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Trail Running Calendar near Brookfield 2026-2027

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Explore the top trail runs near Brookfield 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
Trail ultras of 100k and 50k through the Southern Kettle Moraine Forest on the Ice Age Trail with aid stations and on site wooden medal branding.
November 2026
Trail runs and a 2.25 mile walk through rolling park trails and wooded sections in West Allis.
Four-person mixed relay with each runner completing a 3000 meter leg in Brookfield WI serving as the Wisconsin USATF Association Mixed Relay Championships.
Bucks & Does 13.1 Pointer is a multi-distance running, walking, and ruck event at Nashotah Park on 11/14/2026. Distances range from a youth Bambi Run to a 13.1 Pointer, and every finisher receives a wooden finisher medal.
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.
January 2027
Winter trail ultramarathon near Palmyra, WI offering a two loop 100K and a new single 50K loop on Ice Age, Whitewater and Scuppernong trails.
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
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.
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 races at Scuppernong Trailhead in Dousman, WI offering 50K, 30K and 10K on a 10K+ loop with an aid station, cupless policy, and proceeds supporting Kettle Moraine projects.
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.
October 2027
A 10-hour endurance walking challenge at Alpine Valley Resort in Elkhorn, WI with 7, 14, 21 or 28 mile options and optional weighted rucks.
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