Trail Running calendar near Monona 2026-2027

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

Timed ultraruns in Southern Kettle Moraine Forest on Oct 10 to Oct 11, 2026. Solo runners or teams of up to four complete as many 3, 5, or 6 mile McMiller Trail loops as possible in 6, 12 or 20 hour formats.

Trail ultra at Bethel Horizons in the Driftless Area offering 50K, 20M and 10M looped courses with mixed singletrack, grassy ridgelines, rocky climbs, fully stocked aid stations and chip timing.

Trail runs and a 1-mile walk at Fox Hill Nature Preserve on 10/11/2026, held to support conservation in the Cedar Lakes region; varied distances include 5K, 10K, a 1-mile walk, and a Kiddos 1K.

A Midwest trail ultramarathon in Dubuque that uses a roughly 20 mile loop through the Mines of Spain Recreation Area. Options include a 100 mile five loop race and a 100K three loop race with substantial elevation gain.

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

Soul Crusher is a trail race in Crystal Lake, IL offering 10 mile and 5 mile options on single track forest trails with looped sections and occasional extra mileage. Packet pickup is available the day before and a 3 hour 30 minute cutoff ap..

An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Miner 49er in Dubuque, IA features 25K and 50K runs on single-track and prairie trails with significant elevation gain, three aid stations, and views of the Julien Dubuque Monument, Horseshoe Bluff, and the Mississippi River.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

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.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A winter trail event at Governor Dodge State Park offering 50K, 25K and 15K courses on mixed horse trails and prairie paths. Aid stations, crewing and pacers are available for the 50K, and part of proceeds support the Driftless Trail projec..

A Canicross-focused trail event at Lake Geneva Ziplines and Adventures offering one 4-mile loop or two loops for 8 miles, dog-powered and dog-friendly options, awards for dog teams, on-course drinks but bring a refillable vessel.

A night trail event near Lake Mills, WI offering 16 and 31 mile out and back runs on flat crushed limestone. Conditions can vary from clear to snowy; required lights and reflective gear are enforced and aid stations operate cupless.

A winter obstacle race at Lake Geneva offering 5K, 10K, a 20K Yeti Challenge, a kids course, team packs and a virtual option. Fun heats allow skipping obstacles while the Elite division requires full obstacle completion for podiums.

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

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.