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Onwards and Upwards: Welcome Diana Hildebrand, Our Newest Coach

At the heart of the League’s Smart Cycling program lies a mission to train and empower League Cycling Instructors (LCIs) to teach bike education nationwide. But who trains the trainers? Behind the scenes, a crucial force drives this initiative forward: our dedicated coaches. 

Learn more about all of our League Cycling Coaches here. 

Becoming a coach isn’t easy; it takes tenacity, years of teaching, and the recommendations of experienced coaches, and League staff. 

Today, we proudly announce the addition of a new member of our small but mighty coaching team: Diana Hildebrand. Diana is a longtime LCI who wears many helmets: founder of DevahD Cycling, Shero for the Cleveland chapter of Black Girls Do Bike, and Education and Outreach Manager for Bike Cleveland.

On top of that, she was the League’s LCI Spotlight in July 2021 and recently won the League’s 2024 Educator of the Year award at the National Bike Summit in March – what a rockstar! 

When Diana’s fellow LCIs in Cleveland heard the news, they asked us to make sure people across the country knew how much they love her “dedication, enthusiasm, and sincerity in wanting to build a safe and inclusive bike culture for not only Northeast Ohio, but for the country.” They say her leadership, drive, and mission to get everyone to “have fun on two wheels” keeps the Cleveland LCI crew positive, active, and stoked to keep coaching.

To celebrate this milestone, we took a virtual trip to Cleveland to chat with Diana. Read on to learn more about our newest coach.

What does becoming a League Cycling Coach mean to you?

Becoming a League Cycling Coach means so much to me because for one, it was a part of my mid-term goal when I became a LCI 5 years ago. It shows that I have a true passion and love for teaching everything biking and being an inspiration to others, from becoming an LCI to wanting to get back on their two wheels of fun and learn how to ride with confidence and skill.  It means that I will be able to usher in more LCIs who are just as passionate about cycling to lead the way and continue to educate and be a resource to their organization and/or community. 

How did you first get into biking?

I can honestly say that biking found me in my late 30’s and I haven’t looked back since.  Of course, I learned how to ride a bicycle as a child but that was short-lived once I became involved in other sports — something we educators have often experienced with youth. But, what brought me back to cycling started with physical therapy. After sustaining a bad break while playing women’s tackle football, my PT had me on a spin machine to maintain flexibility with my ankle. After moving from Pennsylvania, I was still looking for activities to keep me moving. I didn’t necessarily want to get back into football — even though I loved playing, I needed a better alternative after sustaining some serious injuries. During my 36th birthday, I looked on Craigslist and found a $50 men’s Schwinn Road Bike — now called Ruby Rider. I biked my first 8 miles, which took me forever, but absolutely fell in love with biking!

How did you first become interested in teaching? 

It all started with me being left behind on a bike ride.  We are all faced with situations where we have a choice to either give up or keep going.  I chose to keep going, find out everything I needed to know and make a promise to myself that I would never leave anyone behind on a bike ride like I was left.  I also made a promise to be of support to those who wanted to learn how to bike.

What is a favorite memory of teaching cycling education?

I love questions like this because it brings back all the wonderful memories and moments I have shared with youth, adults, seniors, fellow LCIs, and coaches.

Thinking through this question, I can honestly say that my favorite memory as a cycling educator was teaching my first youth bike camp for middle schoolers — from watching one of my students learn how to ride a bicycle for the first time to seeing the group take pride in riding their first six miles together.

Diana (front row on the left) at a recent LCI seminar in Cleveland, Ohio.

Congratulations, Diana! We can’t help but be moved by this new Coach’s unwavering dedication to spreading the joy of Smart Cycling. With every testimony, we witness how our League Cycling Coaches and League Cycling Instructors are truly changing the world one bike lesson at a time! If you would like to join them, start by learning how to become a League Cycling Instructor — the first step to becoming a League Cycling Coach.