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.
November 2026
January 2027
Seven week evening ski series at Lapham Peak in Delafield with freestyle, classic and combo classes, nightly points and end of season awards.
11K freestyle and classical cross-country ski races at Lapham Peak with chip timing, age group awards, warming shelters, and proceeds for a snowmaking project.
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
A stair-climbing fundraiser on March 13, 2027 at 411 E Wisconsin Center in Milwaukee, featuring a 30-floor climb and a $100 per person fundraising minimum.
April 2027
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.
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 family friendly fundraiser on September 18, 2027 at Petrifying Springs Park with 1 mile and 2.25 mile routes and a virtual option supporting Rey de Reyes Ministry.
October 2027
Trail races at Scuppernong Trailhead in Kettle Moraine State Forest with 3.1, 5.4 and 10.8 mile loops plus a 19.3 mile combined option.