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
Trail running and a guided perimeter walk at Rock River Heritage County Park with a timed 5K using chip timing and a heritage celebration with food trucks and live music.
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 event in Crystal Lake offering 5 and 10 mile looped courses on single-track forest trails, with a race shirt and skeleton finisher medal.
A fall race at Richardson Adventure Farm in Spring Grove featuring 10K, two 5K options and a 1 mile family run through the corn maze with finisher medals for all.
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.
The 14th annual Frosty Rock Challenge in Fort Atkinson offers a 12k, a 5k and a free 1 mile walk run with proceeds supporting local and international Rotary projects.
A trail event at Pringle Nature Center on November 7, 2026 offering a 5K run and 2 mile walk with fees supporting environmental education.
On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.
December 2026
A dog-friendly Canicross event in Lake Geneva offering a 4 mile loop or an 8 mile option on winding single-track trails with on-course hydration and finisher items.
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.
Conquer a winter obstacle course in Lake Geneva with distances ranging from 5K to 20K plus a dedicated kids race and a festive basecamp with fire pits.
April 2027
Trail races in Crystal Lake, IL on a 5 mile loop offering 50K, 15 mile and 5 mile distances with an aid station and age group awards.
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
Experience the natural beauty of the Kishwauketoe Nature Conservancy in Williams Bay during this annual 5K and kids fun run held on the scenic trail system.
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.