Trail Running calendar near Monona 2026-2027

A mixed relay in Brookfield with four 3K legs per team and an optional 6K two person relay. Entry is $25 or $20 for USATF members and proceeds support the Brookfield Central Cross Country team.

The Casual Hikers 10K will take place in La Grange on Saturday 1 August 2026. You can run 10 kilometers.

A multi-format event at Pike Lake State Park on August 1, 2026 offering distances from a 0.6 mile kids run to a 13.1 mile half marathon, with shaded trails and post-race watermelon.

Sequoit Sunrise 5K in Antioch Illinois is a community fundraiser race supporting the cross country program. The route starts and finishes at Antioch Community High School and runs through McMillen and Osmond Parks, with concessions and musi..

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.

A scenic 5K trail run through the restored prairies of White Oak Savanna in Dodgeville, WI, held August 8, 2026, with on-course hydration, official timing, post-run breakfast, and the option to join festival activities including live music..

Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.

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.

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.

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm offers 5K and 15K obstacle courses, an 8 hour Infinity option, and Mudder Village with food, music and finisher items.

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.

A new trail race in Verona, Wisconsin offering 5K and 10K courses through prairies, woodlands and oak savannas. Net proceeds support Prairie Moraine Friends for park restoration; parking is limited and ride sharing is encouraged.

A three day trail event at Rock Cut State Park featuring a night 10 km plus 25 km and 50 km races, with single race entries and Triple Crown series options that award commemorative spike prizes to finishers.

Last Dot Standing in Belleville WI pairs hourly 4.2 mile runs between Belleville Community Park and Dot's Tavern until one runner remains. The weekend also features 24 hour and 48 hour races with buckles for 100, 150 and 200 mile finishes.

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

A 136 mile ultramarathon on the Ice Age State Trail through Kettle Moraine State Forest with nine staffed aid stations and substantial elevation change.

A women only Last Woman Standing trail event on a roughly one to 1.25 mile loop with 250 to 300 ft of climb per lap near Arena Wisconsin. Laps repeat every 20 minutes until one runner remains.