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
A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding 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.
One of the oldest continuously running ultras in the country, Ice Age Trail 50 runs through glacial terrain and offers 50 mile, 50K and half marathon distances.
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.