Looking for a weekend adventure during your holiday travel? Well, we’ve got the perfect pittstop for you — that’s right, we’re talking about the City of Bridges, the Steel City herself, Pittsburgh, Pennsylvania. With contemporary museums, a booming food and cocktail scene, and a sports culture like no other, a weekend in Pittsburgh has something for everybody. So pack your scarf, rev up your appetite, and definitely come thirsty — we’re spending 48 hours in downtown Pittsburgh.
Day 1
Station Square
Start the day at Station Square, an indoor-outdoor entertainment space that covers 52 acres! The space is bustling with restaurants, shops, and a stunning view of downtown Pittsburgh. Grab a coffee and some snacks to tide you over until lunch. Not to miss: Carol’s Confections and Bradley’s Books for all of your sweet-tooth and literary needs.
Ride the Incline
From Station Square, hitch a ride on the Monongahela Incline, America’s oldest operating funicular. The incline opened in 1870 and has transported millions of passengers up to Mount Washington, where workers began living during Pittsburgh’s industrial boom. The car travels up the mount for almost 370 feet at six miles per hour, leaving its passengers with a stunning view of the city.
Explore Mount Washington
After taking in the flawless panoramic views at one of the many viewpoints, stroll around the mountaintop, taking in all the quaintness of red-brick houses and old-fashioned ice cream shops. Grab a cone at DiFiore’s Ice Cream or stock up on baked goods at Grandview Bakery. Hungry for some lunch? Shiloh Grill is the way to go. Be sure to have an afternoon cocktail and brown-butter popcorn at The Summit before your descent back down.
Andy Warhol Museum
Despite his quintessential NYC image, did you know that Andy Warhol was actually from Pittsburgh? Head back to the downtown area and check out his namesake museum for your afternoon pop-art fix. Bonus: Visit on a Friday if possible — the museum has extended hours, until 10 p.m.
Pre-Dinner Drinks
Head two blocks down from the Warhol Museum to SoHo bar for happy hour and trivia. The bar is loaded with TVs, so you’ll be sure to catch whichever local team is playing. With 25 beers available (12 on tap) as well as a martini of the day, you’re sure to find a drink that fits your fancy.
Dinner at The Capital Grille
Treat yourself to an unforgettable dinner at The Capital Grille. Located on Pittsburgh’s Fifth Avenue, this swanky steakhouse offers up classic cocktails and delicious eats in a refined, elegant setting. Swipe through the drink specials and wine list on customized iPads brought to each table, while nibbling on seedy, fluffy bread baskets. We recommend the bone-in rib-eye or classic filet mignon; parmesan truffle fries, au gratin potatoes, and roasted wild mushrooms are not to be missed sides.
Music at Tequila Cowboy
Head to the newly opened Tequila Cowboy before 10 p.m. to avoid the crazy lines that wrap around the block. This three-room bar is bursting with energy, beer, and live music. The main area hosts a stage for live music, while the ’80s room glows with classic hits. But our favorite is the little room, tucked away in the back and reserved for karaoke!
Day 2
South Side
Get an early start by grabbing a coffee at Beehive and taking a walk down the South Side Riverfront Trail. Sip your coffee alongside beautiful views of the city while working up an appetite for lunch.
Afternoon on East Carson Street
Head back to East Carson Street for lunch, shopping, and, of course, afternoon drinks. Pub Chip Shop offers British fare for our fish and chip lovers, while Winghart Burgers has something for everyone (hello, fries menu and mac & cheese menu!). Work off that lunch with some afternoon shopping at Figleaf Boutique and Dave’s Music Mine record shop. And if you’re craving some sweets, S & S Candy & Cigar Co. is a step back into a 1950s candy store, brimming with every possible candy you could think of — definitely not to be missed.
Afternoon Drinks
You can’t go to East Carson Street and not profit from the plethora of awesome bars, perfectly situated within walking distance of one another. Head to Dee’s Cafe for cheap draught beers, multiple pool tables, and jukebox music. Jack’s offers a more retro vibe, with video games, daily beer specials (Monday-Thursday), and $8.75 pitchers. Prefer a speakeasy-like atmosphere? Acacia is your jam (opens at 5 p.m. daily).
Mattress Factory
If you prefer to save the drinks for later, head to the Mattress Factory for your alternate afternoon activity. This contemporary art museum hosts installations by resident artist from all over the globe. The museum was founded in 1977 and offers constantly changing exhibitions. It’s appropriate for all ages, too.
Catch a Game
Pittsburgh lives for its sports, so it would be a sin to visit the Steel City and not check out a game. Depending on the season, head to PNC Park or Heinz Field for a once-in-a-lifetime baseball/football experience. The energy of a Pittsburgh sports event is like no other — the fans are dedicated. While we prefer to nosh on stadium snacks, if you’re looking for a, well, bigger sandwich, there’s obviously nowhere else to go besides the OG Primanti Brothers.
Rivers Casino
Spend the evening gambling at Rivers Casino, Pittsburgh’s premier entertainment center. With nearly 3,000 slots, 90 tables, live music, and five restaurants, the possibilities are endless. But if gambling is not your thing, head back to East Carson Street for the best nightlife in the city. That’s where you’ll find us, cocktail in (each) hand.
Where to Stay
For upscale accommodations, Renaissance Pittsburgh Hotel is perfectly situated downtown, offering river or city views, free WiFi, and private patios (with selected suites). For lodging like a local, look for Airbnb apartments on East Carson Street or up on Mount Washington.
