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Trail Running Calendar near Delafield 2026-2027

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Explore the top trail runs near Delafield for 2026-2027! We've gathered 22 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Mixed four-person teams each run a 3000 meter leg in a USATF championship relay with Youth, High School, and Open divisions in Brookfield, WI.
Deer-themed race day at Nashotah Park with half marathon, 10K, 5K, ruck and family run options, and a wooden finisher medal for every finisher.
December 2026
Nighttime rails to trails event in Lake Mills, WI offering 17.5 mile and 31 mile out and back courses with cupless aid, required lights, and variable winter trail conditions.
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 event in Palmyra WI offering 100K, 50K and 10K loops on the Ice Age Trail with aid stations and required safety gear.
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
Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.
Trail series in Oconomowoc offering 5K, 10K, 13.1 mile, walk and ruck events from April to October 2027; registration opens October 16, 2026.
Seven trail races in the Kettle Moraine Forest near Eagle, Wisconsin running April 24 to October 16, 2027 with full series and per race registration options.
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.
Trail race at Palmyra Educational Learning Center with 4, 6.4 and 13.5 mile courses plus a combined Golden Gauntlet on the Ice Age Trail and cupless aid stations.
Trail event on May 29, 2027 at Scuppernong Trailhead offering 50K, 30K and 10K loops with a stocked aid station and a cupless policy.
June 2027
Trail races on the Ice Age Trail near Whitewater Wisconsin offering 10K, half marathon and 50K on rolling hills and varied singletrack.
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 mile trail ultramarathon along the Ice Age State Trail near Whitewater WI with nine aid stations, a 55 hour limit and mandatory FarOut offline maps.
October 2027
Timed 10 hour trail event at Alpine Valley, Elkhorn WI with clearly marked single track loops of 7, 14, 21 and 28 miles and optional weighted divisions.
Timed 6, 12 and 20 hour trail ultraruns in Eagle Wisconsin with solo and relay options across three loop distances and manual lap timing.
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