Dining

Chili and Cinnamon Rolls Are a Surprisingly Fantastic Combination

This school lunchroom staple is hugely popular in many Midwest states
Chili and Cinnamon Rolls Food Pairing
Photo: Tasting Table

Peanut butter and jelly, burger and fries, grilled cheese and tomato soup—some foods simply go better together. But how about chili and cinnamon rolls?

This surprising combination has been a staple on school lunch menus for decades in states around the Midwest and West, and the seemingly preposterous pairing has incited many heated arguments with Southerners and East Coasters.

Karen Grubb, a cook at Conrad Public Schools in rural Montana for the last 15 years, used to head in around 5 a.m. on chili day to start the cinnamon rolls. "It took me a few days just to get ready for that day," she says.

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She'd make about 700 rolls—400 to feed the students and the rest to be bought up by teachers, parents and others in the community enticed by the smells of warm cinnamon wafting out through the windows. One of the hallmarks of Grubb's rolls was a thick layer of sweet, creamy frosting, which she whipped up with 50 pounds of confectioners' sugar, vanilla and lots of butter. 

"Chili and cinnamon rolls were a favorite among the students," Grubb says. "It was always the biggest day, for both students and adults."

Taking roll making very seriously was a tradition in Conrad. Before Grubb's time, Bonnie Breding was the baker for 19 years and worked in the lunchroom for three decades. She says it took five people to handle all the dough and form it into 35 rolls per pan. It was hard work, but "to see the appreciation on their faces and the 'yum' sounds made it all worthwhile," Breding recalls.

Due to new leadership, the rolls unfortunately aren't made fresh in Conrad's school lunchroom anymore. They're still served alongside a hearty bowl of chili, but both the soup and rolls come frozen. As for adults, they  don't have to travel far to find the pairing: A tiny little spot called Dusty's Bar & Grill in nearby Brady, Montana (population: 140), reportedly serves the combo for lunch on select days.

The origin of this combo is not clear, but the classic salty-and-sweet element certainly comes into play. A little cinnamon can add depth of flavor and a touch of earthiness to chili, so dipping a carefully torn-off piece of roll into the stew makes perfect sense. Plus, the thick frosting on the roll makes it basically dinner and dessert in one, so one could argue it's an affordable way to feed a family.

Montana isn't alone in its appreciation for the combo. The pairing is also found in school lunchrooms across Kansas, Nebraska, Iowa, South Dakota and Colorado, among others. And since nothing compares to homemade, restaurant chain Runza—based in Lincoln, Nebraska—has been serving chili with cinnamon rolls since 2007, when it purchased the recipe and rights to the famous rolls of the (now-defunct) Miller & Paine department store. The combo is a top seller, especially during cold weather, but still has its skeptics. 

"The debate is a divisive one, and we get many comments in support of both sides each time we post a chili/cinnamon roll message on social media," director of marketing for Runza Becky Perrett says.

Whether you grew up with this pairing or think it's crazy, the old adage holds true: Don't knock it 'til you try it. Just like Conrad second-grader Travis Hoy discovered the day he found a precious stone lost from one of the baker's rings in his cinnamon roll, you never know when you'll find a diamond in the dough.

Kelsey Ogletree is a freelance writer in Chicago covering food, fitness and travel. Follow her on Instagram at @gounearthed.

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