Trail Running calendar near Waukesha 2025-2026

Frozen Gnome on Jan 10, 2026 in Crystal Lake, Illinois is a winter trail challenge through Veteran Acres and Sterne’s Woods with 10K, a Triple Black Diamond 50K and team relays. Expect hot aid, a tech shirt and finisher medal.

Kick off your trail season in Crystal Lake with the 50K MASHUP SLAM on January 10, 2026. Join a Midwest series of challenging 50K and 53K races that reward cumulative finish times and finisher buckles.

Take on the Whitewalker Ultra 100k at Emma Carlin in Palmyra WI on Jan 17 and 18, 2026, with two scenic 50k loops through Ice Age and Scuppernong trails. Enjoy staffed aid stations and 24 hours to finish this memorable winter trail challeng..

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

Tackle the Fox Valley Winter Challenge 5K at Dick Young Forest Preserve, the first of a three race trail series that may feature snow, slush or mud. Finishers get a medal and single race entrants receive a cozy winter hat.

Chill out and race the Frozen Tundra IPA 5K along the Des Plaines River Trail in Lincolnshire, then warm up at a lively post race party at Half Day Brewing with beer, food and prizes. Limited to 300 spots so register early.

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 Trail Series 8K in Aurora on Feb 21, the middle race on a scenic but wintry trail with woods, open paths and possible snow or mud. All finishers get a medal and single race participants receive a cozy win..

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

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.

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

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.

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 on April 18 at Veterans Acres in Crystal Lake with scenic single track trails and rolling hills, choosing from 50K, 15 mile or 5 mile distances. Enjoy a big aid station with homemade snacks and bring a reusable bottle.

Childish Nonsense is a playful trail race each late April at Deer Grove Forest Preserve West in Palatine, Illinois. Distances from 10K to 50 mile cover rolling crushed gravel loops with a friendly community vibe and plenty of shenanigans.

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.

Take on the Donald Dash Trail Run on May 2, 2026 at Donald County Park in Mount Horeb, WI with scenic 5 km and 15 km options over prairie, single track, sand and hills. Limited to about 300 runners, all proceeds fund Friends of Donald Park..

Run the Great Western Half Marathon and 10K on a flat out and back limestone path along the historic Great Western Trail. Hosted by Fox River Trail Runners, this longtime race supports local mental health charities.