At just about four hours from D.C. (as long as Beltway traffic doesn’t have other plans), Pittsburgh can be an ideal long weekend trip. This hilly and bridge-tastic city has a lot of character, as well as a burgeoning (if somewhat transient) food scene, and many cultural highlights.
For those mostly in it for the food, here’s how to spend a weekend’s worth of meals in the city (with some activity suggestions along the way). This guide is designed with flexibility in mind, with ideas for several arrival times on Friday and departures on Sunday. Heading in Thursday to get even more Pittsburgh action? Consider the alternate Sunday night path for your evening agenda.
Friday
Arriving around 1 p.m.? Ride the Incline, then grab some ice cream.
If you’ve got some afternoon time to spare, make your first stop one of Pittsburgh’s most iconic sites: the Incline. The city has two funiculars that have been around since the 1870s, and riding these historic cable cars offer unparalleled views of the city at the top of Mt. Washington. Take the Monongahela one up and back for a round-trip fee of $3.50; if you want to linger for a bit, there are a handful of bars within walking distance to grab a quick drink (Shilo Gastro makes a decent cocktail), or you can get some solid ice cream at DiFiore’s. For the true ice cream connoisseurs, one of your best options is about a 15-minute drive away at the institution Page’s on East Carson.
Arriving around 3 p.m.? Shop and wander around Lawrenceville.
The bulk of your evening and drinking will take place in this ever-changing Pittsburgh Neighborhood. Its main drag of Butler Street has some cute bars and shops to keep you occupied. Make sure to duck into Wildcard, a quirky card and gift shop. Feel free to pop into any bar that looks appealing (also nearby, the Church Brew Works, a Catholic church-turned-brewery with a menu of burgers, pierogies, and other Pittsburgh-centric dishes), but if you’re looking for more of a roadmap…
4 p.m. Happy hour at Grapperia
You don’t find too many bars dedicated to grappa, but this offshoot located behind (and affiliated with) neighborhood Italian favorite Piccolo Forno is all about the Italian spirit (amari are also a big focus). You’ll find several cocktails featuring the ingredients, but a flight is a great way to sample a few offerings. Bonus: It opens before 5 p.m. and is usually pretty empty beyond a handful of regulars at this time.
Another idea: Bar Botanico opens at 5 p.m. Fridays.
5:30 p.m. Meat plate at Morcilla
Justin Severino’s Spanish-leaning Morcilla is one of the best places in the city to sample charcuterie. Sidle up to the bar and treat yourself to the $30 plate (Severino is excited enough about the craft to spin off his own cured meat company, Salty Pork Bits), and maybe pair it with a little sherry.
Other ideas: Sibling to Umami down the street, there’s the Parlor Dim Sum from Roger Li, an updated take on Cantonese American dining, for snacks. It’s closed temporarily, but a martini with the impossibly skinny frites from French favorite Poulet Bleu is normally a move here. Ask for all the steak sauces for dipping on the side; you understand it’s extra.
7 p.m. Dinner at Pusadee’s Garden
This longtime haunt for Thai food got some new digs a couple of years ago, and the expansive, floral patio feels like something you’d be more likely to find in Southern California. Even if the weather won’t cooperate for eating outside, this place has more than atmosphere to recommend it — order dishes like tom yum spiked with shrimp dumplings, spicy Northern-style sausage, a thrilling mushroom larb, or an assertive pumpkin curry; vegetarians can eat very well here.
Other ideas: DiAnoia’s (book a reservation far ahead) or Piccolo Forno for Italian (reservations via phone only), Umami for omakase sushi (make a reservation), or the family-friendly Driftwood Oven for good sourdough pies.
9 p.m. Jazz at Con Alma
Wind down your evening at this cozy Ellsworth spot (there’s also a downtown location) for live music (and, interestingly, vegan food); keep an eye on the calendar to see who’s playing.
