Trail Running calendar near Waukesha 2025-2026

Join the Bristol Woods Trail Run at Pringle Nature Center for a scenic 5K and a 2 mile hike through beautiful wooded trails. Held the first Saturday in November, proceeds support environmental education at Pringle Nature Center.

Hit the trails at Elver Park on Saturday November 1 for a family friendly event offering 10K, 5K and a free kids 1K. Finish by the main shelter, enjoy a post race raffle and friendly community vibes.

Run the Warrior 5K or 8K at Greenfield Park in West Allis. Scenic wooded trails, team and individual entries, shirts, awards and post race snacks. Proceeds benefit Wisconsin Lutheran College and a local charity.

Join the PRO Mixed XC Relay at Mitchell Park in Brookfield on Nov 9, a four leg mixed relay with each teammate running a 3K in male female male female order. Open to clubs and individuals with Youth, High School, Open and Masters divisions.

Run the Fast Track Cross Country Open in Schaumburg on Sunday November 9 with separate men and women races on a scenic 3.05 mile looped grass course. Open to all ages and abilities, teams are welcome.

Tackle rugged trails and a fun creek crossing at the Big Timber XC Challenge in Elgin. Choose 3 mile, 5 mile or a kids fun run, enjoy pancakes and a finisher woodallion, and support local youth organizations.

Join the Bucks & Does 13.1 Pointer on November 15, 2025 in Nashotah Park for scenic wood chip trail races including a half, 10K, 5K and a kids Bambi Run. Enjoy shaded paths, chip timing and a unique finisher woodle.

Join the Abominable Trail Race at LG Ziplines near Lake Geneva on November 15, 2025 for scenic 5K, 15K and 30K trail courses with individual and relay team options. Finishers get a medal, tee and a craft beer or hot cider.

Run the inaugural Fast Eddie 50K or the popular 5K at Lapham Peak, enjoying scenic woodland loops and rolling trails. All entry proceeds benefit the Little Warrior Foundation supporting children facing cancer.

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

Take on the 50K MASHUP SLAM, a Midwest trail series that spans eight scenic events and rewards runners who finish five races with a special finisher buckle. Top series placers earn awards at the final G.O.A.T.z or Miner 49'er event.

Challenge winter single track trails at Veteran Acres and Sterne's Woods in Crystal Lake on a triple black diamond course offering 50K, 10K and relays. The 50K is five laps of a 10K loop with a warm Gnome Depot serving hot food and coffee.

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second..

Tackle winter trails in the Fox Valley with a three part Challenge Series featuring a 5K in Batavia, 8K in Aurora and 10K in St Charles across Jan to Mar. Register single or as a bundle and earn upgraded swag for multiple races.

Run or skate across frozen Lake Mendota at the Frozen Assets 5K, starting and finishing at The Edgewater hotel. Enjoy skyline and UW campus views while taking part in a chilly festival favorite, with options for walkers, runners, and skater..

Take on ARKTOS Feb 28 to Mar 1 2026, a winter loop ultra in Wisconsin's Southern Kettle Moraine. Run solo or with a team of up to 4 in 6 Hour, 12 Hour or 20 Hour timed loops for cold weather challenge and community fun.

Trailbreaker : March 29, 2026, Waukesha, WI The Trailbreaker is scheduled for March 29, 2026, in Waukesha, WI, with the main venue at the Schuetze Recreation Center / Frame Park Baseball Stadium. The event has been hosted by the Park Founda..

Run the NK50k in Greenbush, Wisconsin on April 11, 2026. Choose 50K or 25K point to point routes across rolling ski tracks, rocky Ice Age Trail sections and lofty ridgelines, with aid stations, shuttle service and post run food; expect to b..

Join the Earth Day trail run at Veterans Acres in Crystal Lake offering 50K, 15 mile and 5 mile options on a rolling 5 mile single track loop around the pond. Enjoy homemade aid station treats and a friendly, eco minded race atmosphere.