Oconomowoc
Trail Running Calendar near Oconomowoc 2026-2027
Explore the top trail runs near Oconomowoc for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A community 5k and a 54 yard dash on October 4, 2026 in Glendale with an out-and-back course on the Oak Leaf Trail. Registration includes all-day entry to Milwaukee's Original Oktoberfest at Old Heidelberg Park.
Community running, rucking, and family walking event on October 10, 2026 in Oconomowoc, with proceeds supporting children with special needs.
Looped fundraising run and walk at Another Chance Ranch in Neosho, WI offering distances from a few miles to a marathon and beyond, with a $35 registration donation.
November 2026
A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.
The 14th annual Frosty Rock Challenge in Fort Atkinson offers a 12k, a 5k and a free 1 mile walk run with proceeds supporting local and international Rotary projects.
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
December 2026
Night-time out-and-back runs on a flat crushed limestone trail in Lake Mills WI, with approximately 17.5 and 31 mile options and required lights and reflective gear.
A progression run on a 443 m indoor track at Pettit National Ice Center on 12/26/2026 where pace increases every three laps until one runner remains.
February 2027
A winter timed ultra in the Southern Kettle Moraine Forest offering 6, 12 and 24 hour loop options for solo runners and relay teams. The field is limited to 160 participants and the 6 hour option is available in AM and PM waves.
April 2027
May 2027
One of the oldest continuously running ultras in the country, Ice Age Trail 50 runs through glacial terrain and offers 50 mile, 50K and half marathon distances.
August 2027
A 24 hour event at Nashotah Park with solo and relay options plus a range of fixed distance runs and ruck events, camping and evening activities.
Community run and walk at Kettle Moraine Lutheran High School featuring a two-loop 5 km, a 2 mile walk, and a 400 m kids run.
September 2027
A roughly 136 mile ultramarathon on the Ice Age Trail near Whitewater WI with nine aid stations, a 55 hour limit, required FarOut offline maps and specific pacer and crew rules.