Trail Running calendar near Woodman 2025-2026

Test your endurance at Woodpecker Six, a six hour trail run through Pinicon Ridge Park near Central City, Iowa on November 8, 2025. Tackle a 1.2 mile loop with big climbs, enjoy aid stations and a heated lodge for midrace comfort.

Take on scenic, technical single track in Mines of Spain park near Dubuque, IA with a 25K or 50K double lap option. Stone steps, stream crossings and steep climbs make this a rugged and rewarding fall trail challenge.

Guv'nor Frozen 50 is a winter trail run at Governor Dodge State Park with 50K, 25K and 15K over mixed single and double track, dirt paths and prairie. Bring high visibility orange for hunting season and your own bottle.

Take on the Triple D Winter Race in Dubuque County on January 17, 2026 with bike and run distances for every level. Organized by local volunteers, the day ends with warm food and drinks at 7Hills Brewery Event Center and prizes for top fini..

Run or skate across frozen Lake Mendota at the Frozen Assets 5K, starting and finishing at The Edgewater hotel. Enjoy skyline and UW campus views while taking part in a chilly festival favorite, with options for walkers, runners, and skater..

Run the Sap Run Scramble at Embark Maple Farm, a 5K through maple woods with maple snack stops or a Last Person Standing lap challenge. Expect rugged, muddy trails, wood fired pizza, live music and sugarhouse tours.

Run rolling prairie, single track and sandy hills at the Donald Dash in Donald County Park near Mount Horeb, WI. Choose 5 km or 15 km and support Friends of Donald Park as proceeds fund trail upkeep.

Run scenic trails in Yellow River State Forest on May 8 and 9, 2026 with 5K, 10K and half marathon options. Family friendly Friday 5K allows leashed dogs and Dirty Double entrants get a hand crafted race mug.

Rumble on the Ridge is a Last Person Standing run where runners repeat The Drifty Mile loop of about 1 to 1.25 miles with 250 ft of climb and a 20 minute cutoff. The course changes yearly and direction flips every four hours.

Run scenic resort trails and ski hills at Chestnut Mountain Resort in Galena with sweeping views across the Mississippi into Iowa and Wisconsin. Choose 4 hour or 8 hour timed loop formats, enjoy a post race meal and lively after party.

Join the Sugar Badger 50/50 and Half in Belleville, WI for flat, scenic out and back runs on the Badger State and Sugar River State Trails with 50 mile, 50K and half marathon options. Expect trestle bridges, a quarter mile tunnel, aid stati..

Experience Dances with Dirt Devil's Lake, a midsummer trail run on scenic glacial terrain near Baraboo, Wisconsin. Choose distances from 10K to 50 miles and enjoy aid stations, a finisher medal and post race food and a cold brew.

Storm the Farm invites trail runners to tackle single track, bluff climbs and Cedar Creek crossings at Briggs Outdoors in Winona, Minnesota. Distances from 5k to a 43k ultra; pre registration required and the event is cupless.

Test your limits at Last Dot Standing and the 24 hour and 48 hour races in Belleville, WI September 18 to 20, 2026. Run the scenic out and back course, chase mileage buckles and cash prizes in this endurance festival.

Join Goose Bumps in Stoddard, WI a fundraiser by River City Running Club with timed loop 6 hour and 24 hour options for runners and walkers of any distance. Enjoy an aid station, post race meal, games and the chance to log big miles.

Test your legs on rugged, scenic loops at the Swiss Valley Trail Races with 50K, 25K and a 5.2 mile course. Enjoy creek crossings, big climbs, free camping and showers while supporting local conservation; registration opens Jan 1, 2026.

The Mines of Spain 100 offers 100 mile and 100 kilometer trail ultraruns on scenic loops around Dubuque's Mines of Spain. Expect rugged singletrack, steep climbs and Mississippi River views on a challenging multi loop course.