With the final leg of the Ultimate Cowboy Challenge at the Norfolk County fair fast approaching we wanted to take the opportunity to apprise all our competitors and spectators of some exciting changes.


For the 2019 show season we will be competing in our new sand pens located in the centre field. One sand pen will be designated as the warm up area/holding pen. Please ensure you are ready and in the holding pen prior to your race commencing. 

Walk through for the Gamblers Choice division will start promptly at 9:00 a.m. with our esteemed judge Sheila Rondeau. The race will commencing at 10:00  a.m. sharp

There will be a lunch break of one hour between the beginners and advanced divisions. Ribbons will be awarded after each division race with the Ultimate Cowboy Triple Crown Challenge awards being awarded at the very end of the day!!! We hope you can all stay for the final awards ceremony. 

The address for the Norfolk County Fair is 172 South Drive Simcoe Ontario. The easiest entrance  to navigate with trailers is located on Queen Street and the exit is on Evergreen Hill Road. 

The Ultimate Cowboy Challenge is a rain or shine event so please come prepared for all weather conditions. 

The current course is set up at  Second Chance Ranch for anyone to practice and will be open until Saturday (October 12th) evening!! 

If you have any questions or concerns please don't hesitate to contact any of our amazing Ultimate Cowboy Challenge organizers. 

Confirmed dates for 2019

Saturday, August 10, 2019


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Saturday, September 21, 2019


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Monday, October 14, 2019


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To Our Generous Sponsors & Supporters

          A new year; like a clean slate, brings excitement, unbridled potential, hope  and  2019 is no exception. It also provides us with an opportunity to reflect upon the year gone by and all the things we accomplished, obstacles overcome and new friends made.  The Ultimate Cowboy Challenge would like to take the opportunity to sincerely thank everyone who helped to make the 2018 Ultimate Cowboy ~ Triple Crown Challenge so extremely successful. From our organizers, venues, local fairs, volunteers, spectators and exhibitors  we THANK YOU!!

         We would also like to pay special thanks those who sponsor us particularly: Mike Yarek Dodge Chrysler Ltd in Paris, The Rope Shop, R.M. Nelles & Son, Great Lakes Realty, AMA Roofing Supplies, At Work Office Interiors, G.S. Wark Limited, Golden Horseshoe Beekeepers Association, Ghost Hollow Tack Shop, Redman Transportation and Myron Dudych Trucking.  Everyone associated with the Ultimate Cowboy Challenge genuinely thanks you for your generous sponsorship.  We would not be able to continue to put on such excellent local equine events without the on-going and continued support that these local companies, families and individual provide. 



There's much to see here. So, take your time, look around. We hope you enjoy our site and  feel drop us a line anytime at ULTIMATECOWBOYCHALLENGE@GMAIL.COM

The Gamblers Choice

Congratulations to all of our Gamblers Choice competitors and Winners ~ We look forward to seeing everyone for another exciting year of Ultimate Cowboy Challenges in 2019.