Trail Running Calendar Wisconsin 2026-2027

Pine Mountain 500 on Sunday August 2, 2026 is a professionally timed event on the Pine Mountain trails. Multiple looped races offer 500 to 2000 steps, plus a Pine Muddin' off road series and weekend packet pickup.

The First Mondays Summer Trail Series will take place in Iola on Monday 3 August 2026.

Mountain trail running at Mt. La Crosse on August 7, 2026, with sprint, a 2 mile 1000' vertical run, a ruck challenge, and a kids race.

Scenic trail 5K at White Oak Savanna in Dodgeville WI with on course music, official timing, post run breakfast and a discounted festival ticket option for runners.

Lyndon Ellefson 5K Trail Run is a 5 kilometer trail race set for Saturday, August 8, 2026. A race brochure and online registration are listed for the event.

A community running event in Brule, WI offering a 5 mile point to point course on gravel and ski trails and a 2 mile out and back on Afterhours Road, with registration open May through August and a $15 fee.

Thanks Sandy in Sheboygan, WI is a 9 mile trail run at Kohler-Andrae State Park featuring beach shoreline, trails, a boardwalk and post-race snacks.

A community run/walk in Brillion honoring Mike Ariens, featuring 10K, 5K and a Kids 1K on trails and downtown routes, with finish-line ice cream, commemorative bucket hats, medals, and shuttle service between venues.

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.

Trail running and mountain bike races at the Underdown Trail near Merrill, WI feature multiple distances on well marked singletrack with boardwalks, aid stations, awards, and a postrace gathering with music.

A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.

A fundraising event for Special Olympics on August 15, 2026 at Lake Antoine County Park. Multiple run, walk, and bike distances use Fumee Lake trails and paved lakeside routes; awards, door prizes, and age-group categories are offered.

Trail races at New Glarus Woods State Park on August 15, 2026 include 16K, 8K, 5K and a free 1K kids run. Proceeds benefit Friends of New Glarus Woods State Park and awards include age-group prizes plus a 16K consistency award.

A community cross country style event at Lussier Stadium in Madison featuring a 5 km run and a 1 mile walk; established as a memorial and serving as a fundraiser for LaFollette High School middle school feeder schools.

Participate in the annual Kettle Klomp featuring a 5k run and a 2 mile walk on a scenic cross country course. This community event supports the local high school cross country team and offers awards for various age groups.

Multi-hour looped trail challenges at Blackhawk Ski Club in Middleton, WI, with individual and team relay options, plus a 1.7 mile fun run that highlights the course features and terrain.

A community event at Riverwood Nature Center offering a 5K trail run and a 1 Mile nature walk with a kids scavenger hunt and a K9 unit demonstration. The 5K has a $30 entry fee and a t shirt guarantee for pre registration.

Trail race in the Chequamegon Nicolet National Forest offering 100 mile 100k and 50k options, campground camping at Spearhead, with much of the route on the Ice Age Trail.

Trail races in St. Croix Falls on August 29 2026 featuring marathon, half marathon and 10K on mixed single track and paved trails.

Timed ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.