Most of Pittsburgh’s bigger hotels are located Downtown, but if I had just 24 hours in the city, I’d stay somewhere in Oakland. That’s Pittsburgh’s university district, and it’s also the perfect base from which to explore the artsy and student-friendly East End. Spend the day people-watching, window shopping and strolling through the streets of Oakland, and then do more of the same in Squirrel Hill, which sits just ten minutes away by bus. If the weather’s nice, check out Oakland’s massive Schenley Park. If it’s cold outside or raining, explore the Nationality Rooms inside the University of Pittsburgh’s Cathedral of Learning, and then cross the street for a visit to the Carnegie Museum of Art, or the Carnegie Museum of Natural History. After the sun sets, hop in a cab (or a 54-C bus) to South Side’s East Carson Street for dinner–the range of eateries along this strip is impressively wide. On weekend nights, East Carson turns into one long bar-hopping party, so join the fun at a classic dive like Dee’s Café, a frat bar like Jack’s, or even the tiki-themed Lava Lounge.
Pamela’s is hands-down your best bet, and with five or six locations, you’ll probably be able to find one wherever you’re staying. But if it’s an absolutely genuine Pittsburgh moment you’re looking for, go to DeLuca’s in the Strip District. The experience of dining at DeLuca’s is not unlike being on the stage of a movie set in 1955.
That’s an incredibly difficult question, but only because Pittsburgh has so many wonderful dive bars. For my money, it’ll always be tough to beat Dee’s Café on the South Side, although Gooski’s in Polish Hill comes mighty close. There’s a great sense of camaraderie there, and local punk and garage-rock bands play live on the weekends. Heck, even David Byrne stopped by Gooski’s when he was in town!
Pittsburgh is undoubtedly a car-driving type of place, but unless you’re going way out to the suburbs, it’s a cinch to see the city by bus. For a cheap city tour, hop on a 54-C bus, which will take you through a number of Pittsburgh’s best neighborhoods: Oakland, Bloomfield, the Strip District, the North Side, the South Side, etc. (Ask the driver if he’s South Side or North Side bound.)
My personal favorite is Squirrel Hill, one of the largest Jewish communities in the eastern United States. The neighborhood is essentially a mini-city, complete with everything from cafes and bookshops to kosher grocery stores and bagel bakeries.
Unfortunately, Pittsburgh’s only youth hostel closed its doors a few years back, and budget accommodations are hard to come by. However, there’s a very affordable B&B on a residential street in Shadyside called The House of Zen. The proprietor only advertises on Craigslist, and almost no one knows about this place. It’s definitely the best-kept budget secret in the city. There’s even a sunken conversation pit in the living room–it’s used for walking Zen meditation sessions, which usually take place on the weekends.
For the conservative crowd, that would be the Omni William Penn Hotel, an elegant luxury hotel that is nearly 100 years old. For something with a bit more flair, try the Renaissance Hotel in the Cultural District. If you’re a baseball fan, ask the Renaissance clerks for a room with a view of PNC Park, where you can literally watch a Pirates game from the comfort of your queen-sized bed. (The city’s best B&B, by the way, is the gay-friendly Inn on the Mexican War Streets, located on the North Side.)
I’d say summer, because Pittsburgh plays host to so many different types of festivals and events during that time of the year. There’s the Three Rivers Regatta (jet-ski racing, water sports), the Three Rivers Arts Festival (craft stalls, free outdoor concerts), and the Fourth of July fireworks celebration at Point State Park, which is something of Pittsburgh tradition. Spring and fall are fine times to visit as well, but winters can often be dangerously cold, so check the forecast beforehand if you’re planning a holiday-season visit.
The Children’s Museum of Pittsburgh on the North Side is fantastic, and the Senator John Heinz History Center in the Strip District has quite a few permanent exhibits that kids seem to enjoy. There’s also the hands-on Carnegie Science Center on the North Side, complete with an OMNIMAX theater. But my top pick is the North Side’s National Aviary, well known as the nation’s premiere bird park.
I’ve always loved the Three Rivers Arts Festival. It takes place over three consecutive weeks during the summer (usually in June), and because so many different galleries and arts organizations participate, the Downtown area is packed with contemporary art, folk art, and bizarre installations and sculptures for most of the month. There are also free outdoor concerts daily, with A-list bands headlining during the final week. (Patti Smith and Sonic Youth both played recently.)
It was rated “America’s Most Livable City” by Rand McNally’s Places Rated Almanac, twice: once in 1985, and then again in 2007.
