Trail Running calendar near Glendale 2026-2027

A free community trail running festival in Crystal Lake, IL that gathers race directors, run clubs, brands, and vendors for a social run, expo, food, and a raffle. Two route options are offered and the event is cupless.

Inaugural Carrera de las Rosas at the Shrine of Our Lady of Guadalupe in Des Plaines offers in person and virtual races, a kids run, and a wheelchair roll with an emphasis on inclusion and a cultural rose ritual.

A trail ultrarun at Richard Bong State Recreation Area on June 6, 2026 offering Backyard 24, 24 hour, 12 hour, 6 hour, and 3 hour options, on marked loops with on site camping and a required park pass.

An annual June endurance trail event featuring 100 mile, 100k, 50k and 38 mile options on mainly Ice Age Trail terrain. Entry for 2026 is by lottery with an ordered waitlist and early invites for rollovers and volunteers.

A Spartan Trail race on June 20, 2026 at Rice Lake Nature Trail in Whitewater, WI, using a scenic out and back section of the Ice Age Trail. The route offers three distances and varying trail surfaces from smooth to technical.

Push your limits at the Dawn to Dusk Endurance Run in Valders, Wisconsin, a timed trail event offering 6 to 24 hour formats on a scenic 4.5 mile lakeside loop. Live tracking and on site cabins make it an ideal weekend of endurance and camar..

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

A trail run and walk at Lapham Peak State Forest on July 11, 2026, raising funds for prairie management; events for adults and youth, first 100 registrants receive a T-shirt and run winners receive awards.

Cliff Runner 10K on July 19, 2026 in Sherwood, WI is a 10K trail run on mostly single track with rocks, roots, boulders and over 500 feet of elevation gain. Registration includes a T shirt and finisher medal and a share of proceeds supports..

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

A nine mile trail run at Kohler-Andrae State Park featuring beach, marsh and boardwalk sections, one midcourse aid station, post-run snacks, and awards for top finishers.

A Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.

A community cross country style event at Lussier Stadium in Madison featuring a 5 km run and a 1 mile walk; established as a memorial and serving as a fundraiser for LaFollette High School middle school feeder schools.

Loop format trail event at Busse Woods in Ned Brown Forest Preserve on August 15, 2026. Runners complete 3.1 mile loops on crushed limestone and packed gravel with a centralized aid station and distances from 5K to 50K.

A continuous 40 or 50 mile loop race at Busse Woods on a 3.1 mile (5K) trail loop with fully stocked aid each lap and a 12 hour time limit. Personal supplies, crew zones, pacers, and on site medical staff support runners.

Multi-hour looped trail challenges at Blackhawk Ski Club in Middleton, WI, with individual and team relay options, plus a 1.7 mile fun run that highlights the course features and terrain.

A trail race at Paul Douglas Forest Preserve on August 23, 2026 offering approximate 4, 9.5 and 13 mile options. Part of the Dick Pond Athletics series with proceeds supporting the Chicago Area Mountain Bikers.

Tough Mudder Chicago at Richardson Adventure Farm on August 29 2026 offers 5K and 15K obstacle runs plus an 8 hour Infinity format, a Mudder Village with food and music, and finisher medals shirts and drinks.