Trail Running calendar near Brookfield 2025-2026

Run or walk the Howl o'ween 5k at Busse Woods for a festive Halloween celebration that supports animal charities. Costumes and dogs are welcome on the flat paved course, with shirts, medals and finish treats for humans and pups.

Among the Trees on Oct 25 in Dousman WI invites trail runners to tackle 50k or 100k routes on Scuppernong and Ice Age Trail loops. Finishers get to brand a wooden medal with optional finish time for a memorable keepsake.

Energetic community races at the Momemtum Fall Classic in Janesville on October 25, 2025. Choose a 1 mile or a scenic three loop 5k on Optimist Community Park trails with proceeds supporting Momentum Track and Cross Country Club.

Join the ERC John Hennelly Public Cross Country Races at Lovelace Park in Evanston on October 26 2025. Community, open and masters races run a three lap 3.5 mile course across hills and fields. Teams and all ages welcome rain or shine.

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.

Join the Warrior 5K & 8K Through The Park on November 8, 2025 in Greenfield Park, West Allis. Enjoy scenic rolling trails, team or solo races, and postrace treats while supporting Wisconsin Lutheran College and a local charity.

Event details The Big Timber XC Challenge takes place Sunday, November 9, 2025 at Camp Big Timber, Big Timber Road at Tyrrell Road, Elgin, Illinois. Distances offered: 3 miles - one loop of the perimeter trail 5 miles - two loops of the pe..

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.

Event overview The Fast Eddie 50k/5k takes place on Saturday, November 15, 2025, at Lapham Peak in Delafield, Wisconsin. The event includes the following distances: 50K 5K The location listed is W329 N, 846 County Trunk Hwy C, Delafield,..

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 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.

Conquer winter trails at the Frozen Gnome in Crystal Lake on January 10, 2026, a technical single track 10K loop repeated for the 50K or tackled in relays. Expect triple black diamond terrain, a Gnome Depot aid station, and a finisher medal..

Event overview The 50K MASHUP SLAM is a series of trail races in the Midwest based on the 50K distance. The series includes multiple events across the year, begins with the Frozen Gnome 50K in January and concludes in November with the Mine..

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..

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.