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 Mondays of June, July, and August at E398 County Road MM, Iola, WI. Each month features a new 5K course and the series concludes with a championship night in August. The Pineries Running Lab is the presenting sponsor and will be present to answer running related physical therapy questions.

The program on each night includes a free kids 1k for ages 10 and under, a vertical challenge where participants run from the bottom of a ski jump to the top on a different hill each event, and the main 5K trail run. Races are untimed. Day of registration is available.

Participants earn points across the series for each event they enter on a given night. Each point equals one raffle ticket; raffle winners are drawn after the races on the final night in August. The cost per night is $10 per participant.

Proceeds from the series support construction of new trails and trail maintenance at the Iola Winter Sports Club. Additional on-site activities have included music, food, and a mountain bike skills area. Visit the organization's website for the most recent information.

  • 5K
  • 1k kids race for ages 10 and under

Race information

5 km
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.

A new annual trail race at Iola Winter Sports Club on 10/17/2026 offering 25 km, 10 km and 5 km courses on singletrack and ski trails, with aid stations, post-race snacks, medals and age-group awards.

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