The 2024 Dick Pond Athletics Darn Tough Race Trail Series 

Every year, Dick Pond Athletics hosts a four-part trail race series to bring together runners across the Chicagoland area to divert from road running and hit the trails for a unique racing experience. 

In 2024, we are proud to be partnering with Darn Tough Vermont Socks for this year’s race series, announcing the race series to officially be named the “Dick Pond Athletics- Darn Tough Trail Race Series”. A brand synonymous with outdoors and trail running, Darn Tough embodies the sprit and toughness of our running community. 

Whether you run one race or all four, we are excited to have you be part of our trail race series. Finishers of all four racers will receive a bonus premium swag item at the end of the year! Are you darn tough enough to finish all four? 

History of the Trail Race Series 

The roots of the Dick Pond Athletics Trail Race Series originate from the Windmill Trail Challenge held in November 2018 where Brent Runzel suggested Dick Pond Athletics “should sponsor a race there” in an off-hand comment. With an enthusiastic “let’s do it!”, the vision became a reality. This first event exceeded expectations with more than 150 participants across the 5k and 10k distances.

In 2019, the first annual Big Timber XC Challenge was held at Camp Big Timber, after the forest preserve that hosted the Windmill Trail Challenge initially denied a permit for the race. The second Big Timber XC Challenge was held in November 2020 that was highly popular despite waves of the COVID pandemic. 

This sparked the discussion to hold a race in the Spring, which prompted the first Hickory Knolls 5k/10k Trail Run in May 2021. As popularity continued to grow so did the races, hosting the first Summer Trail Classic in August 2022 and Chauncey’s 4 at The Farm in March 2023. 

Thus, the full Dick Pond Athletics Trail Run Series was born! Join us on the trails in 2024! 

Chauncey’s 4 at the Farm – April 7, 2024 

In our first race of the year, we return to historic St. James Farm in Winfield, IL. In this race, we cover a one-loop, 4-mile course over gently rolling terrain, ideal for all runners and walkers. So come frolic over the prairie and through the woodlands on the wide limestone and mowed grass trails. 

Chauncey McCormick, the original owner of the property in 1920 and where the race got its name, would ride horses around the grounds. The St. James Farm Forest Preserve is a spectacular and spacious location to celebrate winter’s retreat and the arrival of Spring. 

This race took place on April 7 with an amazing group of runners. Special thanks to our race sponsor, New Balance! We hope to see you next year! 

Hickory Knoll Train Run & Relay – June 9, 2024 

Our second of four races brings us back to the trails of the Hickory Knolls Nature Area in St. Charles for the 4th annual trail run and relay. Participate in either the 5k or 10k distances, or join a friend in the 10k relay option. 

Join us as we run the grass and dirt trails over a 3-mile loop course through a beautifully diverse natural area. The course starts out relatively flat while a few hills await runners in the latter portion of the loop. The trail is wide, allowing for plenty of room for passing or camaraderie. All race distances are approximate.

Mark your calendar for June 9, 2024 and register now! We would like to send a special thank you to our race sponsor, Brooks! 

The week following the run, we will be hosting a free Brew Run at Pollyanna Brewing on June 11. RSVP today! 

Summer Classic Trail Run – August 18, 2024 

The third of four events in our series will take place on August 18, 2024. Come explore the twisting and turning single-track trails of Paul Douglas Forest Preserve in Hoffman Estates with us. 

Choose from three different distances (mileage is approximate): 

•5.5 miles (one loop) 

•10.5 miles (two loops)

•15.5 miles (three loops) 

Join us for a true trail running experience! Register today

The brew run for this race will take place on August 21 at Pollyanna Brewing. 

Big Timber XC Challenge – November 3, 2024 

Cap off the year with an autumnal romp through the woods - and the creek! - at the 6th annual 5k and 5-mile race. Stick around for a Pancake Breakfast put on by local Boy Scout Troop 60. It's a great way to finish off another year in trail running. 

The course consists of grass, gravel, dirt, possibly some mud, and of course, the beloved creek crossing around and through a natural wooded area. 

You can choose to participate in either the: 

  • 3-mile Run & Walk (one loop) 
  • or the 5-miles Run (two loops) 

There is also a Kids Fun Run, allowing youngsters 10 years and younger to join the fun. The Kids Fun run is on grass and does NOT cross the creek. 

Registration opens August 9! Thank you to our sponsor for this race, Saucony! 

Our final brew run will take place on November 5 at Pollyanna Brewing. 

Participate in our Trail Race Series 

Shake up your race routine this year and join us for any or all of our trail adventures that lay ahead. No matter if you’re a walker, runner, or run/walker, we welcome you to our race series. Grab a friend, plan your race calendar, and experience these beautiful runs in natural surroundings. We are excited to see you participate in the Dick Pond Athletics Darn Tough Trail Race Series!