The USOLE November Trail Challenge The Ryan & Katie Flynn 8 Mile (2 loop Course) We will offer an option to race one loop with a 4 mile distance (1-loop)

November 21, 2026 @ 10AM Trail running has always been in our USOLE DNA! We were the first running store in Chicago to bring trail racing to the Chicago running community. These trail races are great courses for folks wanting to get off the roads and enjoy some of our beautiful trails, but not have to be an expert trail runner to get to the finish. Our trail races are very laid back and great fun for the entire family, making it fun & easy for all! The USOLE Trail Challenge is great for people of all ages and all abilities looking to change up the running routine and get “off” the roads!

Trail Race Location: We will be headed back to Wolf Road Woods, part of the Palos Trail System to tackle our legendary USOLE 4 mile course (will do this loop twice for the 8 mile race). We will offer runners who don't want to go 8 miles a chance to compete in the ONE loop, 4 mile trail race if they choose. This course will have a great mix of double & single track along with undulating terrain in the beautiful Wolf Road Woods! It may have a small hill or two to climb as well, but fun will always be had! USOLE Trail Challenge races are a great way to see the trails, get your long run and enjoy camaraderie with your trail running friends!

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Distances

4.0 mi

8.0 mi