Jackson
Trail Running Calendar near Jackson 2026-2027
Explore the top trail runs near Jackson for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
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, Wisconsin offering 5K, 10K, 13.1 Miles, ruck and walk events; registration opens October 16, 2026 and fee is $165.
June 2027
Weekend hikes in Northern Kettle Moraine State Forest with 20 mile and 30 mile single-loop courses, aid stations, certificates, parking, and finisher medals.
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.