Williams Bay
Trail Running Calendar near Williams Bay 2026-2027
Explore the top trail runs near Williams Bay 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.
October 2026
Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.
Trail race in Crystal Lake, Illinois on October 17, 2026 featuring single track forest loops with 5 and 10 mile options and race shirts plus finisher medals.
Runs at Richardson Adventure Farm in Spring Grove include a 10K, a corn maze 5K with over 250 turns, a farm 5K, and a kids 1 mile.
October running event at Optimist Community Park in Janesville offering 1 mile and 5K courses with proceeds to Momentum Track and Cross Country Club.
November 2026
Multi-distance trail event in the Southern Kettle Moraine State Forest offering 200M, 150M, 100M, 50M, 50K and a 15K fun run; proceeds fund forest projects.
Multiple distances at Fort Atkinson High School including a 12K mixed-terrain course, a 5K through neighborhood streets, and a 1-mile fun walk/run.
A trail event at Pringle Nature Center on November 7, 2026 offering a 5K run and 2 mile walk with fees supporting environmental education.
Trail race at Lake Geneva Ziplines & Adventures offering 5K, 10K, 15K and a 30K solo or team relay with chip timing and free race photos.
December 2026
A trail event in Lake Geneva focused on Canicross and dog-friendly running, offering 4 mile loops or two loops for 8 miles on technical singletrack.
January 2027
Winter trail race in Crystal Lake, IL featuring a hilly single-track 10K loop and a 50K made of five laps, with aid stations, finisher medals, and age-group awards.
Winter trail ultramarathon near Palmyra, WI offering a two loop 100K and a new single 50K loop on Ice Age, Whitewater and Scuppernong trails.
A winter obstacle race in Lake Geneva with kids courses, fun runs, a 20K Yeti challenge, and a competitive 10K offering cash prizes and age group awards.
April 2027
Trail races in Crystal Lake, Illinois offering 50k, 15 mile and 5 mile distances on a 5.2 mile loop through single track, prairie and pine forest.
May 2027
Nighttime obstacle race in Pingree Grove, IL with multiple 5K heats and a 30K unlimited laps option, illuminated obstacles, live entertainment, and onsite parking.
Historic Wisconsin trail ultramarathon on glacial terrain offering 50 miles, 50K and a half marathon; registration opens December 13, 2026.
July 2027
Kishwauketoe 5K Run / Walk in Williams Bay featured a 5K and a quarter mile kids run, with 280 finishers and community volunteers restoring trails after a storm.
August 2027
A Scottish Highlander themed obstacle race in Pingree Grove on August 7, 2027 offering 50K, 15K, 5K, family 3K, a torch lit night run and a haunted 5K.
Test your teamwork at Richardson Adventure Farm with 5 km, 15 km, or multi-lap Infinity courses featuring iconic obstacles and varied terrain.