Trail Running calendar near Glendale 2026-2027

A long running Wisconsin trail ultramarathon that winds through forests, rocky ridges and glacial landforms. The event offers 50 miles, 50K and a half marathon and typically sells out quickly.

A low-impact, no-frills running event in Delafield, WI that highlights Lapham Peak State Park and raises funds for Tall Pines Conservancy. Races range from a Half Marathon to a free kids 1K.

A spring trail event at Pringle Nature Center featuring a 5K trail run and a 2 mile fun run or hike through hilly, dirt trails; proceeds support environmental education at the nature center.

Big Climb Wisconsin on May 16, 2026 in Madison is a team-based stadium climb that features stairs, ramps, and concourses. The event honors patients and survivors and awards participants a finisher medal while supporting efforts against bloo..

Dirt Circus Chicago on May 30, 2026 in Crystal Lake, IL gathers the local trail running community for a social run, expo, food, raffle, and vendor booths. Two route options and a city specific t shirt preorder are available.

Backyard Nonsense is a timed trail running event at Richard Bong State Recreation Area on June 6, 2026, offering 3, 6, 12 hour races and two 24 hour formats with group campgrounds reserved and a required Wisconsin State 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 event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 50K, half marathon and 10K, and the trail terrain ranges 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 prairie trail run and walk at Lapham Peak State Forest on July 11, 2026 that raises funds for prairie management, offers awards and shirts for early participants, and includes merchandise, seed sales and on-site food.

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 in Sheboygan, WI with beach, boardwalk and inland trails. Single aid station on course, cupless refreshments, podium awards for top finishers and a commemorative finisher token.

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.

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.

Trail race at Paul Douglas Forest Preserve on August 23, 2026 offering approximate 4, 9.5 and 13 mile courses. Part of the Dick Pond Athletics Darn Tough Trail Race Series with proceeds benefiting Chicago Area Mountain Bikers.