Trail Running calendar near Richmond Township 2026-2027

An ultrarunning event in Kettle Moraine State Forest on May 2–3, 2026 offering 6 hour, 12 hour and 24 hour solo and relay formats across three loop lengths. Jackpot cash prizes are funded from registration fees and distributed to top finish..

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

Experience the Three Ravines Course at Wolf Road Woods with distance options of 3.1 or 5.4 miles. This family friendly trail event features a mix of single track terrain and a post race celebration with craft brews.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

Trail marathon and 10 mile on the Sag Valley Trail at Teason's Woods featuring substantial elevation, multiple aid stations, sunflower shirts and wooden finisher sunflowers, plus post race chili, beer and awards.

A long running Wisconsin trail ultramarathon that winds through forests, rocky ridges and glacial landforms. The event offers 50 miles, 50K and a half marathon and typically sells out quickly.

A timed endurance trail event near Willow Springs on a 4 mile loop with single and double track, rolling hills, a signature aid station offering snacks and drinks, and a mandatory reusable cup policy.

A low-impact, no-frills running event in Delafield, WI that highlights Lapham Peak State Park and raises funds for Tall Pines Conservancy. Races range from a Half Marathon to a free kids 1K.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

Big Climb Wisconsin on May 16, 2026 in Madison is a team-based stadium climb that features stairs, ramps, and concourses. The event honors patients and survivors and awards participants a finisher medal while supporting efforts against bloo..

A chip timed *10K* trail run at The Forge Lemont Quarries featuring mostly crushed limestone surfaces, wooded scenery, competitive overall and age group awards, and a 450 participant capacity.

Rail-trail event in Belleville, WI using the Badger State Trail and Sugar River State Trail. Distances include 50 miles, 50K and a half marathon on flat, soft surfaces with trestle bridges and a quarter mile tunnel.

Frontline OCR at Byron Motosports Park on May 23, 2026 offers 10K and 5K obstacle courses, a ruck division, a kids mile, Special Forces and Heroes waves, plus team entry packs, organized by a 501(c)(3) foundation.

A one-day community running festival in Crystal Lake, IL, featuring group runs of 4.3 or 6.8 miles, an expo with vendors and run clubs, food for purchase, and a raffle.

Experience an inclusive trail running event at Richard Bong State Recreation Area. Choose from five different timed options ranging from three to twenty four hours on a scenic course with rolling hills.

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

A community 5K on June 6, 2026 in Joliet along the Rock Run Greenway Trail with start and finish at Cemeno's Pizza. Proceeds benefit the Pat Clark Cancer Foundation to support local cancer patients and families.

Trail race at Hickory Knolls Nature Area in St Charles with 5K, 10K, and a 2 person 10K relay on June 7 2026. The course runs on dirt, grass and gravel paths with marked loops and limited on course water.

An annual June endurance trail event featuring 100 mile, 100k, 50k and 38 mile options on mainly Ice Age Trail terrain. Entry for 2026 is by lottery with an ordered waitlist and early invites for rollovers and volunteers.