Trail Running calendar near Oconomowoc 2025-2026

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 on Nov 9 for team focused cross country excitement. Four person teams run 3000 meter legs in male female order for Wisconsin USATF titles and prizes.

Run the MacNider cross country course in Schaumburg on Nov 9 at the Fast Track Cross Country Open, with separate men's and women's races over a scenic 3.05 mile looped grass course. A great fall test for solo racers and teams alike.

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.

Run the Bucks & Does 13.1 Pointer through scenic wood chipped trails at Nashotah Park with a half marathon, 10K, 5K and a free Bambi Run for kids. All finishers receive a custom finisher woodle and can warm up with a free hot chocolate bar.

Run scenic trails at the Abominable Trail Race in Lake Geneva on November 15 with 5K, 15K and 30K distances plus team relay. Celebrate at Base Camp with live music, food trucks, local beer and cozy fire pits.

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.

Join the Winnetka Turkey Trot on Thanksgiving morning for a fun 5k on the Green Bay Trail with Family Trot and Speedy Trotters divisions and a rolling start. Festive vibes, kids get #1 medal and proceeds support local charities.

Join the Brooks Midwest XC Championships on Nov 29, 2025 at UW Parkside in Kenosha, WI. Multiple races award medals and offer a shot to qualify for the Brooks XC Championships in San Diego.

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.

Take on the Whitewalker Ultra 100k in Palmyra WI, a two loop 100k over scenic Ice Age Trail and Scuppernong trails. Expect rugged single track, aid stations on course, and a 24 hour finish limit for a true winter challenge.

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..

Join the ARKTOS winter ultra in Dousman, WI, a looped trail challenge where you run as many laps as you can in 6 hour, 12 hour or 20 hour windows. Solo and relay teams enjoy warming shelters, hot drinks and a post race meal.

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

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.

Run under the stars at Moonlight Meltdown on April 25 in Belgium WI, with chip timed 5k road and a Sunset Safari 10k including a trail through Harrington Beach State Park. Shirts, post race food and a finish party at KYOTES.