First Mondays Summer Trail Series

Iola, United States • 1-3 Jun-Aug 2026

First Mondays Summer Trail Series

The Iola Winter Sports Club hosts a three-night trail series on the first Monday of June, July, and August, with the final night serving as the Series Championship in August. The series returns for a second year and lists the Pineries Running Lab as presenting sponsor; a representative will be present at each race to answer running related physical therapy questions.

Each month uses a different course for the 5 km trail race. The series also includes a vertical challenge where participants run from the bottom to the top of the ski jumps on a different hill each event, and a free 1 km kids race for ages 10 and under. Additional on-site activities include music, food, and a mountain bike skills area. Day of registration is available.

The series is untimed. Participants earn one point for each event they enter on a given night (kids race, vertical challenge, and the 5 km); each point converts to one raffle ticket. Raffle tickets are drawn after the races on the final night in August.

Entry cost is $10 per night. T-shirts are available for $25 with pre-registration before May 15; otherwise limited sizes are available at events for $30 cash. All proceeds support construction and maintenance of trails at the Iola Winter Sports Club.

Distances Visit the organization's website for the most recent information.

  • 5 km trail race
  • 1 km kids race (age 10 and under)

Race information

5 km
1k Kids Race
Vertical Challenge
Visit the organization's website for the most recent information.
Trail runs nearby

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Experience a scenic point to point run from Plover to Amherst along the Tomorrow River Trail. This half marathon concludes at the Central Waters Brewing Co for a memorable finish in Wisconsin.

Trail races of 25k, 10k and 5k at Iola Winter Sports Club on October 24, 2026, run on singletrack and cross country ski trails. Course aid and post race refreshments are provided and awards recognize top finishers.

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