ten years ago, Pittsburgh didn’t have a pickle festival. today, it has one of the most recognizable and chaotic in the entire country.
the irony? Picklesburgh was never meant to be iconic. it started with a name tossed out in a conference room, a pitch for a 35-foot inflatable pickle, and a hope that maybe, just maybe, people would show up. what happened next? a merch frenzy, TikTok virality, with over 250,000 attendees.
I sat down with Jeremy Waldrup, President & CEO of the Pittsburgh Downtown Partnership, to talk about the festival’s very Pittsburgh origins, surprising growth, and what’s still to come. we talked while sitting on the Roberto Clemente Bridge, of course…
Sarah: how did Picklesburgh 🥒 actually start? take me back to the very beginning.
Jeremy: it all started around a conference room table. we were brainstorming ways to draw people Downtown during slow summer weekends when the Pirates were out of town and the Convention Center was quiet. we were inspired by the success of Pierogi Fest, and a former colleague, Russell Howard, tossed out the idea of pickles. another colleague, Leigh Frank, came back with the name Picklesburgh, and we were off. before I knew it, I was pitching the idea of a 35-foot inflatable pickle. the rest, as they say, is history.
Sarah: how did growing up in Pittsburgh 🖤 and your time spent here influence the way you approach Picklesburgh each and every year?
Jeremy: I’ve called Pittsburgh home for 14 years, and the city’s personality is baked into everything we do at the PDP. when we first floated the idea of a pickle festival and tied it to the iconic Heinz pickle pin, I knew we were onto something. that little green pin brought back memories for generations of Pittsburghers of factory tours, school field trips, and a sense of local pride. add in the fact that people have very strong feelings about pickles – love them or hate them – and we tapped into something uniquely Pittsburgh: nostalgic, quirky, and completely one-of-a-kind.
Sarah: what was the moment where you realized, “this isn’t just a festival anymore”? 👀
Jeremy: the first year really surprised us. we expected a good crowd, but what we saw was something more — people showed up early, vendors sold out, and there was a real buzz in the air. it felt like Pittsburgh had been waiting for something like this.
but the moment it truly felt bigger than just a festival was post-COVID, when Picklesburgh started gaining traction on TikTok. videos of the giant pickle, the crowds, and the food started spreading fast, and we saw people coming in from well outside the region. that’s when we knew it had grown into something with real staying power.
Sarah: how do you describe Picklesburgh to someone who’s never been? 🎤
Jeremy: it’s everything you never knew you wanted, and a few things you probably didn’t, related to pickles. no one asked for pickle lemonade or pickle cotton candy, but here we are. It’s part food festival, part street fair, and part cultural oddity in the best way. come hungry and ready to sample as many wild and wonderful pickle things as you can.
Sarah: what’s one decision you made early on that turned out to be way more important than you realized? 📝
Jeremy: the 35-foot inflatable pickle. at the time, it felt like a fun visual, but it quickly became the symbol of the event. people take photos with it, use it as a meeting spot, and it’s the first thing you see in every piece of coverage. it’s quirky, memorable, and somehow perfectly captures what Picklesburgh is all about.
Sarah: what was your biggest “we’ve got to figure this out now” or “this city 🌆 has my back” moment?
Jeremy: it was when we realized we had outgrown the bridge. the crowd was so large it spilled onto the adjacent streets, we knew immediately we had to start planning for something bigger. that next year, we expanded beyond the bridge. since then, Picklesburgh has become more nomadic, moving around downtown to fit the size and scope of a four-day festival that now draws more than 250,000 people. through every move, the city and county have been great partners to make it all possible. that kind of support is what’s allowed Picklesburgh to grow the way it has.
Sarah: what role has collaboration with our local community played in the festival’s success 🏆?
Jeremy: Picklesburgh wouldn’t exist without the creativity and drive of our local vendors. every year, they take what they know, and push it in new, pickle-inspired directions that no one knew they needed in their life. what’s even more impressive is that many of them come back year after year with new ideas, new products, and new ways to keep things fresh. their energy is a huge part of what makes this festival such a success. we couldn’t do it without them.
Sarah: what’s next for Picklesburgh and what’s the dream 💭? or, are we there?
Jeremy: every year, we want Picklesburgh to do more than draw a crowd. we want it to support our local economy, spotlight Downtown, and keep evolving. this year’s expanded footprint is a big step, stretching from PPG Plaza to the Sister Bridges and involving more Downtown restaurants than ever before. that kind of integration, where all of Downtown feels like part of the experience, is exactly where we’re headed.
Sarah: how did the giant flying pickle come to be? and, did it ever fall in the river 🦦?
Jeremy: the giant pickle was Russell Howard’s idea and I went home that night thinking he was completely out of his mind. but if you know Russell, you know he’s tenacious. by the end of the week, he had quotes from balloon designers across the country.
the original pickle never fell in the river (thankfully), but we’re now on version two. we did, however, manage to pop it in 2021 while trying to turn it into the world’s largest Christmas pickle ornament.
Sarah: what do you wish people knew about the work PDP does year-round 🕰 that Picklesburgh helps spotlight?
Jeremy: Picklesburgh is just one moment in a year-round effort to make Downtown vibrant, welcoming, and full of surprises. our team works every day to create experiences that bring joy to the people who live, work, and visit here. we want people to love Downtown as much as we do, not just during a festival, but on an ordinary Tuesday too.
events like Picklesburgh draw thousands into the neighborhood, and our hope is that while they’re here, they discover a new favorite restaurant, stop into a local shop, or make plans to come back for a show.
Sarah: what is one vendor creation that totally blew your mind? 🤯 I’m talking flavor risks or brand collabs that really stood out as “only-in-Pittsburgh” moments?
Jeremy: Turner’s Pickle Iced Tea and the IC Light Pickle Beer. they turned into instant hits because they tapped into something so uniquely Pittsburgh.
Sarah: 10 years in – what are people still totally getting wrong about Picklesburgh? 📣
Jeremy: that it’s just a quirky pickle festival. yes, it’s fun, but behind the scenes it’s a serious economic driver. it brings hundreds of thousands of people Downtown, supports local businesses, and shines a national (and even international) spotlight on Pittsburgh. Picklesburgh is one of the ways we tell a bigger story: that Downtown Pittsburgh is an incredible place to live, work and visit.
Sarah: what’s the wildest stat 📊 that’s surprised even you over the years?
Jeremy: just how much Pickle juice has been consumed – 800 quarts over 10 years.
800 quarts of pickle juice.
a merch table that sold out night one.
one flying inflatable that’s somehow still intact (well, v2).
from steel is about building what didn’t exist before: gritty, joyful, unexpected. that’s Picklesburgh in a nutshell. a festival that started as a longshot pitch around a table and turned into a national sensation.
this city shows up for weird, for fun, for flavor…and this one’s got all three.
