While Pittsburgh is one of the smaller cities on the east coast, there’s approximately one million things to do no matter what season you travel there in. Let me tell you about a few of my favorite things to do when I have a day (or two) to kill in Pittsburgh!
1. Hit South Side for a Chill Friday Night Out
The South Side is packed with casual bars that require minimum effort but offer maximum fun. Bar hopping down Carson Street — Pittsburgh’s miniaturized version of NOLA’s Bourbon Street — is the perfect way to spend a low-key night out. There’s even a place for Philly fans exploring this side of the state at Cupka’s Cafe II.
2. Get Breakfast at Peace, Love, and Little Donuts
Guys, Peace, Love, and Little Donuts is incredible. The donuts may be little but that only means that you can try more of their 50+ funkadelic donut flavors in one sitting. My personal faves were the maple bacon and the peanut butter & jelly. The original location can be found in the Strip District.
3. Do Some Shopping at the Strip District
The Strip District offers a one-of-a-kind shopping experience. This unique little crevice of the city is lined with converted warehouses that now house a variety of nifty places to spend your money including gourmet food shops, old-style grocery stores, Pittsburgh trinkets of all sizes, and more.
4. See a Concert at Heinz Field
Heinz Field is traditionally known as the home of the Pittsburgh Steelers. But a lot more goes on at this beautiful field than some professional football. This stadium is one of the coolest places to see a concert — trust me. Check out the concert schedule and plan your trip to Pittsburgh around one of the many concerts happening there this year.
5. Walk the Three Rivers Heritage Trail
If you’re traveling to Pittsburgh on a budget, one of the best things to do is take a stroll along the Three Rivers Heritage Trail. You’ll get a great view of the city and most of your steps for the day.
6. Get Rowdy at Tequila Cowboy
The North Shore of Pittsburgh is home to some big and crazy bars. If you’re looking for a night out that you won’t forget, then head to Tequila Cowboy, the biggest and craziest of them all. Tequila Cowboy has a neat layout where you can travel from huge room to huge room and find one that fits the particular type of wild you’re trying to be that night.
7. Take a Stroll Down Walnut Street
Walnut Street runs right through Pittsburgh’s mellow Shadyside neighborhood and is adorned with one adorable little shop after another. Browse boutiques for clothes, jewelry, artisanal baked goods, and much more.
8. Have a Few Margaritas at Steel Cactus
While you’re on Walnut Street, stop by Steel Cactus. I was here during the summer and sat up on the rooftop deck and it was dreamlike. We had tacos and jalapeño margaritas and all kinds of tequila shots. This is a great place to day drink in the sunshine. But be careful — they aren’t messing around with the jalapeño. They are spicy.
9. Visit Blue Slide Park
To be totally honest, I’ve never personally been to Blue Slide Park. But during a recent visit to Pittsburgh, a friend of mine said that’s his top must-see place to take people that visit him. Not to mention, it had a special place in Mac Miller’s heart, who has a special place in my heart. Read up on Blue Slide Park’s interesting history here.
10. Grab a Treat for the Road at Oakmont Bakery
There’s bakeries, and then there’s the Oakmont Bakery. This family-owned and -operated retail bakery is something out of a dream. Everything is made fresh daily from the best ingredients, but what you won’t find anywhere else is the personal touch that they put into everything and the absolutely humongous selection of treats that they offer.
11. Ride the Incline to the Top of Mount Washington
More times than not, when you ask someone what to do in Pittsburgh, they’re going to tell you to ride the incline to the top of Mount Washington. There’s two different ones to choose from — the Monongahela and the Duquesne. Both will get you to the top where you’ll get spectacular views of the city and where the rivers come together.
12. Watch a Pirates Game at PNC Park
Even if you’re aren’t a baseball fanatic, you’ll enjoy watching a Pirates game at PNC Park. The park itself is in the perfect location to get a great view of the skyline no matter where your seats are, and you can drink there. Perfect day as long as it doesn’t rain.
13. Eat at the Original Primanti Bros Restaurant
Primanti Bros has become so popular nowadays but nothing beats eating at the original one in the Strip District. Not only do they still have most of the original decor that was here when its doors first open in 1933, but they’re also open 24 hours a day so you can get your fix whenever.
14. Get Some Fresh Air at Frick Park
As Pittsburgh’s largest (and arguably most beautiful) regional park, Frick Park offers endless opportunities for days when the weather cooperates even in the slightest. Utilize its 644 acres of scenic land to ride a bike, take a walk, have a picnic, or just spend time in nature.
15. Do a Cider Tasting at Arsenal Cider House
Nestled into the sleepy neighborhood of Lawrenceville is an itty, bitty little cidery that is the freaking bomb. On the outside, Arsenal Cider House looks like any other three-story family home on the block. On the inside, you’ll find a meticulously designed cider tasting room and all kinds of delicious ciders to choose from. (I highly recommend the Snowbound Cinnamon.)
16. Visit the Cathedral of Learning at Pitt University
The Cathedral of Learning at Pitt University is one crazy big building. I certainly don’t have the nuts to go up in it — truthfully, I can’t imagine studying in it like many Pitt students do. But man is it easy to appreciate from the nice, safe ground.
17. Explore the Four Carnegie Museums
No matter what you’re into, there’s a Carnegie museum for it in Pittsburgh. Well, there is if you’re into science, art, natural history, or Andy Warhol. These museums houses lifetimes and lifetimes of knowledge that are ready to be soaked up.
18. Have Lunch at Condado
I’ll tell you what — I love tacos. I live for tacos. I sniff them out every and anywhere that I go. But never in my life have I been so blown away by tacos before than I was at Condado in Lawrenceville. I’ve never had more options to create my own taco in my life — some were a swing and a miss but some of them were life altering. Also, if you go here and don’t get queso, you’re wasting everyone’s time.
19. Take in the Phipps Conservatory and Botanical Gardens
Sometimes there’s nothing more soothing than spending a day literally walking among the flowers. You can do just that at the Phipps Conservatory and Botanical Gardens, where they have dozens of different rooms, gardens, and displays to take in.
20. Visit the Heinz History Center
Yeah, Heinz is known for their ketchup (which is shameless douse 80% of the food I eat with). But there’s so much more to the Heinz legacy that you can experience firsthand at the Senator John Heinz History Center. Who is he? How did we get here? Why ketchup? Idk, visit the history center!
21. Eat Dinner at the Burgatory
Food is my favorite, and the Burgatory hits a spot I never even knew I had. Kind of like Condado, the Burgatory gives you a (HUGE) list of ingredients to put together your own burger. Slap as many types of cheese on there as you want…. and all the sauces. Don’t forget a side or five.
22. Spend a Day at Kennywood
If theme parks are your thing, Kennywood is the place for you. Kennywood is packed with all kinds of rides for people of all ages including “modern thrills” as well as “classic rides”. Even if rides aren’t your thing, you can spend the day shopping and getting your steps in while the thrillseekers get their fill of rides.
23. Take a Ducky Boat Tour
The first ever thing that I did in Pittsburgh as a kid was take a Ducky Boat Tour. If you live under a rock, these boats are… well, boats with wheels. They tour the streets of Pittsburgh and then roll right out onto the river to finish off the tour. Fifteen years later, I will highly recommend it.
24. See a Penguins Match
Whether or not you actually like sports, hockey is great to watch. It’s fast-paced. It’s loud. Quite frankly, it’s violent and so sickly enjoyable to watch. And the Pittsburgh Penguins are a team of note. At one time, they were the best in the league. If you can score tickets, this is a great way to round out a weekend in Pittsburgh.
Enjoy your trip to Pittsburgh!