Trail Running calendar near Mount Prospect 2026-2027

A timed 6 hour and 12 hour event on a 2 mile lakefront loop in Evanston that passes Northwestern University's campus. The race includes two aid stations, public fountains, handmade finisher awards, and a non alcoholic Hop Water for finisher..

Emmy's Rustic Run is a Fort Atkinson trail run and family fun day raising funds for the A-T Children's Project, featuring a 5k, a one mile walk, kids races and virtual participation.

A 30 minute run or walk up Mt. Hoy at Blackwell Forest Preserve on September 26, 2026. Entry fees support Bridge Communities to house a family for two years while they work toward self sufficiency.

A multi duration trail event at Richard Bong State Recreation Area on Sep 26, 2026. Options include 3, 6, 12 and 24 hour formats, with both a Backyard 24 loop and a continuous 24 hour Ultra available.

Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.

Multiple trail distances run on a 4 mile loop at Tryon Farm with grassy fields, singletrack and short pavement. Proceeds benefit the Tryon Farm Institute and the event is part of the Crazy Legs Race Series.

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.

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.

A community trail event in Valparaiso with a single-loop 5K and a two-loop 30K team relay hosted by local firefighters, featuring chip timing, aid stations, and team results.

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.

The Lockport Fire Foundation presents the second annual Fire Zone 5k, a community 5k run and walk on a marked loop of the Forest Preserve trail starting at Hassert Park. Registered participants present on race day receive a t shirt and fini..

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.

A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.

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 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.

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.

October 17, 2026. A trail race in Crystal Lake, IL with 5 mile and 10 mile options on single-track trails through Veteran Acres and Sternes Woods, cup-less aid, and a 3 hour 30 minute cutoff.

National Sweetest Day at Nashotah Park on October 17, 2026 offers running, walking, and ruck events from a kids 1K to a half marathon. Entry fees vary and several events include post race treats.

A fall running event at Richardson Adventure Farm in Spring Grove, Illinois on October 18, 2026. Multiple options include a 10 kilometer course combining maze and farm sections, 5 kilometer maze and farm routes, a family one mile run, and k..