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Curiosity, community and childish nonsense: The Chicago race director redefining the ultra running experience

  • 8 hours ago
  • 3 min read

Ally Gregory, non-binary race director and founder of CUSS Running and Timely Nonsense ultra race in Chicago.

By Henry Howard

 

Creativity. Curious. Childish.

 

Those are some of the descriptions that came to mind as I reviewed my interview with Ally Gregory, the race director and leader of the Curious Ultrarunners Secret Society (CUSS). Their Chicago-area trail and ultra races focus on fun, community and inclusivity.

 

“As a non-binary race director, I understand the importance of being intentional in creating that space so all runners feel that they belong there,” they say. Gregory is optimistic that in 2027 they will be able to launch a new race with the same vibe, this time in Iowa.

 

For their contributions to inclusive trail and ultra races in Chicago, Gregory is my featured race director for July, the 31st in this series. In January 2024, I kicked off this monthly feature to pay tribute to the trail and ultra race directors who make the sport great.

 

To see previous RDs featured, they are all available here. If you have any nominations, feel free to email me here or fill out this form.


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Ally Gregory, race director of CUSS Running / Curious Ultrarunners Secret Society in Chicago


Ally Gregory Chicago-area trail and ultra races focus on fun, community and inclusivity.

Question: Why did you get into race directing?


Answer: To create this vision I had of a Chicago community of trail and ultra runners who truly lifted each other up and all valued diversity and inclusivity. As a non-binary race director, I understand the importance of being intentional in creating that space so all runners feel that they belong there.

 

Question: How did you get your start as an RD?


Answer: I volunteered at a lot of events in my first 10 years of trail and ultra running. Through that, I was lucky enough to befriend a couple of RDs who mentored me and answered all my questions when I first started directing. It was a wild time because my first race was one of the first events post-COVID to happen.

 

Question: What’s the most interesting thing you’ve learned about yourself since you became an RD?


Answer: I really solidified that I’m super introverted. I love the events and getting to meet everyone, but it does take me a few days to recharge.

 

Question: What’s your best piece of advice for someone who wants to be a race director?


Answer: Volunteer at events before race directing. It allows you to understand the logistics of event planning and see things you don’t get to see when you’re just running an event. Also, reach out to directors of races you love to chat with them!

 

Question: What’s your favorite race to direct?


Answer: I love my event Timely Nonsense. It’s your typical timed event on a .97 mile loop at a city park in the middle of Chicago. It’s so fun to get to learn all the runners over the course of the day and see how they interact with each other. Plus, at the top of every hour I issue a silly running challenge like do airplane arms or go down the slide at the playground.

 

Question: What’s your favorite race to run?


Answer: There’s a local race here called the Paleozoic 25K/50K. It’s been around for over 10 years and happens every fall and spring. It’s funny to keep going back to the same course and seeing the same runners year after year.

 

The Timely Nonsense timed ultramarathon is held on a loop course in Chicago, directed by Ally Gregory.

Question: Tell me about a funny experience as an race director and what you learned from it.


Answer: At my Childish Nonsense trail race, I have a magician on course just doing tricks and distracting the runners. It’s so fun. I was nervous the first year he was on course, because I didn’t know what the runners’ reactions would be. I just knew that I thought it was funny. When the runners came in laughing about it, I knew it was the right choice. This gave me confidence that even though some of my ideas are silly, there’s still room for them in the running space.

 

Question: If a runner can only do one of your races ever, it would be ....


Answer: Timely Nonsense trail race. You will leave the race with new, lifelong running friends, guaranteed.

 

Question: What exciting project do you have in the works?


Answer: I’ve had an idea for a couple of years about directing a trail race in Iowa, that I’m hoping to finally execute in 2027.

 

Question: Where can runners find out more about your inclusive trail races near Chicago?


Answer:

 


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