Milwaukee
Trail Running Calendar near Milwaukee 2026-2027
Explore the top trail runs near Milwaukee for 2026-2027! We've gathered 13 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.
A community fundraiser on October 10, 2026 at Petrifying Springs Park benefiting Rey de Reyes Ministry, with in-person trail distances and a virtual participation option.
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
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.