Out-of-towner happily finds herself in a pickle at festival

As I venture Downtown on Friday afternoon, the Boulevard of the Allies is packed with Pittsburghers wearing all-green attire and holding pickle-shaped balloons in honor of the weekend’s big event: Picklesburgh. I’m an out-of-towner this summer, but everyone I’ve asked has assured me that it’s a “pretty big dill” around here. 

The festival, a collaboration between Pittsburgh Downtown Partnership and Kraft Heinz, only dates back to 2015, but each year, it’s grown. This time, organizers were forced to relocate from the Rachel Carson Bridge, because it couldn’t hold all the vendors and crowds.

This much passion for pickles feels uniquely Pittsburgh to me. It’s both an ode to the Heinz company’s historical impact on the city and a celebration of the quirky tastes that yinzers hold dear. 

On the scale from pickle hater to pickle fanatic, I’ve always fallen somewhere in the middle. My early childhood memories include my father eating pickles, peanut butter and cheese with crackers and my baffled mother wondering how such a combination was edible. I took a stance of moderation then — and now, as the sun beats down on me, I’m determined to come in with an open mind. 

The goal? Sample a range of the many items that Picklesburgh has to offer and report back to those who might also be on the fence. I determined my evaluation criteria on the bus ride over. I’ll give scores out of 10 in three categories: “dill-iciousness” (flavor), whether I “relished” the experience and, finally, commitment to the pickle.

I decide to start off my journey with a drink — after all, it has just hit 4:30 p.m., the time when the festival can start serving alcoholic drinks other than pickle beer. I join the line for Dianoia’s Eatery, which builds quickly out of nowhere as soon as the clock hits happy hour. 

During the wait, I strike up a conversation with Jen Ball, her niece Danielle Stark, and a friend group that I will soon learn spans two generations — and includes a heartwarming Picklesburgh love story. 

But first, it’s time to sample our cocktails. I opt for a Pickled Limoncello Spritz, which contains a spray of pickle juice on top that the vendor assures me is “sorta subtle.” The members of the group I’ve just befriended order the same, as well as a Pickled Aperol Spritz.

Pickled Limoncello Spritz from Dianoia’s Eatery

Dill-iciousness: 8/10.

Relishing experience: 9/10.

Commitment to the pickle: 6/10.

Danielle and I agree that the spritz has all kinds of layers — the first sip is deceptively strong limoncello, the next dominated by dill. She jokes that the drink has awakened a “drunk scientist” within her: “Is the pickle brine more dense than the alcohol?” 

The sour tang of the limoncello does blend well with the brininess when you can get a sip featuring both flavors. The more we sip, the more it seems to taste like pickles. I’m all right with the slow build, but the consensus among the group is clear: It could be more pickled. I’m told the Aperol spritz achieves this goal, with a more potent pickle punch. 

While we sip our spritzes, I inquire for more details about the Picklesburgh romance. Back in 2018, Danielle hosted her friends Maddie Calder and Emma Weeber for the festival. Before, the two had just been friends. But somewhere amid the pickle magic, they began dating.

Danielle jokes that that very first festival established her as the captain of Picklesburgh, and one of a set of eternal third wheels that includes Alix Sward and Maddie’s sister, Alexa, who round out the Picklesburgh group. 

“We were not dating before Picklesburgh,” Emma says. “But everyone thought we were. I guess Picklesburgh, you know, inspired the confidence for me to ask you?” she says, turning to her fiancee, Maddie. “I think we just had a really fun weekend,” Maddie confirms. 

In the interim, Maddie and Emma adopted a pug together — and named it Pickles. By the time the next Picklesburgh rolls around, the couple will be married. 

Pickle Egg Roll from Le’s Oriental

Dilliciousness: 6/10.

Relishing experience: 6/10.

Commitment to the pickle: 7/10.

I leave the group with a newfound belief in the power of pickles and head to pick up one of the top recommendations as a snack: a pickle-filled egg roll from Le’s Oriental. This line is pretty straightforward, although for a moment, smoke from the grill blows directly into my face (giving me flashbacks to the peated whiskey of last week’s feature). 

I consider whether I should instead get the mac and cheese egg roll, which does sound fascinating. That wouldn’t be full pickle immersion though, and I can’t stray from my mission. 

On the first bite, I’m sold on the crispy exterior, not too greasy, but fried enough to give a nice crunch. The combination seems natural enough — the crispness of the pickle stands out among the savory flavors and softer cabbage. I regret to say that one gripe does bring my overall flavor and experience score down: The very middle is still a bit cold, an unexpected and unwelcome surprise. 

