Hip, hilly, and friendly, Pittsburgh rewards curiosity. This western Pennsylvania city is home to cool museums, great architecture, and a food scene that’s a mash-up of Asian, Eastern European, vegan, dinette, and haute cuisine. Located at the meeting point of three rivers, you can crisscross its dozens of scenic bridges to see the city from all its vantage points.
Day 1: Morning
10 a.m. Drop your bags at the spankin’ new Tryp by Wyndham in Lawrenceville. The former industrial trade school is located in the perfect neighborhood for a non-stop weekend. Another plus: it’s three minutes from downtown Pittsburgh and 30 minutes from Pittsburgh International Airport. Sneak a peek at the hotel’s artwork, all by the city’s contemporary artists, and drop off your stuff. Then shift into cruise mode: the easiest introduction to the city is on its rivers.
Take a bike share, Scoobi, or Uber downtown to the Gateway Clipper dock. (Along the way you’ll notice dozens of sleek, slow cars with spinning LIDAR helmets. They’re a piece of the city’s new role as a leader in robotics and autonomous vehicles.) This fleet not only ferries fans to the Pirate and Steeler stadiums downtown, but it also offers sightseeing cruises year-round. The rivers are the easiest place to view the city’s past and present. The sternwheeler chugs through a landscape famously built by steel. Today there’s not a single mill within city limits, and the skies are clear. The reclaimed riverbank trails attract bikers and joggers year-round, and in warm weather, you can rent a kayak from Kayak Pittsburgh to explore the waters yourself.
12 p.m. After your cruise, wander down East Carson Street, and don't forget to look up. The century-old buildings here are named for the ethnic clubs and churches of many generations of immigrant steelworkers. Stop for a craft ale or Scotch egg at Piper’s Pub and its Pub Chip Shop, a friendly Brit-style bar and cafe. Grab a high-top in the window at Nakama for upscale sashimi and nigiri. Can’t make up your mind? Choose from the global menu at Streets on Carson. Choose cheap tasty portions of fried polenta from Puglia, aloo tikki from Islamabad, or pork egg rolls from Shanghai, all from chef Matt Christie.
Day 1: Afternoon
2 p.m. Make a stop at the park downtown where the Monongahela and Allegheny Rivers meet to form the Ohio—the confluence is marked with a mighty fountain in Point State Park. Then, cross the Clemente Bridge for an immersion in contemporary art at two North Shore museums. First, visit the Mattress Factory. This museum of installation art name-checks the world’s leading artists in its permanent collection: James Turrell’s creations in light, Yayoi Kusama’s infinity rooms, and Greer Lankton’s “It’s All About ME Not You,” the final fantastic installation by the LGBT artist.
4 p.m. Another LGBT icon is waiting a half-mile away. Grab a ride to the Andy Warhol Museum. The King of Pop Art was born and raised in Pittsburgh, and the massive exhibits and archives of his work fill an ornate seven-story building just steps from the Andy Warhol Bridge. The Warhol is the reason to make sure you spend a Friday evening in Pittsburgh: the museum stays open until 10 p.m. for First Fridays. Programs may include Warhol films or live music performances by international acts in the theater, cocktails at the lobby bar, and exhibits by artists influenced by Warhol, like Ai Wei Wei. Make sure you feed a few quarters into the arcade-style strip-photo booth, too. And finally, do exit through the gift shop. The funky collection of objects inspired by Warhol will provide souvenirs—or tongue-in-cheek birthday gifts—for everyone you know.
Day 1: Evening
8 p.m. Head back to Lawrenceville to refresh for the evening. Along Butler Street, dining options abound. The Vandal is a tiny storefront with big flavors. Try the potato latkes and Eastern European specials. The Abbey, a former funeral home that’s livelier than its past, sits across the street from the entrance to Allegheny Cemetery, a historic, bucolic park that’s worth a wander. The Abbey's patio, with a fountain and a sidewalk view, offers great people-watching. Near the other entrance to the cemetery, on Penn Avenue, is Apteka, a vegan bistro; step up to the bar for craft cocktails. Next, stroll to 51st Street for two levels of dancing and fun at Spirit (motto: Booze. Pizza. Party. PGH). It’s Lawrenceville’s favorite casual clubhouse in an old Fraternal Order of Moose lodge. Close out the evening back at the Tryp’s rooftop bar, OverEden.
Day 2: Morning
10 a.m. Begin your day with brunch in the Strip District. Unlike the Vegas version, this Strip is a century-old brick and cobblestoned wholesale market—loud, friendly, and bustling, especially on Saturdays. Grab a bite to eat on 18th Street; Pamela’s P&G Diner and Smallman Galley are popular choices. If you’re a fan of the classic breakfast-all-day, hash-browns-and-pancake diner menu, you can’t beat Pamela’s. If you want lots of options, try the Galley. This bar and dining room allows a rotation of young chefs to test their chops at small stations. Step up to order and pay, and they’ll serve you at your table. Walk it off with a food-centric stroll along Penn Avenue. The fresh Atomic Pepperoni rolls at Sunseri’s, a world of cheeses at Penn Mac, and Lebanese deli treats at Labad’s Cafe and Grocery are all worthy take-aways.
12:30 p.m. In Millvale, a borough two miles from the Strip, visit St. Nicholas Croatian Catholic Church for the stupendous Vanka Murals. Croatian artist Maxo Vanko created the brutal, unearthly, and socialist frescos of workers and soldiers on the church’s ceiling during two visits in the World War II era. Recently refurbished and restored, they’re spotlit during guided tours on Saturdays. Don’t be surprised if your tour guide is a lifelong member of the parish with memories of the artist himself.
Day 2: Afternoon
3 p.m. Take a break at The Grist House, a short walk down the hill. As craft breweries have exploded in the Burgh, Grist House beers get respect at plenty of local bars. But only the brand’s mothership pours them in a huge, sunny beer garden with food trucks on the side. Expect lots of dogs and several rounds of Cornhole.
6 p.m. Chef Bill Fuller’s reputation for creating five-star restaurants around Pittsburgh is legendary. Eleven, Casbah, and Soba are well worth a visit. But his latest opening is getting raves, too. Alta Via doesn’t dazzle on the outside, in a strip mall in suburban Fox Chapel. But the intimate, beautifully designed interior may be the most relaxing space in town. Don’t rely on the modern Mediterranean menu choices—make sure to hear about the half-dozen farm-to-table options and luscious pastas that are frequent specials.
Day 2: Evening
9 p.m. The Burgh puts the fun in funicular. The historic cable cars climbing Mount Washington, the ones you see on the postcards, are part of the city transit system and a bargain ticket at $3.50 per round trip. A good circuit is to board the Monongahela Incline at the bottom at Station Square. Take the five-minute ride up the steep cliff, 367 feet high. Stroll Grandview Avenue to the Duquesne Incline to savor the view of the Point as the moon rises behind downtown’s skyscrapers, then hop aboard for the descent.
12 a.m. Hot Mass is not for the faint-hearted. Held Saturdays beginning at midnight, this downtown EDM and techno party alternates guest DJs weekly and raves on until 8 a.m. Dance till you drop: when you get back to the Tryp, you can recover with a good night's rest.