Saturday
8:30 a.m. Breakfast at Kelly O’s
This friendly diner caught the attention of Guy Fieri several years ago for its version of haluski, a cabbage and noodle dish with strong roots in Pittsburgh (his visit upped the diner’s business enough to allow them to expand to multiple locations). Be sure to make the dish part of your order, but there are plenty of other diner classics on the menu here, and some tasty specials like breakfast potatoes topped with breakfast gravy.
Other ideas: Depending on where you’re staying, Mediterra Cafe or a coffee and pastry from La Prima could be options. There’s also KLVN in up-and-coming Larimer, with breakfast tacos and burritos from Baby Loves Tacos.
10 a.m. Wander the Strip District
This commercial, industrial area of Pittsburgh comes to life on Saturdays with produce vendors, seafood wholesalers (take a quick wander through the epic Wholey’s and rub the pig statue for luck), Italian and Polish markets and delis (S&D is another haluski purveyor know for its pierogi), and a zillion vendors selling Pittsburgh team-related merch. Pennsylvania Libations is a fun stop with booze all from the state’s distilleries (they offer free samples, too). Once 11 a.m. rolls around, be sure to swing into Wigle, Pitt’s best distillery, for a flight or a cocktail (the saffron Negroni is a great pick). D.C.’s own Aslin now has a brewery outpost in this neighborhood, too, and they open as early as 6:30 a.m. for the breakfast crowd.
Noon. Visit the National Aviary
One of Pittsburgh’s treasures, find a dizzying collection of birds here, from the tropical to the arctic — owls, birds of prey, flamingos, and colorful showcase birds like the cock-of-the-rockwok. Be sure to keep your eyes peeled for Wookie, the Aviary’s beloved sloth — it’s no surprise that he’s often curled up and asleep high up in the trees, but when he’s active, he’s a sight to behold.
1:30 p.m. Lunch at Max’s Allegheny Tavern
You may have noticed from your time in the Strip District delis that Pittsburgh has a significant Eastern European population, and this classic has been around since the ’70s. Order any of the ’wursts here, plus spaetzle, schnitzel (five varieties!), potato pancakes, and more.
Another idea: Federal Galley food hall (Detroit-style pizza, Hawaiian fare, and more). Alternatively, if you have the wherewithal to plan ahead, consider booking tours of the Troy Hill Art Houses, three amazing head-to-toe installations inside what looks like an everyday residence from the outside. Nearby is Scratch Food & Beverage for really good neighborhood fare or Threadbare Ciderhouse for a vast array of ciders that will make you a convert, from the folks behind Wigle. This means, though, you may not have time for…
2:45 p.m. Trip to the Andy Warhol Museum
Find an impressive selection of works and exhibits from the pop art master here; he was born in Pittsburgh.
4:30 p.m. Happy Hour at Eleven
One of the best happy hours in Pittsburgh runs from 4 to 6 p.m. on weekdays at this restaurant from the Big Burrito empire. Wines, bites, and cocktails are all $9 and the snacks range from mussels spiked with kielbasa to fried curds in a beef bourguignon sauce.
Another idea: A drink at Southside cocktail bar Acacia, which opens at 5 p.m.
6:30 p.m. Dinner at Chengdu Gourmet
In Squirrel Hill, a neighborhood brimming with excellent Chinese options (not to mention Korean fare, Jewish food, and even a Laotian restaurant, among other choices), this Sichuan restaurant from chef Wei Zhu is a particular standout (it’s been on the semifinalist list for the James Beard awards many times). You’ll do very well with Sichuan dishes like double-cooked pork, dry-fried green beans, and anything cooked in a flaming pan; find a variety of offal dishes here, too.
Other ideas: African Eats, Kiin Lao (where D.C.’s own chef Seng Luangrath consulted on the opening), and Jian’s Kitchen, all in Squirrel Hill.
7:45 p.m. Drinks at Hidden Harbor
Tiki bars often face warranted criticism of cultural appropriation. But it’s worth noting for fans of the genre that Hidden Harbor isn’t just the best tiki bar in Pittsburgh — it’s one of the best in the country. Keen attention to detail shows on the hideaway’s cocktail list (with both original and historical drinks), elaborate decor (including commissioned pop art), and festive glassware; shark fins indicate the potency of various cocktails, and the snacks are great, too. There’s always a frozen cocktail option or two, and many more fishbowl-sized, dramatic drinks are meant for sharing (though no judgment if you decide to down an entire one yourself).
