Jon Ross-Wiley

Age: 44

Height: 6'0

Weight: 192lbs

Date of Birth: 9/5/1973 

Born: New Haven, CT

Lives: Greenwich, CT

Course Specialty: 

Short to Long Distance

OCR Coach: Yancy Culp

OCR Team: Spartan 4-0

Jon Ross-Wiley OCR Obstacle Course Racing athlete results


Jon grew up in New Haven, Connecticut and has been a lifelong New Englander, attending Bowdoin College in Maine, living in Boston for 10 years, and currently living in Greenwich, CT with his wife and two children. Jon has dedicated his professional life to education; working in schools for over 22 years. Since 2012, he has been serving as an elementary school principal and relishes his time working with children. 

As an athlete, Jon has always been a competitor, playing football and lacrosse through college and continually seeking the next challenge. Thankfully, the world of OCR has opened the door to numerous challenges, which Jon has approached head-on with determination, grit, and a commitment to being the best possible version of himself. Jon continues to race regularly, taking-on long and short course formats and everything in-between.


  • Spartan Ultra World Championship Qualifier, 2018
  • OCR World Championship Qualifier 2016, 2017, 2018
  • OCR North American Championships Qualifier 2017, 2018
  • Spartan Double Trifecta 2017
  • Spartan Trifecta 2016


  • Savage Race Pro, Boston - 7th Place AG
  • Bonefrog Elite Challenge, New Jersey - 6th Place AG


  • Spartan Beast Competitive, Tri-State - 4th Place AG
  • Spartan CitiField Stadium Sprint Competitive - 5th Place AG
  • Spartan Sprint Competitive, Tri-State  - 11th Place AG


  • CitiField Stadium Sprint Open - 5th Place AG


What was your first obstacle race and why did you do it?

My first obstacle race was Rugged Maniac in Brooklyn, NY in 2014. I was looking for something new and different that would allow me to get out and compete!

What drives you to compete?

I have always had an inner drive to push myself as an athlete but, as I have gotten older, other factors have played in. I am driven by my children because I want to show them that hard work pays off. I am also driven by people I know who would give anything to compete but can’t due to physical limitations beyond their control. My fellow OCR athletes drive me as well. OCR is a great community.  

If you could run an obstacle race anywhere in the world, where would it be?

Japan is on my bucket list of places to visit…adding a race would amazing! 

What interesting fact do most fans of OCR not know about you?

I used to cater dinner parties featuring local foods.

Who is one of the OCR athletes you admire most and why?

Yancy Culp. Yancy has been such a force on the OCR scene as a competitor and a coach. As a Yancy Camp member, I have gotten to know Yancy a bit through his amazing commitment to personally connecting with clients. He is positive motivator, athletic (and life!) coach, and family man…not to mention a cancer survivor! Huge inspiration.

If you hadn't found OCR, in what sport(s) would you be competing?

Great question! I might have continued playing lacrosse in my local league. That said, I can no longer imagine NOT being involved in OCR.

What are your goals with OCR?

My goals are to continue to improve and stay healthy each season. I’ve moved from Open to Competitive (now Age Group), and have started to dip my toe into the Elite heats. An Age Group podium is my most immediate goal.