Trail Running calendar near Williams Bay 2026-2027

On February 7, 2026 join the Frozen Assets 5K in Madison and run or skate across the frozen surface of Lake Mendota, starting and finishing at The Edgewater. Enjoy scenic views of downtown and the UW Madison campus during the Frozen Assets..

An 8K winter trail race at Oakhurst Forest Preserve on February 21, 2026. The course starts with a steep sledding hill and may include snow, ice, or mud, with finish-line water, snacks, and a finisher medal.

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

Trail races at The Forge in Lemont offer a wooded course around the Lemont Quarries with a half and quarter marathon on single and double track. Varied terrain includes gravel, rocks, mud and short technical climbs; trail shoes and personal..

Run with your dog through scenic wooded single track at Lake Geneva Ziplines, choosing a 4 mile loop or an 8 mile double lap. This friendly canicross event offers water at the start area, prizes for top teams, and a finisher token.

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles on March 22, 2026. Final event of a three race winter series with mixed terrain, finish line water and snacks, and finisher medals plus winter gear for series finishers.

Timed loop trail races at Lowell Park in Dixon, IL include 33.75-mile and 13.5-mile options plus a relay. Single track loops alternate direction each lap and a staffed aid station provides drinks and snacks.

Tackle a scenic 4 mile loop through rolling limestone and wooded trails at St James Farm in Warrenville, IL, with roots, mud and natural single loop terrain. Enjoy a long sleeve race shirt, wood finisher medallion and lively race day atmosp..

Trailbreaker in Waukesha on March 29, 2026 offers marathon, half, 10K, 5K, walk, ruck events, a Kiddos 1K, and The RAD, with proceeds supporting the Park Foundation and courses on local trails including the Glacial Drumlin.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

Trail races in Crystal Lake, Illinois on a roughly five mile loop through single track and mixed woods. Distances include 50K, 15 Mile and 5 Mile with one main aid station, an eight hour cutoff, and age group awards.

A looped trail race at Deer Grove Forest Preserve near Palatine, IL offering 10K, 25K, 50K and 50 mile options on soft gravel loops with a single aid station per lap and inclusive entry policies.

Join Moonlight Meltdown and Sunset Safari in Belgium, Wisconsin for a flat, well lit 5k or a scenic 10k into Harrington Beach State Park. Chip timing, shirts and refreshments raise funds for Belgium Fire and Rescue and local youth programs.

A Batavia fundraiser for Anderson Humane featuring a timed 5K and a 1.5 mile community walk around the Batavia Riverwalk; proceeds support shelter, medical care, and wildlife rescue.

Run the Donald Dash Trail Run at Donald County Park in Mount Horeb on May 2, 2026 for scenic prairie, sandy and hilly single track trails and distances of 5 km, 15 km and a Kids One Mile Fun Run. All net proceeds fund Friends of Donald Park..

A flat out and back half marathon and 10K along the limestone Great Western Trail on May 3, 2026, hosted by Fox River Trail Runners. Registration contributions support three local mental health charities.

A trail marathon and a 10 mile race at Teason's Woods in Palos Hills on May 9, 2026, using the Sag Valley Trail. Wide horse trails, multiple aid stations, pre assigned race day packet pickup, and a unique wooden finisher medal.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

A trail event in Delafield, Wisconsin offering half marathon, 10K, 5K, ruck options and a Kiddos 1K; proceeds benefit Tall Pines Conservancy and courses use marked park trails.