Oconomowoc
Trail Running Calendar near Oconomowoc 2026-2027
Explore the top trail runs near Oconomowoc for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
Multi-distance trail event in the Southern Kettle Moraine State Forest offering 200M, 150M, 100M, 50M, 50K and a 15K fun run; proceeds fund forest projects.
Multiple distances at Fort Atkinson High School including a 12K mixed-terrain course, a 5K through neighborhood streets, and a 1-mile fun walk/run.
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
Four-person mixed relay with each runner completing a 3000 meter leg in Brookfield WI serving as the Wisconsin USATF Association Mixed Relay Championships.
December 2026
Nighttime rails-to-trails event in Lake Mills with 31 miler and 17.5 miler options, required lights and reflective gear, and staffed aid at turnarounds.
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.
January 2027
Winter trail ultramarathon near Palmyra, WI offering a two loop 100K and a new single 50K loop on Ice Age, Whitewater and Scuppernong trails.
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
Trail series in Oconomowoc offering 5K, 10K, 13.1 mile, walk and ruck events from April to October 2027; registration opens October 16, 2026.
May 2027
Multi-duration ultrarun in Kettle Moraine State Forest with three loop options, Jackpot prizes for 24-hour solo and relay, on-site camping, and event-specific swag.
Historic Wisconsin trail ultramarathon on glacial terrain offering 50 miles, 50K and a half marathon; registration opens December 13, 2026.
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 136 Miler on the Ice Age State Trail near Whitewater WI on Sep 24 2027 with nine aid stations, required FarOut offline maps, and defined pacer and crew rules.
October 2027
A 10-hour endurance walking challenge at Alpine Valley Resort in Elkhorn, WI with 7, 14, 21 or 28 mile options and optional weighted rucks.