Trail Running calendar near Oconomowoc 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..

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..

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..

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.

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..

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

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.

Run the Sugar Badger 50/50 and Half in Belleville WI with 50M, 50K and half marathon options on flat, scenic Badger and Sugar River trails with trestles and a short tunnel. Aid, free photos, pizza and beer await finishers.

Free one day running festival in Crystal Lake celebrating local races, clubs, and brands. Pick a 4.3 or 6.8 mile social run, browse the expo, enter raffles, demo gear, and enjoy food, drinks and community fun.

Kettle Moraine Ultramarathon in La Grange WI on June 13 and 14, 2026 showcases rugged, scenic trails with about 65 miles on the Ice Age Trail. Distances from 38 to 100 mile plus 100K and a 4 person relay; 100 mile offers a Western States qu..

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 14 June 2026. You can run between 5 and 21 kilometers.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 27 June 2026. You can run between 5 and 21 kilometers.