1. Banjo Night
Local charm, chicken finger baskets, and, well, banjos abound at this regular hoedown at the Elk’s Lodge. Grab a metal folding chair and take in the wonder of some 30 banjo players accompanying the stunning vocal stylings of D.J. Devine, a 60-something songstress in a cat sweatshirt whose rendition of “All of Me” gives Billie Holiday a run for her money.
2. Carnegie Museums
The Carnegie Museum does the whole “important collections of old objects” routine right. Andrew Carnegie smartly combined the city’s natural history and art museum under one roof, which means you can admire a badass collection of dinosaur bones in one room, then walk down a corridor to check out an impressive array of pop art paintings.
3. Allegheny Cemetery
This hilly stretch of Pittsburgh offers charm galore, of both the natural and macabre sorts. Filled to the brim with lavish mausoleums, ancient-looking headstones, full families of deer, husky groundhogs, and, on a summer night, the neon haze of fireflies, Allegheny Cemetery is the destination of choice for runners, picnicking romantics, and local history buffs alike.
4. Drinks at Kelly’s
Most cities with any self respect also come with a standard $10 to $14 price tag for their cocktails. But a drinking hole called Kelly’s offers their potent potables at $6 to $7, unless it’s the daily special, which is available for $4. Stop by on Thursday, when you can score a Moscow Mule and savor its sweet, affordable flavors on the tiki-esque back patio.
No matter your age, style, or taste in music, you’re bound to find a local dance night that suits your just right. From Brillobox’s hipster-heavy world music night to the Lava Lounge’s wonderfully cheesy ‘80s dance party to the catchy dance pop spun all weekend long at Remedy, this town has all of your dancing needs thoroughly covered.
6. The Bridges
A city that’s founded at the intersection of three rivers is bound to have bridges, sure; that’s just sound logic. But Pittsburgh’s collection of these geographical necessities is an accurate representation of what’s so alluring about this place: though diverse in design, the city’s bridges all seem both irresistibly industrial and stately in aesthetic. These feats of steel aptly exemplify the locale’s flair for fusing practicality and artistry in all the right ways.
7. Fort Pitt View
I moved to Pittsburgh, Pennsylvania after just two brief visits. However, any panic clouding my mind as I head into the city was quickly cleared by the astonishing vista offered by the trip from the airport. After following the highway through a cramped tunnel, the night opened up around me, revealing the most beautiful view of clustered skyscrapers flanked by dusk-hued waters. I was happy to be home.
8. The Strip District
In this goods-heavy stretch of Pittsburgh the purveyors are just, if not more, flavorful than their produce and other wares. You can find fish, flowers, meats, and Steelers jerseys in the Strip with ease, all pedaled by loud, raucously funny Yinzers (Pittsburghese for true locals) who are dead-set on making your shopping experience a memorable one.
The first Friday of every month finds the neighborhood of Garfield alive with a variety of locals – young families, struggling artists, well-dressed professionals, and all-around scenesters. This gallery crawl along Penn Avenue is as great of a people-watching experience as it is exposure to new works by up-and-coming artists.
10. PNC Park
It really doesn’t matter if you give a damn about baseball or not – PNC park is one of the most enjoyable spots in the ‘Burgh. Home to the Pirates, this ballpark has a breathtaking views from both the infield and the West End-facing patio. No summer is complete without a visit, even if you only stay long enough to down two Yuenglings and hit the dusty trail one inning shy of “Take Me Out to the Ballgame.”
11. Kayaking the River
Rivers are to Pittsburgh what waxed mustaches are to Brooklyn and Google Glasses are to DC: iconic emblems of the city. The best way to get to know the rivers is to rent a kayak and explore their shoreline. But don’t be put off by how athletic this sounds; it’s actually a wonderfully lazy venture that allows you to take in the sights without breaking a sweat.
12. The Duquesne Incline
It may be hokey, but this is one tourist attraction worth visiting once you’re a resident. Adorably old-timey and cheap, to boot (tickets run $2.50) this funicular climbs Mount Washington, the sharp ridge that overlooks downtown Pittsburgh. It’s full of out-of-towners by day, but surprisingly serene and romantic at night.
13. The Patio at Pusadee’s Garden
If you ask me, the best way to enjoy sublime weather isn’t hiking, biking, or all that sort of active stuff, but by sitting outside while shoveling food into your mouth. Pusadee’s Garden is a terrific little Thai place whose tiny indoor space is dwarfed by its lush wonderland of a patio. It’s BYOB, so bring some champagne to toast over your Pad Thai.
14. Drive Ins
For most metro areas, the drive in has gone the way of the dinosaur. But Greater Pittsburgh is the home of Dependable Drive In, a four-screen outdoor theater full of families and teens tailgating before the blockbuster gets rolling. There’s something so quintessentially “summer” about cranking up your radio and watching Robert Downey Jr. grimace from the comfort of your own car.
Unlike so many amusement parks around this country, the thrills you find inside of Kennywood — home to some of the oldest running roller coasters in the US — are authentic. “Is this wooden track going to collapse at any moment?” “How can a 90-year-old ride really pass modern safety regulations?” These are the sorts of wonderful fears that crowd your brain while at Kennywood.
