.

Nationality Rooms

One of the most unique things Pittsburgh has to offer! Housed in the Cathedral of Learning on the University of Pittsburgh campus, the Nationality Rooms are a collection of 31 classrooms that are authentically decorated and designed to represent the various ethnic groups represented in Pittsburgh. Guided tours are offered throughout the week and can be booked through the university website.

Duquesne Incline

Pittsburgh is a city of hills, and the best way to climb them (and take in the incredible panoramic views offered at the top) is to take a ride on one of the two inclines—funicular railways designed to transport people and cargo up the steepest of slopes. Rides are $2.50 each way and operate every five minutes. Make sure to give yourself ample time at the top to enjoy the incredible Pittsburgh skyline.

Point State Park

Located at the junction of three rivers (at the tip of Pittsburgh’s “Golden Triangle”) is a 36-acre urban oasis where visitors can enjoy walking and biking trails. An iconic fountain right on the water, which shoots water 150 feet into the air, has become a famous symbol of the city; stop by and see it for yourself.

Shop the Strip District

This half-mile district, which abuts downtown, was once an industrial corridor but is now filled with amazing restaurants, international grocery stores, and lots of unique shops. Give yourself plenty of time to explore every nook and cranny of this gem.

350 Degree Bakery

A small-batch bakery open Thursday–Sunday, famous for its biscuit sandwiches and cinnamon rolls. Order a savory treat to start your morning, but make sure to get a sweet one to go—you’ll be glad you did!

De Fer Coffee and Tea

Although there are several locations throughout Pittsburgh, the flagship shop in the Strip District tends to be a fan favorite. Hand-roasted beans and homemade syrups add an artisanal touch to a solid cup of coffee. Make sure to grab one before you go shopping.

Prantl’s

A Pittsburgh institution for over 50 years, this bakery is nationally recognized for its Burnt Almond Torte. In 2014, The Huffington Post dubbed the torte—layers of yellow cake cemented with vanilla custard and covered in buttercream and toasted candied almonds—“The Greatest Cake America Has Ever Made.” Stop in and see for yourself.

DiAnoia's Eatery

Located in the thriving Strip District, DiAnoia’s, with its whitewashed walls and pops of blue, is reminiscent of a classic Italian beachside café. While any meal there is delicious, Sunday brunch (complete with a zeppole) is where it really shines.

Chengdu Gourmet

While the standard Chinese-American fare at Chengdu Gourmet is plenty delicious, the Sichuan specialties are where this restaurant really shines. Portions are family-style, and the menu is sizable—bring a large group so you can sample a wide variety.

Apteka

An all-vegan Eastern European menu that wins its chefs James Beard nominations? You better believe it. After a decade of existence, Apteka has proven vegetables can stand on their own. The menu rotates often based on seasonally available ingredients, and reservations for groups of four or more are recommended.