Trail Running calendar near Rockford 2025-2026

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..

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 run at Deer Grove in Palatine offering distances from 10K to 50 miles on mostly smooth looped trails. Expect laps, an on course aid station, and plenty of shenanigans from the whimsical organizers.

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.

Run scenic horse and forest trails at Teason's Woods on May 9, 2026 with a 26.2 mile marathon or a 10 mile option. Finishers get a wooden medal and can refuel with hot chili and beer.

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

Run scenic flat trails along the Badger State and Sugar River in Belleville WI at the Sugar Badger 50 Miler, 50K and Half Marathon on May 23, 2026. Enjoy generous cutoffs, stocked aid stations, a quarter mile tunnel so bring a light, plus p..

Celebrate the 25th anniversary 5K for Double "J" in Joliet on June 6, 2026 as participants run the Rock Run Greenway and finish at Cemeno's. Proceeds support the Pat Clark Cancer Foundation and registration includes a T shirt and medal.

Challenge yourself on the scenic Kettle Moraine trails in LaGrange WI with distances from 38 miles to the full 100 miler and team relays. A largely Ice Age Trail course and Western States qualifying time make this a classic ultrarun.

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

Take on rolling hills and changing trail footing along a scenic Ice Age Trail section at Rice Lake Nature Trail in Whitewater, WI on June 20, 2026. Choose 10K, half marathon or 50K for a rewarding summer trail challenge.

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

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 1 August 2026. You can run between 5 and 21 kilometers.

Push your limits at Run The Hawk Trail Run in Middleton, WI, a timed challenge at Blackhawk Ski Club. Solo or team multi hour races and a fun run on a rugged loop with steep climbs, pines, a spring pool and a ski jump backdrop.

Run the GristMill Grind on September 5, 2026 at Franklin Creek State Natural Area, a hilly technical trail offering 5K and 10K routes through ravines, limestone bluffs, springs and creek crossings. Proceeds support park conservation.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 19 September 2026. You can run between 5 and 21 kilometers.

The Echo 136 is a 136 mile trail ultramarathon through the scenic Kettle Moraine and Ice Age State Trail near Whitewater, Wisconsin on September 25, 2026. Expect rugged singletrack, generous aid stations and a 55 hour time limit.

Run the Hennepin Hundred, an all trail ultramarathon along the scenic Hennepin Canal featuring flat terrain and canal and farmland views. Distances: 100, 50, 50K and team relay with Western States qualification for the 100.

Take in wooded trail views at the Fall Into Fall Trail 5k in Janesville, then stay for live music, food trucks and beer and wine tasting at the festival. Run or walk a fun, scenic course and celebrate the season with community festivities.