In a few weeks, when everyone is fleeing Pittsburgh for the summer, I’m staying right here for a Pittsburgh summer! There are so many local things I always want to do during the school year, but never have time for. So, my roommates and I are making the ultimate Oakland summer bucket list. If you’re also staying in Pittsburgh (or visiting during the warmer months), you should definitely try some of these too.
- Try A Restaurant From Every Neighborhood
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Pittsburgh has so many hidden gems, yet I somehow end up at the same spots over and over. I have my go-to favorites: Emerson’s in Market Square, Noodlehead in East Liberty, Kujira in Shadyside, and The Porch in Oakland. And don’t get me wrong, I’ll still be hitting those this summer. But, I’m challenging myself to try a new restaurant in every neighborhood to branch out and really take advantage of Pittsburgh’s diverse (and underrated) food scene.
- Pirates Game
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I might not be a huge sports person, but I love a sporting event; getting dressed up, heading downtown, walking across the yellow bridge to PNC Park, taking pics, and enjoying a game-day glizzy. That is something I can get behind! The Pirates still have plenty of games (150+) left this season, so you have no excuse not to go to at least one.
- Picklesburgh
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Over the past year, I’ve been forcing myself to like pickles purely so I can fully enjoy Picklesburgh. Priorities. Pittsburgh’s iconic pickle festival is July 16–19, 2026, in Downtown. Across the Sister Bridges, you’ll find pickle-flavored food and cocktails, live entertainment, and even a pickle juice contest. I’m determined to finally be a pickle person by then.
- Jam On Walnut
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I’ve wanted to go to Jam on Walnut since freshman year, and now that I’m 21, it’s even more appealing. There’s live music from local bands, shopping at local boutiques, and great food and drinks. Plus, Shadyside is already one of my favorite neighborhoods, so this just feels like the perfect summer night.
- Bottomless Brunch
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Like I said, Pittsburgh’s food scene has so much to offer, and somehow I’ve never been to bottomless brunch! I’ve heard amazing things about The Yard, The Urban Tap, Ritual House, and The Abbey, so this is definitely happening this summer.
- Pittsburgh’s Arts Scene
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This city has so many festivals, venues, and performances that I didn’t even know existed. Between Stage AE concerts, the Three Rivers Arts Festival, the Millvale Music Festival, Phipps, the Mattress Factory, and the Carnegie Museums, there’s always something going on. I’m making it a goal to take advantage of the opportunities this summer.
- Night Out On The Town
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And finally, if you’re 21, Pittsburgh’s going-out scene has endless options. There are so many places on my list to try. For a more chill vibe and a good cocktail: Space Bar, the Spritzery, the Summit, Bakersfield, Barcelona Wine Bar, Tetto at Sienna Mercado, and Hidden Harbor. If you want a bigger night out: North Shore (Tequila Cowboy, Jason Aldean’s, McFadden’s), Bootleggers in Oakland, or Howl at the Moon downtown.
I hope this inspires you to fully take advantage of your Pittsburgh summer!