Trail Running calendar near Oconomowoc 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.

Join the Winnetka Turkey Trot on Thanksgiving morning for a fun 5k on the Green Bay Trail with Family Trot and Speedy Trotters divisions and a rolling start. Festive vibes, kids get #1 medal and proceeds support local charities.

Join the Brooks Midwest XC Championships on Nov 29, 2025 at UW Parkside in Kenosha, WI. Multiple races award medals and offer a shot to qualify for the Brooks XC Championships in San Diego.

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.

Challenge winter single track trails at Veteran Acres and Sterne's Woods in Crystal Lake on a triple black diamond course offering 50K, 10K and relays. The 50K is five laps of a 10K loop with a warm Gnome Depot serving hot food and coffee.

Take on the 50K MASHUP SLAM, a Midwest trail series that spans eight scenic events and rewards runners who finish five races with a special finisher buckle. Top series placers earn awards at the final G.O.A.T.z or Miner 49'er event.

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.

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..

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.

Run the NK50k in Greenbush, Wisconsin on April 11, 2026. Choose 50K or 25K point to point routes across rolling ski tracks, rocky Ice Age Trail sections and lofty ridgelines, with aid stations, shuttle service and post run food; expect to b..

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

Join the Earth Day trail run at Veterans Acres in Crystal Lake offering 50K, 15 mile and 5 mile options on a rolling 5 mile single track loop around the pond. Enjoy homemade aid station treats and a friendly, eco minded race atmosphere.

Run 10K, 25K, 50K or 50 Miler loops at Deer Grove Forest Preserve West in Palatine. Mostly wide non technical trails, a single aid station, pacers allowed for 50 Miler after four loops, and on course shenanigans promise a fun day.

Run under the stars at Moonlight Meltdown on April 25 in Belgium WI, with chip timed 5k road and a Sunset Safari 10k including a trail through Harrington Beach State Park. Shirts, post race food and a finish party at KYOTES.

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.

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 rolling hills and changing trail footing along a scenic Ice Age Trail section at Rice Lake Nature Trail in Whitewater, WI on June 20, 2026. Choose 10K, half marathon or 50K for a rewarding summer trail challenge.