Trail Running calendar near Lake County 2025-2026

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

Challenge yourself at Save the Drama for your Llama, a six hour trail run at Luhr County Park in La Porte IN on April 4, 2026. Run as many 1.7 mile loops as you can and aim to cover the most miles to win overall.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 11 April 2026. You can run between 5 and 10 kilometers.

Join the Earth Day trail run at Veterans Acres in Crystal Lake offering 50K, 15 mile and 5 mile options on a rolling 5 mile single track loop around the pond. Enjoy homemade aid station treats and a friendly, eco minded race atmosphere.

Run 10K, 25K, 50K or 50 Miler loops at Deer Grove Forest Preserve West in Palatine. Mostly wide non technical trails, a single aid station, pacers allowed for 50 Miler after four loops, and on course shenanigans promise a fun day.

Run scenic trails at Teason's Woods in Palos Hills on May 9, 2026 with marathon or 10 Mile options over rolling terrain and shared two way trails. Enjoy event apparel, a wooden sunflower medal for finishers, plus post race chili and beer.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 10 May 2026. You can run between 5 and 10 kilometers.

Join the JH Memorial 5 Mile Trail Run on May 25, 2026 at Stoney Run Park for a rugged trail with marked turns, a water station, and an optional pond crossing. Finishers receive snacks, medals for top places, and a free water bottle.

Kettle Moraine returns June 13 and 14 2026 in LaGrange Wisconsin, offering 100 mile, 100K and shorter trail distances with plenty of Ice Age Trail scenery. The 100 mile serves as a Western States qualifier, making this a prime summer ultra.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 14 June 2026. You can run between 5 and 10 kilometers.

Take on rolling hills and changing trail footing along a scenic Ice Age Trail section at Rice Lake Nature Trail in Whitewater, WI on June 20, 2026. Choose 10K, half marathon or 50K for a rewarding summer trail challenge.

Join DBC Gifts of Love Community 5K in Flossmoor on June 20, 2026, for a scenic 5K at Vollmer Road Grove Forest Preserve or run the Virtual 5K. Help send backpacks, school supplies and gift cards to local homeless students.

Run the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K or 10M loop courses and relay teams. Unique golf style scoring by Hole turns every loop into a strategic race that rewards speed and smart pacing.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 27 June 2026. You can run between 5 and 10 kilometers.

Tackle scenic single track and winding trails at the Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 4, 9, and 18 mile options. Enjoy creek crossings, farmland views and a friendly post race gathering for all finishers.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 1 August 2026. You can run between 5 and 10 kilometers.

Run trails, sand dunes and waterfront streets at the Mt Baldhead Challenge in Saugatuck on September 12, 2026. Choose a 10K or half marathon with a 302 step climb to the summit and timed staggered starts; proceeds benefit local youth.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 19 September 2026. You can run between 5 and 10 kilometers.

The Echo 136 is a 136 mile trail ultramarathon through the scenic Kettle Moraine and Ice Age State Trail near Whitewater, Wisconsin on September 25, 2026. Expect rugged singletrack, generous aid stations and a 55 hour time limit.

Run scenic loops through Tryon Farm's grassy fields and single track trails while supporting the Tryon Farm Institute. Choose distances from a 2 mile fun run up to a challenging 50k in this inclusive Crazy Legs Race Series event.