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Curious City’s Doughnut Crawl: Let’s divide and conquer!

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Note: This story was the first in a two-part answer to a question posed to Curious City. Alas, our doughnut crawl is long over, but below we list terrific doughnut shops, and we present chef Enoch Simpson’s taste guide. For more, including crawl results and a fascinating history of privately-owned shops in Chicago, click here!) 

Once in awhile we get a question submitted anonymously. Sometimes it’s challenging to answer those questions without following up with who asked it, but this particular question was straightforward enough:

Are there any privately-owned doughnut shops in Chicago? Which is the best?

A quick Google search takes care of the first part. Turns out, there’s a good number of privately-owned doughnut shops in and out of the city, and that number may be rising. Dan Weissmann is delving into the history of privately-owned doughnut shops, but for now, let’s jump to the second part of the question: Which is the best?

This is where you come in. While Curious City producers and editors are up for most challenges, we’re still just a team of humans and — the last time we checked — each of us has only one set of arteries. Our strategy? Divide and conquer! Many of you heeded our call to submit your favorite privately-owned doughnut shops. We’ve turned your list into a map of suggested doughnut shops and bakeries, and we threw in some routes to link them, to boot. Now, it’s time to put your money where your mouth is by joining the first-ever Curious City Doughnut Crawl.

The challenge

To find Chicagoland’s best privately-owned doughnut shop.

How to help


Pick a route from this map we created from your suggestions. Also, feel free to pinpoint any privately-owned doughnut shops we may have missed and add them to this map. It’s a public, editable google map, so anyone can edit it. (Remember: with great power comes great responsibility).


Open, download or print this handy-dandy guideto what makes the ideal doughnut (thanks to Chicago doughnut hero Enoch Simpson of Enoch’s Doughnuts and Endgrain for reference!)


Visit as many of the doughnuts stops on your chosen route as you can. You don’t have to visit every single one, but we’d like to think your decisions will be increasingly well-informed the more doughnuts you sample. If you go with a group of people, consider getting a variety of doughnut types and splitting them.


After you’ve sampled the doughnuts, rate each doughnut shop as a whole using the survey form we created right here.

You can certainly take notes at the shop and later submit the form on a desktop computer; however, it may be best to leave this form open on a smartphone during your doughnut journey and submit one survey during or directly after each stop.


Share your doughnut crawl with us!

Between now and our upcoming story, please send us photos of the doughnuts you tried on your route, the people you meet in the shop, storefronts, anything, really! Tweet us @WBEZCuriousCity, message us on Facebook, or email us directly:

We’ll be sure to post your thoughts and photos along the way.

So stay tuned. Stay in the loop. But above all, stay in touch with your sweet tooth.

The Dan Factor

What’s next? Well, recall that our doughnut-related question has two parts. Dan Weissmann (who you may remember from our adventures at The Morton Salt factory and Chicago and North Western Historical Society) is tackling the “serious” (aka, history-related) part, but it turns out he’s a fan of sugared dough, too, so there’s a good chance you’ll see him on his own doughnut route. On the map, we’ve conveniently labeled it “Dan's Route.” Dan will judge doughnuts with the same guide and survey that you do, and he’d love to see you during his trip. He’s already committed to hitting the doughnut highway on Friday, August 9, but watch our Facebook page or Twitter feed for more details.

He’ll have his follow-up story ready soon after.

Green=Day Trip Route  Red=North City Route  Blue=South City Route  Yellow=Dan's Route

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