First Mondays Summer Trail Series

JUN-AUG

1-3

2026

A three night trail series at Iola Winter Sports Club with changing 5K courses, a kids 1k and a vertical challenge on ski jump hills. Races are untimed and each night has a per event fee of $10.

1-3 Jun-Aug 2026

Iola, Wisconsin

Website

5 kilometers

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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.