Cross country... the best of all human endeavors!

Get your winter-teammates together, grab your racing shoes/spikes, and join us for cross country racing over the tree-lined fields of Caldwell Woods and Bunker Hill forest preserves. For your adventure we will provide:

  • Traditionalists... your event distance choice of 5 Kilometers or 15 Kilometers.
  • Ultra consideration... our Gratuitous 6-Hour option for ultra runners with an 8:00 am starting time.
  • Space for ~150 eager runners... permit restrictions limit race participation to the first 150 registrants, which is a total combined count of participants within all events.
  • Colorful one-of-a-kind race shirts for all registered runners and volunteers.
  • Chip timing & scoring with instant results published here on for all participants.
  • Overall awards... presented to top male & female, open and masters.
  • Age division awards... 10-year age groups for both sexes, with depth determined by number of participants.
  • Team awards... for top teams based upon 3 scoring in 5 member teams.
  • Ultra awards... for those who tally more than 26.2 miles in our Gratuitous 6-Hour run.
  • Ultra Team awards... for top teams based upon 2 scoring with most accumulated mileage.
  • An accurately measured, clearly-marked course, with a with well-stocked aid station at the start / finish area.
  • Afterward... post-race celebration with fun and awards.

Winter Challenge Cross Country, Start / Finish area:
Caldwell Woods, Grove #1
6350 W Devon Ave, Chicago, IL 60646
GPS: 41.997615, -87.786481

Winter Challenge Cross Country is ideal for off-road/trail runners, and those experienced runners looking to compete with their teammates under cross country conditions. Our racecourse is designed as a 5-Km loop on grassy fields -but- may be rerouted to the paved trails should wintertime conditions dictate. Either way, participants can expect a clearly marked course -and- should be prepared for challenging seasonal conditions. Gratuitous 6-Hour runners will repeat the course for as many laps as they can, then may switch to a quarter-mile loop as the clock winds down from six hours -to- zero.

Upcoming Races

Jan 9 2022
6 Hours
Multiple Loop Course
1 Elevation Rating
Flat or nearly flat
2 Surface Rating
Mostly groomed trail or dirt roads


No Past Races
We try to keep the most accurate information about this race, but changes do happen. Always visit the official race website for the most up to date information. If you see an error, please let us know

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