First Mondays Summer Trail Series
Mon, Jun 1, 2026, 6:00 PM CDT
- Location
- Iola, WI
- E398 County Rd MM, 54945
- Type
- TRAIL
Sign up and verify details on the organizer’s official page.
At a glance
A unique summer trail series offering monthly 5K races, a vertical ski jump challenge, and family fun at the Iola Winter Sports Club.
- Fun
- Competitive
- Quirky
Fun
Competitive
QuirkyGreat for
- Kids & Youth
Kids & YouthDiscover the First Mondays Summer Trail Series at the Iola Winter Sports Club, a refreshing running experience held on the first Monday of June, July, and August. Each month features a new 5K trail course, designed to be fun and welcoming for all skill levels. For an extra challenge, participate in the unique vertical race up the ski jumps. The series culminates in an August championship, with points earned throughout for raffle tickets. A free 1K kids' race and activities make it a family-friendly evening.
What to expect
- Expect a new 5K trail course each month, designed for enjoyment and accessibility.
- Test your limits with an optional vertical challenge race up the ski jumps.
- Bring the whole family for a free 1K kids' race and engaging activities.
Standout details
- Monthly 5K trail series
- New course each month
- Vertical challenge up ski jumps
- Free 1K kids' race
Auto-drafted from the public listing — confirm details on the official event page before signing up.
Distances & registration
3 optionsRegistration for all distances is through the official signup link above.
- 5K
Mon, Jun 1, 6:00 PM CDT · From $11.60
Opens Apr 20, 2026, 5:38 AM CDT · Closes Jun 1, 2026, 1:30 PM CDT
- 5K
Mon, Jul 6, 6:00 PM CDT · From $11.60
Opens Apr 20, 2026, 5:38 AM CDT · Closes Jul 6, 2026, 1:30 PM CDT
- 5K
Mon, Aug 3, 6:00 PM CDT · From $11.60
Opens Apr 20, 2026, 5:38 AM CDT · Closes Aug 3, 2026, 1:30 PM CDT
Vibe Check
Steady Effort
Steady EffortTrail + rolling terrain
- Mostly trail
- Rolling area
The course
- Trail
- Rolling
- Family-oriented
From the organizer
The First Mondays 5k Trail Race Series at the Iola Winter Sports Club is a fun new running series for 2025.
The IWSC will host a trail race/run every First Monday of June/July/August with the final night the Series Championship in August. Each month there will be a new course for the racers - think fun, exciting, introductory trail races for everyone!
We will also be hosting a vertical challenge race each series night where participants will attempt to be the first to run from the bottom of our ski jumps to the top on a different hill each event! There will be a free-1k kids race and plenty for kiddos to do while the races are going on - from music, food, mountain bike skills area, etc.
Day of registration is available and will open at 5pm each night. Kids 1k race starts at 5:40pm followed by the vertical challenge. 5k race will start after the vertical challenge at 6pm.
This is an untimed event but participants earn points throughout the series to earn raffle tickets for a giveaway at the final event in August!
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