It's Challenge Time

Updated: Apr 30

Who doesn't love a good challenge?

Since we aren't in person the 5K will not have a winner for best time. Instead we decided to have four competitions, one competition will run from March to May and the other three competitions will be in May.

Where's Curious City Challenge

As if we didn’t get enough Where’s Waldo as a child. Stay locked to Curious City’s social media channels to take part in the “Where’s Curious City?” competition. The Curious City team will either take a picture, write a haiku or record a voice memo with clues to a neighborhood featured in a Curious City story. The first people to guess the correct neighborhood will receive a shout-out on our Facebook group.

Photo Challenge

This challenge is simple enough. During your run/walk, take a photo of yourself along with something that peaks your attention on the route. It could be an abandoned building with awesome street art on the side, it could be a beautiful row home that you've never seen before, or it could be a random hill that comes out of nowhere. Choose whatever makes you say "huh" during your run/walk, take a photo of it and write about it. At the end of the challenge Curious City will take a look and pick their favorite. The winner will receive a shoutout on our race blog, on the Facebook group and on Curious City's Twitter account.

Voice memo Challenge

We want to hear your voice! During your run/walk, we want to hear your observations. Towards the end of your walk/run record yourself talking about what you saw, heard and what piqued your curiosity. All voicemails should start with your name, what neighborhood you are from, the Curious City story you chose and what neighborhood you are running in. The voice memo should be no longer than 2 minutes. To submit your voice memo email us at At the end of the challenge Curious City will listen and pick their favorite. The winner will receive a shoutout on our race blog, on the Facebook group and might be featured in an upcoming Curious City podcast.


Just because it's a virtual race it doesn't mean you can’t get dressed up. Show your creativity by dressing up as a famous Chicago personality, deck out in your favorite Chicago sports gear or there’s always an inflatable T-Rex costume you can put on. Take a photo or video of yourself running/walking in the outfit and tell us a little story about your choice in gear. Curious City will pick their favorite and pick their top three. The winner will receive a shoutout on our race blog and on the Facebook group.

We hope that you can participate in one of our challenges!

Vote for the next Curious City Question

Curious City runs on questions so of course we want you to use this race as inspiration to give us your best questions. On your route did you pass by a building that caught your attention? Ask us a question about it. Did you notice anything super interesting? Again ask us a question about it. During the month of May submit your questions and in the last week the Curious City team will pick their top three, participants will then vote on the question they most want Curious City to answer.

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