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 at 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 races are great for folks wanting to get off the roads and enjoy some of our beautiful trails, without having to be an expert trail runner to reach the finish. They are laid back and fun for the entire family, and suit people of all ages and abilities looking to change up their running routine.
We will be headed back to Wolf Road Woods, part of the Palos Trail System, for our legendary USOLE 4 mile course, which runners complete twice for the 8 mile race. Runners who don't want to go 8 miles can compete in the one loop, 4 mile trail race instead. The course has a great mix of double and single track along with undulating terrain, and it may have a small hill or two to climb. USOLE Trail Challenge races are a great way to see the trails, get your long run and enjoy camaraderie with your trail running friends.
Distance: 4 Miles
Starts: Sat, Nov 21 · 10:00 AM
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!
Distance: 8 Miles
Starts: Sat, Nov 21 · 10:00 AM
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!
Willow Springs is a village in Cook County, Illinois, United States, with a small portion extending into DuPage County. It was founded in 1892 and named for the springs along the Des Plaines River, and it had a population of 5,857 in 2020. Summers are hot and winters are cold, so spring and early autumn are the best seasons to race.
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