In the ’80s, the hot dog stand made a few small menu changes: It added cheese, ketchup and relish as topping options. Then, a few years ago, the restaurant added a Chicago-style dog for some variety. But there are no French fries or fancy, bacon-wrapped anything — even 75 years later.
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Cupid’s continued success is credited to Kelly and Morgan Walsh, the granddaughters of its original founder. In 2009, the sisters became third-generation business owners after their father suddenly passed away.
“There was no prepping for us to take it over, it was all sudden,” Kelly explained to In The Know. “I was doing my own job and it was just kind of like, ‘You guys have the opportunity either to just shut Cupid’s down or figure it out, and take the reins, and keep going.'”
Kelly and Morgan had both worked at Cupid’s in high school, and Morgan credits that experience with helping them fully understand how much the store meant to its customers.
“We [would] hear all these stories from people coming in and they’d be like, ‘Oh my dad used to bring me here after little league practice in the ’70s’ … or people who come in and they would say that their mom was in the hospital on her deathbed, and the last thing she wanted to eat was a Cupid hot dog,” Morgan said. “When you hear that, when you hear those stories, we were like, ‘OK, we have to keep this going.'”
While Cupid’s has remained a staple in the community, the sisters have brought in their own twist: roller skating.
Last summer, Cupid’s started allowing customers to order from their cars, in order to abide by pandemic safety regulations. After the sisters repaved the parking lot, they just decided it would be more fun to skate to customers — rather than setting up a conventional drive-thru.
“There was one day where I was like, ‘I wonder if I could skate at the store while I’m making hot dogs,'” Morgan said. “It was so much fun and the customers loved it.”
Morgan noticed that, like Cupid’s itself, the skating brought back a lot of memories for the customers.
“This really is something that hits a chord with people,” she said.
“I think the roller skating and just talking to the customers and hearing how much it means to them that they’re grateful that we’re still keeping it going and just how happy it makes them that they still get to have that piece of their childhood back,” Kelly said.
“It is easy to get kind of bogged down in the day-to-day of running a restaurant,” Morgan added. “It’s a lot of hard work, it can be very stressful. And so when you read things like that, you’re like, ‘OK, we do more than sell dogs.'”
The sisters recognize how rare it is for the family business to still be bustling and expanding. They ship Cupid’s hot dogs nationwide now and have even launched an online ordering app. But even with these advancements, the foundation of the company stays true.
“One of the reasons that our grandparents started [Cupid’s] is that they said no matter what happened to the economy, people would always buy hot dogs,” Morgan said. “Here we are 75 years later.”
Cupid’s Hot Dogs does carhop services every Thursday from 4:00 p.m. to 8:00 p.m. at their Winnetka location.
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