It’s a shame — if the eggroll were heated throughout, it would have been spectacular. As it is, it’s still pretty good, just not quite the elusive pickle greatness I’m searching for. 

Strawberry Dill Lemonade from Sienna Mercato

Dill-iciousness: 8/10.

Relishing experience: 7/10.

Commitment to the pickle: 3/10.

Sienna Mercato is a tantalizing choice for my next beverage, boasting almost no line at all and menu options such as pickled caprese skewers. The vendor has spiked and nonalcoholic drink options, and this time I go for a Strawberry Dill Lemonade without Tito’s vodka — unlike the woman next to me, who asks for a double.

Right off the bat, it’s very sour and quite acidic, although not to the point of hurting my teeth, just as lemonade should be. The strawberry flavor is potent but natural. Staring closely at the cup, I swear I can see tiny strawberry particles. It’s a delightful strawberry lemonade — but the dill is nowhere to be found. 

I sip more intently, swirling my straw around in an effort to mix it. A tiny hint of dill is there at last, but not enough to warrant its inclusion in the name. On any other weekend, it would be a top-notch beverage. Now, I can only advertise it as a great choice for the unwilling pickle-hating friend you dragged Downtown.

Spicy Pickle Pizza from Junction Pizza LLC

Dill-iciousness: 10/10.

Relishing experience: 6/10.

Commitment to the pickle: 8/10.

Ever since I passed the massive operation that is the pickle pizza tent during my first walk around the boulevard, I’ve coveted a salty spicy slice. The only thing holding me back has been a massive line that seems to swell each time I glance over. Fueled by the strawberry (dill-less) lemonade, I start the 20-minute or so line-waiting journey. 

To make the time go by faster, I chat with Kisa Snyder and Carla Martin. This is Kisa’s fifth Picklesburgh and Carla’s second.

While in line, the pair lament that they’ll just barely miss seeing the 5:30 pickle juice-drinking contest — an event Kisa says she loves spectating but would never want to compete in. 

They agree that along with the competition, the drinks that balance booze and brine keep them coming back to the festival — so I recommend the spritzes as a follow-up to the Brine and Shine’s (made with rum and pickle juice) that they’ve just finished. 

Soon enough, we all make it to the end of the line. I’m a spice lover, so I have to go for the spicy option. An employee tells me it has only moderate heat (a 4/10 on a scale) in the form of Frank’s RedHot mixed with other sauce components, such as garlic. 

As I wander away from the tent, a few whispers follow me: “That girl has the pickle pizza!” I feel like the belle of the briney ball, the envy of everyone who didn’t commit to waiting. One woman stops me to ask where I got the slice, and I tell her — but caution her that the line is long. “Is it worth it?” she asks. I take a bite. “Absolutely,” I say with confidence.

I stand by that statement. This is, without a doubt, the best thing I’ve sampled so far. The pizza is made on the premises, so it’s fresh, hot and holds its shape. The flavors dazzle my palate: first garlic, then a touch of spice, then the salty Parmesan. Above all, the pickle integration is flawless — it’s sprinkled with dill throughout, so even if your bite doesn’t include a juicy sour slice of pickle, it’ll still taste like pickle pizza. I’m fully won over.

Condemned Cucumber Crunch from Papa J’s

Dill-iciousness: 6/10.

Relishing experience: 8/10.

Commitment to the pickle: 10/10.

Having finally experienced the culinary dream I was waiting for, it’s time to get riskier. So far, I’ve stuck with safer, more savory options. Before I leave, I want to try something bold, something that might make my mother question the sanity of the chef.

I spot a sign for Papa J’s Gelato, and check its menu for the strangest, briniest option. It’s staring me in the face: the Condemned Cucumber Crunch. I don’t ask for a sample, because right now I have no room for self-doubt.

My first bite is overwhelming. The gelato itself hits me over the head with intense dill flavor, a sourness emerging from the sweet cream. It’s topped with crunchy pickle-flavored potato chips, which add saltiness and strength to the whole thing. I won’t lie: It’s not my favorite. But I finish the whole thing, and I have to respect this dessert for being unafraid to embrace the spirit of the holiday. More than anything else I tried today, it committed to the pickle. 

Pickelsburgh continues from noon to 10 p.m. Saturday and noon to 6 p.m. Sunday on the Boulevard of the Allies, Downtown, the closing of which will affect traffic and transit.