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We’re not dreaming much about horses after our trip to Louisville, but we are thinking about how early we can leave Chicago on a road trip to Florida this August and make a must stop at Hi-Five doughnuts along the way. Owners Annie Harlow and Leslie Wilson share a passion for making amazing doughnuts (think Bourbon-infused goodness) with unique combinations to make you come back over and over again. (Trust us, we’re making plans). The team started out small with a food truck back in 2013—and have since grown into a brick-and-mortar location that you can’t miss when driving by E. Main St.

Lucky enough, the day we came by we ran into Leslie and we couldn’t resist asking a few questions!

What are the best places to relax in Louisville?
Iroquois Park, it’s absolutely gorgeous there. I love hiking/running this park. It’s never super busy and I always feel safe! It’s a hidden gem.

In Louisville, name three places you usually hang out with friends?
My friends and I love to eat, so you’ll most likely find us at Kashmir for their Indian Buffet or Vietnam Kitchen for lunch. As for drinks, you can find us at the Flea Off Market sipping a Flea Tea and shopping for vintage finds.

Any crazy doughnut idea that you might think you want to create?
We definitely want to do more savory doughnuts. Possibly a unique take on a hot brown soon! Yuuuuuuuum!

Where do you find doughnut inspiration?
Everywhere. I’m always on the look for new ideas. I love going to different ethnic grocery stores. I get a lot of ideas from that.

What are your favorite weekend trips from Louisville?
Annie and I love Chicago, so we go up there a lot. I also have a family lake house in Michigan that I frequent on the regular.

What is the most requested doughnut to date?
The Bourbon-Caramel Glazed with Applewood Smoked Bacon, FO SHO!

Do you keep a count of how many doughnuts you have made to date?
No, but it’s in the gazillions!

Lastly, you might start seeing more Hi-five doughnut around as they might start franchising soon!

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Henrique Kerch

I’m a Caracas native, living in Chicago. I have a passion for travel, culture, food, adventure and discovering new places off the beaten path. I still remember the first trip I took internationally as a child and the excitement that it was to know that everyone will speak another language. Traveling was cool—waking up early to make the trip to the airport, packing too much and then realizing it’s much better to pack light.

Now a travel writer, I get to see new places continually, check out new restaurants, and talk about my experiences. Just as I’m about to be done with a trip, I see myself at the airport daydreaming while staring at the departure board thinking about my next destination.