Jackson
Trail Running Calendar near Jackson 2026-2027
Explore the top trail runs near Jackson for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
November 2026
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
Mixed four person relay in Brookfield WI with 3000 meter legs, division awards, USATF state championship status, and proceeds supporting the local high school cross country team.
December 2026
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.
March 2027
Stair climb fundraiser at 411 E Wisconsin Center in Milwaukee on March 13, 2027, supporting the American Lung Association with a $100 fundraising minimum.
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.
June 2027
Two-day hiking event in Northern Kettle Moraine State Forest with 20- and 30-mile single-circuit routes, aid stations, finisher medals, and on-site parking.
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.