Dick Pond Athletics and Darn Tough Vermont Socks are back again in 2026 partnering together 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 offroad adventures 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?
Register for the 2026 Entire Race Series by April 11
If you have a goal 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 premium series swag.
The four events include:
- Chauncey’s 4 at the Farm – April 11 in Warrenville, IL
- Hickory Knolls Trail Run & Relay – June 7 in St. Charles, IL
- DPA Summer Classic – August 23 in Hoffman Estates, IL
- Big Timber XC Challenge – November 8 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 – April 11, 2026
Kicking off the 2026 series, we head to the historic St. James Farm in Warrenville, 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!
Hickory Knolls Train Run & Relay – June 7, 2026
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 7, 2026 and register now!
Special thanks to the sponsor of Hickory Knolls, Brooks Running!
Summer Classic Trail Run – August 23, 2026
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.
Choose from three different distances - approximate 4 miles, 9.5 miles, and 13 miles, for a true trail running experience!
Thank you to our sponsor Mount to Coast!
Join us! Learn more and register now.
Big Timber XC Challenge – November 8, 2026
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.
Thank you to our sponsors, Saucony and Pollyanna Brewing!
Participate in our 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! Are you darn tough enough to take on this trail race series?
