Trail Running calendar near Williams Bay 2026-2027

Timed 12- and 6-hour races on a scenic 2 mile loop along Evanston's lakefront and the Northwestern campus. The event includes two aid stations, public water fountains, and handmade finisher awards.

An annual trail run and family day in Fort Atkinson that raises funds for research into ataxia-telangiectasia. The event includes a 5k trail run, a one mile walk, kids races, and a virtual participation option.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.

A fall trail event at Lapham Peak State Forest featuring timed 5K and 10K runs, accessible walk options, and a free 1K Smokey Bear run for children age 10 and under; participant shirts, awards, and post-event treats are included.

Trail Run at Indian Lake takes place on Oct 3, 2026 at Indian Lake County Park. The event is cup free, includes a free kids run with no registration, and features a post race party with live music and a raffle.

A community 5k and a 54 yard dash on October 4, 2026 in Glendale with an out-and-back course on the Oak Leaf Trail. Registration includes all-day entry to Milwaukee's Original Oktoberfest at Old Heidelberg Park.

A community 5k run and walk hosted by the Lockport Fire Foundation on October 4, 2026 at Hassert Park in Lockport, IL. Entry includes a t-shirt and finisher medal for registered participants present on race day.

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.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

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.

Trail run at Saw Wee Kee Park on October 17, 2026, over soft, twisting trails with variable footing. Bib-timed waves, part of a four-race series with collectible medal pieces and seasonal swag.

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.

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

A trail event at Deer Grove Forest Preserve offering 50K, 25K and a 5 mile option on mostly single track loops, with stocked aid stations, marked maps and an emphasis on whimsy and inclusion.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

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.