Trail Running Calendar Wisconsin 2026-2027

The 17th Annual Crossroads Trail Run offers 2K, 5K and 10K trail courses at Crossroads at Big Creek Nature Preserve in Sturgeon Bay with chip timing, awards and proceeds supporting environmental education.

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 June 13, 2026 trail running fundraiser at Mt. Ashwabay with 50K, 25K, 10K and a 5K fun run with obstacles. The looped course moves through old growth maple and hemlock with panoramic views of Lake Superior.

A trail running event on June 20, 2026, near Rice Lake in Whitewater, Wisconsin, using an out and back section of the Ice Age Trail. Routes range from 10K to 50K and include varied footing from smooth to technical.

An overnight 10 hour trail run on a 5.25 mile loop at the Millville Bridle Unit near Prairie du Chien, WI, limited to 75 runners with a single aid station and basic on-course services.

A 12th annual 1.5 mile trail run at Whitetail Ridge Ski Area in Sparta, WI on June 20, 2026. The in person event includes more than ten muddy obstacles, runs for four hours, and has tickets from free to USD 49.87.

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..

Bear Cupboard Run in Minocqua on June 27, 2026 features a half marathon, a 5K run and walk, and a 1K kids Cubbie run from Torpy Park. Most courses use the Bearskin Trail and proceeds benefit the Lakeland Pantry.

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 community July 4 event in Land O Lakes featuring a 5K on mixed surfaces and a youth fun run. Proceeds support Great Headwaters Trails and the Land O' Lakes community playground.

A 5K trail run and a 1 mile fun walk at the MECCA Trails in Mercer on July 4, 2026, supporting northern Wisconsin veterans. The 5K has age-group awards and T-shirt orders are due June 18.

A trail running event at Devil's Lake near Baraboo, WI on July 11, 2026, offering distances from 10K to 50 miles, marked courses with aid, post-race food and a finisher medal.

A prairie run and walk at Lapham Peak State Forest on July 11, 2026, using grass hiking and mountain bike trails. The event raises funds for prairie management and includes shirts for the first 100 participants and awards for winners.

MSRC XC 5k Classic is a cross country race at Verona Area High School on July 12, 2026. It includes a 5k and a 1.6 mile kids race, team scoring for teams of five runners, and awards across multiple age and team categories.

A locally run trail event in Solon Springs Wisconsin on the North Country Trail. Distances include 5K, half marathon, marathon and a 50/50 Mystery Ultra with a 50 runner limit per distance.

A community 5K and 10K on July 18, 2026 at Lion’s Park in St Croix Falls, WI, with a scenic mostly shaded course through the Wert Family Preserve. Race T shirts and medals are provided; timing clock used but not chip timed.

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..

An evening trail race at Nine Mile County Forest with 5K, 10K and 20K lap options on singletrack and ski trails. The looped course requires lights and provides on-course water and nutrition at key points.

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 trail event in La Crosse, Wisconsin featuring a timed 4.15 mile loop where each runner has up to one hour to finish. Entry options include individual, 2 to 3 person teams, 4 to 6 person teams, and a single-lap entry.