Trail Running calendar near Cross Plains 2025-2026

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

The Guv'nor Frozen 50 at Governor Dodge State Park on December 6, 2025 offers 50K, 25K and 15K on scenic winter single track with plenty of climb. Enjoy well stocked aid stations and help support the Driftless Trail project.

Take on the Whitewalker Ultra 100k in Palmyra WI, a two loop 100k over scenic Ice Age Trail and Scuppernong trails. Expect rugged single track, aid stations on course, and a 24 hour finish limit for a true winter challenge.

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..

Explore scenic, varied trails at Governor Dodge State Park with the Tour de Dodge, offering 50K, 27K and 10K distances on March 7, 2026. Expect well marked courses, aid stations, and postrace photos and results from the Driftless Trail Coll..

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 11 April 2026. You can run between 5 and 10 kilometers.

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 the scenic Mines of Spain in Dubuque on May 2, 2026 with 5K 10K and half marathon options. Enjoy clear course support, a custom bib and a rotating race item, plus post race food and a series gift if you register for the full series.

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.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 10 May 2026. You can run between 5 and 10 kilometers.

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..

Kettle Moraine returns June 13 and 14 2026 in LaGrange Wisconsin, offering 100 mile, 100K and shorter trail distances with plenty of Ice Age Trail scenery. The 100 mile serves as a Western States qualifier, making this a prime summer ultra.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 14 June 2026. You can run between 5 and 10 kilometers.

Take on the Whitewater Trail Challenge, a Spartan Trail race on a rugged stretch of the Ice Age Trail out and back from Rice Lake. Choose 50K, 21K or 10K across terrain that ranges from smooth singletrack to technical rock and root.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 27 June 2026. You can run between 5 and 10 kilometers.

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.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 1 August 2026. You can run between 5 and 10 kilometers.