Trail Running calendar near Arena 2026-2027

Experience a seven month trail adventure through the scenic parks of Waukesha County. Choose from running, walking, or rucking across distances ranging from 5K to a Half Marathon.

A trail race at Donald County Park in Mount Horeb on May 2, 2026, offering 5 km, 15 km and a Kids One Mile Fun Run; chip timing, aid stations, awards, and proceeds benefit Friends of Donald Park for trail maintenance.

Trail run in Dubuque on May 2, 2026 offering 5K, 10K and half marathon distances. The event features marked trails, basic timing, a custom bib, a rotating race item, and post-race food; series entry includes a series gift.

Event Overview The Friends of Yellow River State Forest Trail Run is the seventh annual running event held in the state forest. It takes place over two days, with events on May 8 and 9, 2026. The event is organized by the Friends of Yellow..

A classic Midwest ultra on varied glacial terrain offering 50-mile, 50K and half-marathon options with scheduled training runs, a strict no-transfer policy and on-site medical support.

A Last Person Standing backyard ultra on a private farm near Arena, Wisconsin, where runners repeat a 1.0 to 1.25 mile loop every 20 minutes until one remains. The field is capped at 75 and a waitlist is used if it fills.

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

Flat out-and-back rail-trail races near Belleville, WI on May 23, 2026 offering 50 miles, 50K, and a half marathon, with aid stations, event swag, free food and drinks, and a tunnel and trestle-bridge scenery.

Test your grit at Byron Motosports Park with tactical obstacle courses ranging from 5K to 10K endurance laps. Choose from elite vest challenges, weighted rucking, or open waves designed to honor the resilience of first responders.

A trail run at Blue Mound State Park on June 6, 2026 offering 10K and 18K courses over varied single-track and ski trails; proceeds benefit the Friends of Blue Mound State Park.

An annual trail ultra held each June with 100 mile, 100k, 50k and 38 mile options; much of the course runs on the Ice Age Trail. Registration for 2026 is by Ultrasignup lottery with a waitlist and early-invite options.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

An overnight 10 hour timed trail run at the Millville Bridle Unit in Prairie du Chien, Wisconsin on June 20, 2026. Runners complete repeated 5.25 mile loops on Driftless Area trails, with a single aid station and a 75 person limit.

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.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

Experience the natural beauty of Dubuque with trail races through the Mines of Spain Recreation Area. Enjoy distances ranging from 4 miles to a half marathon followed by a post race party with brick oven pizza and local beer.

Test your endurance at Prairie du Chien's first backyard ultra featuring a 4.167 mile trail loop through La Riviere Park. Run one lap every hour until only one participant remains or enjoy a relaxed one lap fun run.

This annual community event in Sun Prairie features a 5k race and a kids' fun run, with a course on neighborhood bike paths. Proceeds go directly to support the local high school cross country team.

Experience the beauty of New Glarus Woods State Park with trail races ranging from 5k to 16k. This annual event features forested loops and prairie views while supporting park conservation efforts.

A looped trail event at Blackhawk Ski Club with 3, 6 and 12 hour solo and relay formats plus a 1.7 mile fun run. The course features singletrack, a major climb, natural spring pool, on-course aid, and designated crew tent plots.