A slice of summery heaven graced Champaign-Urbana within the lively halls of Esquire Lounge on Saturday for the third annual Pineapplefest.
The event drew crowds seeking solace from the frigid weather to indulge in pineapple-centric food and drink, listen to yacht rock performed by Jake and Jackson Tartar and shop gifts from local businesses. Esquire also offered free “Pineapplefest 2025” souvenir cups to the first 200 people who ordered a pineapple margarita.
“We’ve done it in January every year because, after Christmas, there’s not a lot going on,” said Jackie Carlson, manager of Esquire. “We make a house-made pineapple-infused tequila, so we leaned into that theme and created food and drink specials.”
According to Carlson, Esquire has been making its pineapple-infused tequila for 20 years. Mike Cochran, who now owns Black Dog Smoke & Ale House, proposed the idea. Since then, the concoction has become a staple for the bar.
The event that began based around Esquire’s specialty drink — the pineapple-infused margarita — has become a popular gathering for many locals, leaving almost all seats taken by noon, according to Carlson.
The vibe in the lounge was distinct compared to the outside — pineapples hung from the ceiling, and lanterns and paintings littered the walls as snow lingered outside the building.
“It’s something to bring the community out,” said Justin McMullen, bartender at Esquire. “This is just an event to uplift your spirits during the wintertime, when it’s normally a little dull, a little cold, and it just reminds people of the summer.”
While the patron community is important to Esquire, it also uses this event to connect local businesses. A table in the second room of the restaurant had pineapple-themed ashtrays, jewelry, clothing and even real pineapple plants.
These goods were brought by local shops from the area: Plant Mode, Fire Doll Studio, Suzu’s Bakery and Jos. Kuhn & Co. This year was the latter’s first time vending at the Pineapplefest.
“We’re excited to participate in the event this year,” said Kyle Ohm, manager of Jos. Kuhn & Co. “I brought tropical-themed Tori Richard Hawaiian shirts, which were made in Honolulu.”
The festivity was filled with pineapple-themed drinks, crafts and food. Esquire’s head chef, Chrissy Tucker, had the creative freedom to curate a menu centering around pineapple.
The menu consisted of Cambodian pineapple soup, pineapple upside-down cake and Hawaiian pizza, along with other tasty delights. It also featured non-alcoholic pineapple cocktails to pair with these dishes so everyone could participate in the fun.
The inclusivity of the menu is reflected in the range of people who attend the Pineapplefest, as it becomes more of a staple every year.
“People look forward to this event each year, and it’s just grown as the turnout gets bigger and bigger every year,” McMullen said. “It’s a different crowd than everyday crowds. You get people coming here just for this event because they’re trying to lift their spirits up, too, especially in the dull drum of Illinois winters.”
As the yacht rock filtered through the building, lively chatter between tables over pineapple-themed cocktails gave the warm feeling needed during these cold winter months. Carlson said this socialization is one of her favorite parts of the event, as it’s encouraging to see regulars — who usually come on different days — come together for this event.
While this event has already exceeded what Esquire originally thought it would be, Carlson said they hope it continues to get bigger. During the rough winter season, The Pineapplefest provides some warmth, drawing locals out of their hibernation.
“Hopefully even more people can come out next year around the same time and just experience something different,” McMullen said.
gzmeans2@dailyillini.com
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