A ONE-TIME steel boom town, Pittsburgh is now famous for being a tech hotbed; home to two major universities (Carnegie Mellon and the University of Pittsburgh); and many exciting activities to keep visitors and residents occupied every night of the week.
Where to stay
Not Another Hostel
The cheapest and most welcoming place is Not Another Hostel in Regent Square. This donation-based hostel and private homeless shelter (each functioning in different buildings) is someone’s house and is opened to passing travelers. Jon and his doggie friends Luther and Beau will welcome guests (with pre-arranged bookings) to sleep in one of the hammocks or air mattresses scattered around the joint.
Address: Exact address given at booking Price range: By donation
The Priory Hotel
If you’re looking for slightly more upscale venues, try The Priory Hotel. The Priory used to be a Benedictine monastery and has all the amenities you’d expect from a modern hotel, with gorgeous old stonework and views of the Allegheny River, as well as wine parties and other social events on the premises.
Address: 614 Pressley Street Price range: $99 to $250 (depends on time of year, size of room, and day of the week)
The Shadyside Inn
The Shadyside Inn is in the upscale neighborhood of Shadyside, close to boutique shops and restaurants, and walking distance to one of our favorite eating spots, the Harris Grill (see below). They have free cookies at check-in, free bikes to borrow, and an on-site dog park.
Address: 5405 Fifth Avenue Price range: $150-$280 (depends on time of year, size of room, and day of the week)
The Morning Glory Inn
The Morning Glory Inn is a Victorian-style bed and breakfast in the South Side (which means close to a lot of night life). Every room is unique, and they also offer suites if you’re feeling fancy; some have full stone fireplaces and claw-foot tubs. The central courtyard is lit by candles at night.
The Harris Grill is a welcoming, casual restaurant with friendly staff and seasonal cocktails. It’s summer now, so they’re offering a Blueberry Basil Lemonade that makes me feel refreshed just reading the ingredient list. You can also show your appreciation by buying the staff a round for $10 — after which we guarantee you will get the very best bacon appetizers they offer.
Address: 5747 Ellsworth Ave. Hours of operation: Mon-Fri 11:30 AM – 2 AM; Sat and Sun 11:00 AM – 2 AM
Double Wide Grill
Back over on the South Side, the Double Wide Grill is a sports bar with a plentiful vegan menu, so you can watch the Steelers AND have seitan chicken wings.
Address: 2339 East Carson St. Hours of operation: 11 AM-11 PM, more or less
Zenith Vegetarian Cafe and Art Gallery
If you prefer a quieter brunch without the big-screen televisions, go to Zenith Vegetarian Cafe and Art Gallery. Eclectically-decorated, the restaurant also hosts an antique shop that is a treasure trove of genuine items. They change their menu every week, so check online to see what you’re getting.
Address: 86 S. 26th Street Hours of operation: Thursday-Saturday 11:30 AM – 8:30pm; Sunday (brunch) 11 AM – 2:30 PM
Beehive
If you want a coffee, sandwich, or liquor milkshake, hit up the Beehive, also on the South Side. This has long been my favorite cafe, and it’s an old one, founded in 1991.
Address: 1327 East Carson Street Hours of operation: Sun and Mon 8 AM – 11 PM; Tues, Wed, and Thurs: 8 AM – 12 AM; Fri and Sat: 8 AM – 2 AM
Dave and Andy’s
If you prefer just the ice cream part of that milkshake, head to Dave and Andy’s, probably the best homemade ice cream shop I’ve ever been to. The birthday cake ice cream is one of their most popular, but you never know what you’re going to get, as their menu changes daily.
Address: 207 Atwood St Hours of operation: 11:30 AM – 10 PM
For late night/early morning cravings:
Finally, if you’re up late (or very early), and you want some good old classic diner food, consider one of the following: the O (Essie’s Original Hot Dog Shop), Pamela’s, or the classic of local all-nighters, Eat‘n’Park. The O is in student-neighborhood Oakland, and has the greasiest and most delicious fries available until 1:30 AM. Pamela’s opens at 7 AM and is the go-to for pancakes. Eat’n’Park is pretty standard American diner food, but they’re open until 3 AM (or sometimes 24 hours), and serve a tantalizing snack called Grilled Stickies: like a pecan pie, cinnamon roll, and French toast all in one. Try a Smiley Cookie on your way out.
If you’re looking for a daytime good time, go to Randyland, Pittsburgh’s most colorful landmark, in the Mexican War Streets of the North Side. Owner Randy Gilson has been expanding his home into a creative interactive artwork since 1995 and welcomes visitors for free most days. Also on the North Side is The Mattress Factory, a contemporary art museum and event space in an old mattress warehouse that was built in 1900. Home to community art labs, classes for kids, and evening openings and parties, there is always something interesting happening.
Randyland
Address: 1501 Arch Street Hours of operation: 10 AM – 5:30 PM, most days
The Mattress Factory
Address: 505 Jacksonia St Hours of operation: Tuesday-Saturday: 10 AM – 5 PM; Sunday: 1 PM – 5 PM
Across the river in the Cultural District, visit Arcade Comedy Theater for nightly comedy shows. My favorite is Knights of the Arcade, a D&D improv comedy show of epic tale-telling and role-playing where the audience directs the action. You might be thinking “I wish I could go bowling while I listen to music and dance,” in which case, Arsenal Lanes is for you. Live bands, DJs, bowling, and cocktails are all together in Lawrenceville for an unforgettable fun time.
Arcade Comedy Theater
Address: 811 Liberty Avenue Hours of operation: Fridays and Saturdays 7:30 – 11:30 PM; Sundays from 6:30 – 9:30 PM
Arsenal Lanes
Address: 4310 Butler St. Hours of operation: Monday-Thursday: 12 PM – 12 AM; Friday: 12 PM – 2:00 am; Saturday: 11:00 AM – 2:00 AM; Sunday: 11:00 AM – 12 AM
You can participate in the self-directed “South Side Crawl” by wandering down Carson Street anytime after 9 PM and stopping at a selection of bars along the way. Possibly, you’ll pass by The Rex Theater during a showing of local performing artists Squonk Opera’s latest offering…or you’d prefer the All-Metal Beegee’s Tribute. Either way, The Rex has what you didn’t even know you needed.
The Rex Theater
Address: 1602 E. Carson St. Hours of operation: Dependent on the show, box office opens a half-hour beforehand