9:30 p.m. A late night soup dumpling snack at Taiwanese Bistro Cafe 33 — or a slice of pizza.
You don’t want a hangover after those sugary tiki drinks, so here’s one more chance to sop up some booze. Beyond having a strong Taiwanese menu, Cafe 33 makes the second-best soup dumplings in town, and they’re open until 10 p.m. on weekends (the xiao long bao at Everyday Noodles are probably a smidge better, but they close at 9 p.m.). If you’re ready to move beyond Chinese fare after eating so much of it at Chengdu (or you just lingered a little longer at Hidden Harbor, and Cafe 33’s already closed), instead try to decide which of Pittsburgh’s popular pizza joints serves your favorite slice — Napoli’s (open till midnight), Mineo’s (open till 2 a.m.), or Aiello’s.
Sunday
11 a.m. Brunch at Casbah
Another restaurant from the Big Burrito empire, this Mediterranean-focused restaurant is a nice option for brunch, especially because of its pretty patio surrounded by well-attended greenery. There are more breakfast-leaning options like sticky buns and a crab and roasted red pepper omelet, but pastas are a highlight at the restaurant, so why not have one first thing in the morning?
Another idea: Pamela’s for Pittsburgh’s favorite hotcakes, but note that they do not take reservations and often have a long wait.
1 p.m. Tour Phipps Conservatory
Pittsburgh has a gorgeous botanical gardens display worth a tour, and they often go all out with special exhibits (a recent one was inspired by the fashion of Pitt native Billy Porter). If brunch was enough to get you through dinner, consider also making a stop at the nearby Carnegie museums of Art and Natural History.
3 p.m. Sushi snack at Mola
Pittsburgh’s East Liberty neighborhood is worth a brief cameo for a snack and a wander. Surprisingly, one of Pittsburgh’s best tacos can be found at Duo’s Taqueria, a side project from, of all things, language learning app Duolingo, which is Pittsburgh-based. Sadly, it’s closed Sundays. Instead, head to Mola for some yellowtail jalapeno and Mola-style vegetables (good light options since brunch wasn’t that long ago).
Other ideas: Oysters at Muddy Waters Oyster Bar, okonomiyaki at Teppanyaki Kyoto, or arepas at the Colombian Spot.
Sticking around for the evening? Choose your own adventure.
Door #1: Head to Bloomfield
5 p.m. Quick beer at Trace Brewing
Local brewery Trace has a great inclusive vibe and plenty of space for a quick beverage before dinner; there are a few cocktails on draft for non-beer drinkers, too. Sadly, cocktail fans will not be able to make a visit to the excellent nearby neighborhood bar Tina’s, which is closed Sundays, but worth a visit if you are back in the area.
6:30 p.m. Burger at Tessaro’s
Neighborhood standby Tessaro’s has a pretty extensive menu and old-school feel, but people in the know (i.e. most people in Pittsburgh) go there for the burgers, which are excellent (the Cajun and the bacon bleu are two notable options, but there are several choices). The home fries also have a following, but be sure to order them well-done.
Another idea: Apteka, a short-listed James Beard nominee with vegan Polish fare and unusual specials like grilled sunflower heads, along with a compelling natural wine selection.
8:15 p.m. Karaoke at Cobra
End your time in Pittsburgh singing your heart out at the newish Cobra, which has private room karaoke (and a pretty extensive Korean/Japanese menu with tableside barbecue if you are still peckish). The lounge vibes here can often attract people dressed to party. Find Pennsylvania sake, Japanese whiskey, and more on the drink menu. Reservations recommended.
Or
Door #2: Explore Downtown Pittsburgh
5 p.m. Drink at the Warren
It can be hard to find a place that feels like a neighborhood bar downtown while still having some ambitious options — the Warren fits the bill with reasonably priced and interesting cocktails that often
