Travel
5 min

A budding love for Pittsburgh

Exploring Pittsburgh Pride, from open bars to stunning skyline views

Picturesque Pittsburgh as seen from Mount Washington. Credit: Perry Planet

When my editor tells me to “take it all in” while covering Pittsburgh Pride, I do exactly that, from open bars to stunning skyline views. But while I try my best, a four-day visit isn’t long enough to experience everything the charming city offers.

Thursday: Wet and wild on Mount Washington

A delayed flight and too many episodes of Orange Is the New Black for one sitting induce complete exhaustion. I make it to Pittsburgh and drag my bags out of the airport just before 10pm. But there’s no time to rest: I have just enough time to stop at my hotel, slip into my swim trunks and head to Splash, an annual Pride pool party and the first event on my schedule.

Every year, Steve Herforth and Peter Karlovich host the party at their lavish home in the Mount Washington neighbourhood, which was rated the second most beautiful (and best urban) vista in America by USA Weekend. An infinity pool and hot tub overlook the city, and an open bar that won’t run dry fuels the rowdy crowd. Shirts do not exist at this party; prepare to be scolded if you opt to keep yours on.

The party is overflowing with friendly people. A nice Pittsburgh native promises to be my personal tour guide in the morning, so I split and get some beauty rest just as the tequila shots off naked men begin.

Friday: Returning to the scene before nightfall

I wake up at the Hampton Inn in the middle of the Strip District downtown. No, not where all the strippers make their cash — it’s a cultural strip of land between a large hill and one of Pittsburgh’s three lakes. Foodies should head here to sample ethnic cuisine at very affordable prices.

Steps away is downtown Pittsburgh, with its welcoming vibe and thriving Cultural District. Known colloquially as the “Golden Triangle” because it’s located at the meeting point of the city’s three rivers, two of which border the downtown, it’s the city’s fastest-growing neighbourhood, thanks to a recent $7 billion investment. Other must-see areas include South Side, North Shore, Lawrenceville, East Liberty, Oakland, Shadyside, Sewickley and Monroeville.

After exploring by foot, my friend from the pool party pulls through and picks me up for a day of tourism. We head back to Mount Washington to take in its famous view in the daylight. Below we see the three rivers — the Monongahela and Allegheny, which meet to form the Ohio — laced with some of the city’s 446 bridges; hence the nickname City of Bridges. (Pittsburgh is also known as the Steel City, but it’s become less industrial in recent years.)

If you want to combine sightseeing with good food, hit the LeMont, an award-winning restaurant on Mount Washington. If the romantic setting doesn’t outweigh the pricey menu, don’t worry: there are plenty of smaller, more affordable restaurants nearby. My friend and I settle for Shiloh Grill, which will kill your diet; it’s incredible how much cheese they pile into a chicken quesadilla.

Don’t bother burning calories by walking; instead, take advantage of Pittsburgh’s famous funicular railroads, known as inclines. Of a dozen or so that were built in the 1800s, only the Duquesne and Monongahela remain. Both offer gorgeous views of the city as they transport you from Mount Washington to the Monongahela River.

After a brief nap, the evening is dedicated to the Pride pub crawl, a chauffeured tour of more than 13 LGBT-friendly bars, pubs and restaurants around town. Liberty Avenue downtown and Ellsworth Avenue in Shadyside have the most to offer, from local dives to crowded dancefloors. (Don’t be disappointed if you’re looking for the bars seen in the American version of Queer as Folk, which was set in Pittsburgh; the show was actually filmed in Toronto.)

Things do get filmed in Pittsburgh, though. Since the passage of the Pennsylvania Film Production Tax Credit in 2006, the city’s film industry has flourished. On my way back to my hotel, the cab driver fills me in on everything that’s been shot in Pittsburgh. Most notable are the Gotham City scenes from The Dark Knight Rises or almost any of George A Romero’s films. Sienna Miller got it all wrong when she told Rolling Stone she was stuck in “Shitsburgh” when filming The Mysteries of Pittsburgh, but she gives an incredible portrayal of Edie Sedgwick in Factory Girl, a biographical film about Pittsburgh-born Andy Warhol’s troubled star.

Saturday: Getting lost in crowded places

Warhol fans can walk across the Andy Warhol Bridge, one of three yellow bridges crossing the Allegheny River, and visit the Andy Warhol Museum. There are seven storeys, proving just how much of a hoarder Warhol was. But I don’t blame him. My entire Saturday afternoon is spent wandering around the building and gawking at such sights as a room full of floating silver clouds.

The Andy Warhol Museum is one of four Carnegie museums in the city. The others are the Carnegie Museum of Art, the Carnegie Museum of Natural History and the Carnegie Science Center. Pittsburgh is filled with museums. Other popular options include the Senator John Heinz History Center, the Children’s Museum of Pittsburgh, the Phipps Conservatory, Mattress Factory museum of contemporary art and the ToonSeum museum of cartoon arts.

Liberty Street is blocked off by Saturday night for the annual street fest, featuring headliner Chaka Khan, Canadian singer/songwriter Vita Chambers, American Idol’s Lazaro Arbos and Jordanian singer Ayah Marar. The street fest is fun, but it’s nothing compared to Toronto’s Church Street festival. And it isn’t free: it’s $40 in advance, $50 at the doors, and those who want VIP access to an indoor area and open bar pay $80. I stumble across the Kitty Pryde Fest VIP lounge, in the ToonSeum, where I pay $25 for access to an indoor lounge, washroom and another open bar.

While milking my newfound privileges, I make a few friends who take me bar hopping after the street fest closes. We indulge completely and it’s great.

Sunday: A budding love for Pittsburgh

Pittsburgh is buzzing with positive energy on Pride Sunday. They have all the reason to celebrate, since Pennsylvania legalized same-sex marriage in May. The march starts at the corner of Grant Street and the Boulevard of the Allies, then moves through downtown, ending at a free daytime version of the Liberty Avenue street fest. One of my new friends says it’s the best turnout he’s seen in the five years he’s attended.

Dance groups, drag kings and queens, alternative rock group Betty and “All American Boy” sensation Steve Grand perform onstage throughout the day. There are more than 150 vendors, a children’s area and a beer garden.

Before leaving, I decide to squeeze in one more attraction to feel like I’ve optimized my time. It’s quite a shift from the Pride parade, but I hit the Phipps Conservatory’s botanical gardens in Oakland. It’s beautiful and relaxing — the perfect end to a trip full of Pride celebrations.

Outside of Pride week, Pittsburgh isn’t necessarily a place to visit if you’re looking to party, but it’s charming and quaint and full of museums to get lost in. By the time I leave, it has become apparent why it’s considered one of America’s most livable cities by Places Rated Almanac, Forbes and The Economist.

For the most up-to-date travel information on gay Pittsburgh, see our City GuideListings GuideEvents Guide and Activities Guide.

For more information about Pittsburgh, go to visitpittsburgh.com.