Dick Pond Athletics and Darn Tough Vermont Socks are partnering together once again in 2025 to host the four-part trail race circuit, the Dick Pond Athletics Darn Tough Trail Race Series. This series brings together runners from across the Chicagoland area to participate in an offroad adventure and hit the trails for a unique racing experience.
Whether you run one race or all four, we are excited to have you be part of our trail race series. No matter if you are a long-time trail runner or a novice, you’re sure to enjoy the beautiful scenery at each of the race locations. We want to know – are you darn tough enough to finish all four?
Learn more about each of the races below.
New This Year – Register for the Entire Race Series by March 30, 2025
If you’re aching to get all four races in, you can register now for the ENTIRE series all at once for a discounted price. That’s four events, race-official swag and a finisher award for each individual race. PLUS, by running all four events, you receive a premium series swag, all for less than $44 per event.
The four events include:
- Chauncey’s 4 at the Farm – March 30 in Winfield, IL
- Hickory Knolls Trail Run & Relay – June 8 in St. Charles, IL
- DPA Summer Classic – August 24 in Hoffman Estates, IL
- Big Timber XC Challenge – November 9 in Elgin, IL
Sign up today to register for all four races, secure your premium swag, and get miles of dedicated trails. Scroll down to “Series Registration” to begin.
Chauncey’s 4 at the Farm – March 30, 2025
Kicking off the 2025 series, we head to the historic St. James Farm in Winfield, IL. This 4-mile race is one loop and covers gently rolling terrain, ideal for all runners and walkers. Come frolic over the prairie and through the woodlands on the wide limestone and mowed grass trails.
Registration for this race is now open, so mark your calendar and sign up today! Special thanks to our race sponsor, New Balance! We hope to see you next year!
Hickory Knolls Train Run & Relay – June 8, 2025
Our second race in the series 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 distance or join a friend in the 10k relay option.
This race covers grass and dirt trails over a 3-mile loop through a beautifully diverse natural area. The course starts out 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 8, 2025 and register now!
Special thanks to the sponsor of Hickory Knolls, Brooks Running!
Summer Classic Trail Run – August 24, 2025
Our third event in the series lets you explore the twisting and turning single-track trails of Paul Douglas Forest Preserve in Hoffman Estates with us. Don’t worry about the August sun and heat, this terrain is predominantly flat with the majority of the trails well shaded.
As new trails open in this preserve, we are exploring a variety of route options and distances to choose from. Stay tuned to this blog and the Dick Pond Athletics Facebook page for registration and distance information.
Join us for a true trail running experience! Registration opens soon – we hope to see you on the trails.
Big Timber XC Challenge – November 9, 2025
Cap off the year with an autumnal romp through the woods - and the creek! - at the 7th annual 5k run/walk and 5-mile run at Camp Big Timber in Elgin, IL. The Big Timber XC Challenge is known for its flannel shirt swag, the Ranger’s Revenge, and the legendary creek crossing. And don’t forget about the post-race Pancake Breakfast put on by local Boy Scout Troop 60! It's a great way to finish off another year of trail running.
The course consists of grass, gravel, dirt, and possibly some mud, and of course, the beloved creek crossing around and through a natural wooded area.
Registration opens soon to be sure to stay tuned!
Participate in our Trail Race Series
Are you darn tough enough to take on this trail race series? Shake up your race routine and join us for any or all of our trail adventures that lay ahead. No matter if you’re a walker, runner, or anywhere in between, 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!