16. Wigle Whiskey
Named after the Pittsburgh distiller who was sentenced to hang for refusing to shut down his illegal whiskey business, this distillery invites the public to take a tour of both the history of East Coast distilling and their own brand-new facilities, all while plying them with free tastes and plentiful sarcastic commentary. Talk about a history lesson most anyone can get behind!
17. Polish Hill
Pittsburgh is truly a town of distinctive neighborhoods, but if you were to ask a born-and-raised ‘Burgher which one has the most unique character, chances are they’d land on Polish Hill. The twisting streets that make up this elevated area offer gorgeous vistas revealed in the gaps between row houses, great rock-’n'-roll bars, and one of the most beautiful churches in the country.
18. Phipps Conservatory
Conservatories are like the symphony and reading “War and Peace”: everyone pretends they like them, but it’s rarely true. But Phipps Conservatory really is just as magical in person as one would imagine an oasis of exotic flora should be. From astoundingly gorgeous to confoundingly alien and weird, the plant life found within makes a visit to this elegant glass palace worthwhile.
19. Allegheny Observatory
A city is only as good as the quirky date-night opportunities it offers, but between banjo night, all the cheap cocktail joints, and the Allegheny Observatory, Pittsburgh has you covered. Try proceeding your Friday night stargazing tour with an evening picnic on the scenic grounds. It’s one way to deliver on that out-of-this-world night that your online-dating profile promises.
20. Estate Sales
I like weird, old things. Luckily for me, and all other antique enthusiasts, Pittsburgh is a goldmine for kitsch-y knickknacks. A cursory perusal of Craigslist on Saturday morning often proves to be a treasure map leading to a bounty of prim pillbox hats, Henry Mancini records, milk-glass vases, and even the occasional mid-century coffee table, all available for a song.
21. Haute Dogs
Nope, this ain’t Chicago, but yes, hot dogs are having a moment in Pittsburgh. For the pious and peckish, Franktuary dispenses modern takes on the classic frank from the back of a cathedral. If you prefer the traditional hotdog house setting, opt for either retro-tastic Station Street or the terrifically low-rent D’s Six Pax & Dogz and enjoy your wiener in laid-back style.
With bigger cities come the tradeoff of having picked-over thrift stores. Such is not the case for Pittsburgh, as their used-clothing shops usually house a wealth of wearable treasures that you would otherwise be forced to eBay to find. For extra great scores, head to the small thrift shops in the outer boroughs, like Community Thrift Center in the West Hills, and you’re sure to find that perfect pair of high-waisted Levi’s.
23. The Cathedral of Learning
It’s not easy to miss this local landmark as it looks like it’s straight from the set of “Game of Thrones.” This striking stone tower on the Pitt campus is full of classrooms, many designed in the style of traditional learning facilities from all over the world. Check out the view from one of the top floors or sit in a throne-like chair in the vestibule and pretend to lord over the stressed-out students.
No, technically this famed home isn’t in Pittsburgh, but it was built as the vacation home for the Pittsburgh-based Kaufmann family. This Frank Lloyd Wright construction is one of the most awe-inspiring man-made sights you’ll ever take in. Prepare to be baffled at just how contemporary all of Wright’s design details still feel, some 70 years after its completion.
25. Bowling Alleys
Many of Pittsburgh’s most enjoyable activities are anchored in a wonderfully old-fashioned sense of good, clean fun. This is also true of the city’s unofficial pastime, bowling. If you like a dash of karaoke when you go rolling, Arsenal Bowl is your spot. But if you prefer your alley to look just how you left it on your class trip in fourth grade, then check out Forward Lanes.
26. The Monroeville Mall
Pittsburgh is THE zombie city; it’s where George Romero first sparked our now full-blown obsession with brain-eaters, and there is no better way to pay homage to the undead than by visiting the Monroeville Mall. This sprawling retail destination is where Romero’s “Dawn of the Dead” was filmed, and I personally believe that the best way to celebrate this classic critique of consumerism is with a trip to Yankee Candle.
27. Sunday Night Series at Regent Square Cinema
If you’re anything like me, Sundays are reserved for simple, comforting pleasures. This small theater upholds that tradition perfectly with their Sunday night showings of classic movies, usually organized around a month-long theme. The last of the weekend feels so much more enjoyable when spent in the company of Jimmy Stewart or Woody Allen.
28. Construction Junction
Any new homeowner owes it to themself to visit this oasis of accoutrements for your abode. Channel your inner DIY dilettante and push through their collection of reclaimed doors, casted-off cupboards, and retro lighting fixtures to give your manor the makeover it deserves at a price point you won’t wince over.
As already stated, I can’t get enough of antiques or eating. Well, Zenith is the amazing place that allows me to combine these two obsessions seamlessly. Tucked away into a corner of the South Side, this wonderful place is both a vintage store and a brunch buffet spot. As if it couldn’t get any better, the buffet also comes with unlimited bundt cakes, of all different flavors.
30. Fish Fry
It doesn’t matter if you’re Catholic, or even if you believe in a greater power – all are invited to the Friday-night fish fries that take place in churches all over Pittsburgh during Lent. The menu offerings vary from location to location, so your best bet is to choose one that has beer and pierogis. But no matter where you head, you’re bound to find yourself full of homemade food prepared with extra love.
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