Trail Running calendar near Whitewater 2026-2027

Run the Frozen Tundra IPA 5K along the Des Plaines River Trail, then warm up at Half Day Brewing with music, beer, hot toddies and food. Limited to 300 runners, entries include shirts, medals and a lively post race party.

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..

Run the Fox Valley Winter Challenge 8K on Feb 21 at Oakhurst Forest Preserve in Aurora, a mixed terrain winter trail with possible snow, ice, or mud. All finishers get a medal and completing the series earns bonus gear including a hooded zi..

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

Tour de Dodge is a scenic trail running festival at Governor Dodge State Park with 50K, 27K and 10K routes on March 7, 2026. Proceeds benefit local conservation and runners enjoy stocked aid stations, a custom shoe bag and horseshoe finishe..

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.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

Wrap up winter on scenic mixed trails at the Fox Valley Winter Challenge 10K in St. Charles on March 22, 2026. Expect varied footing, a finisher medal and cozy winter hat, plus bundle pricing if you tackled other series races.

Take on the Skunk Ape 806 314 Trail Race at Lowell Park with 33.75 mile and 13.5 mile solo options or a team 806 relay. Alternate wooded loops, enjoy hearty aid station fare and finisher swag, and chase podium awards and great camaraderie.

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 invites runners to scenic courses along Glacial Drumlin and Fox River trails, with distances from marathon to Kids 1K. New ruck events add variety while proceeds support local parks and the urban forest.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Take on a scenic point to point tour of the Northern Kettle Moraine Ice Age Trail in Greenbush, Wisconsin, on April 11. This supported, noncompetitive run offers 50K and 25K options with aid stations, drop bags, and finish refreshments.

Celebrate Earth Day at Crystal Lake with 50K, 15 Mile and 5 Mile trail options on a rolling 5 mile loop around the pond. Enjoy single track, a main aid station with homemade fuel and an eco friendly vibe.

Trail loops at Deer Grove Forest Preserve near Palatine, Illinois, with 10K, 25K, 50K and 50 Mile options on wide crushed-gravel paths. One aid station at the start and finish returns about every 5.5 miles.

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.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 10 May 2026. You can run between 5 and 21 kilometers.