Trail Running Calendar Wisconsin 2026-2027

A community trail run and walk on June 13, 2026 at Crossroads at Big Creek Nature Preserve offering 2K, 5K and 10K options with chip timing, aid stations, participant trees, and locally sourced prizes.

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 fundraising trail event at Mt. Ashwabay featuring 50K, 25K, 10K and a 5K fun run with obstacles, scenic singletrack through old growth forest, panoramic Lake Superior views, and rustic on-site camping.

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.

The Strawberry Solstice Run is a 10 hour overnight timed trail event on a 5.25 mile loop at Millville Bridle Unit in Prairie du Chien, Wisconsin. The field is limited to 75 runners and the course uses one aid station on site.

A family-friendly, mud-filled 1.5-mile trail run at Whitetail Ridge with 10+ obstacles, commemorative swag for registrants, food and kids' activities, cold outdoor showers, and free parking.

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 with a multi-surface 5K and a youth 1K fun run; proceeds support Great Headwaters Trails and the local playground.

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 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.

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 offering a 5K, half marathon, marathon, and a 50/50 mystery ultra on the North Country Trail, each limited to 50 entrants.

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..

Experience the sunset at Nine Mile Recreation Area with a series of trail runs on single track mountain bike paths. Choose from multiple distances and navigate technical terrain using your own lights as the sun goes down.

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.

Stair and trail races on Giant Pine Mountain in Iron Mountain, Michigan. Multiple distances are offered, with Deuce as two repeats and Extreme as four repeats; new trail-run options debut in 2026. Chip timed with overall and event times.

Thanks Sandy is a *9 mile* trail run at Kohler-Andrae State Park near Sheboygan, WI, featuring beach, marsh and cordwalk sections, a three hour cutoff, one on-course aid station and post-run snacks with dietary options.