2027 First Mondays Summer Trail Series logo

2027 First Mondays Summer Trail Series

2027 First Mondays Summer Trail Series is a trail running and running race on June 7 – August 2, 2027 in Iola, WI, with an entry fee of $10.

Date
June 7 – August 2, 2027 (228 days to go)
Price
$10
Sports
Trail RunningRunning

From the Organizer

The First Mondays 5k Trail Race Series at the Iola Winter Sports Club is back for its second year and we couldn't be more excited! We are incredibly excited to announce that the Pineries Running Lab has come on board as the presenting sponsor this year and will be at each race answering any running related PT questions! Please stop by and talk to their incredible team.

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 (10 and under) 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 530pm each night. Kids 1k race starts at 6pm followed by the vertical challenge. 5k race will start after the vertical challenge at 630pm.

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! For each event you run at each series night; kids race, vertical challenge, and the 5k you will earn one point. One point equals one raffle ticket that will be drawn after the races on the last night in August to win some great prizes from local businesses.

Each night costs $10, T-shirts are available for $20 with pre-registration before May 11th, otherwise they will be available (sizes limited) at each event for $30 cash.

All proceeds from the races goes towards construction of new trails and trail maintenance at the Iola Winter Sports Club.

We are so excited to run with you this summer!

Events

First Mondays Summer Trail Series: June$10
First Mondays Summer Trail Series: July$10
First Mondays Summer Trails Series: August$10

Typical Conditions

It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.

Typical High

75°

Typical Low

53°

Chance of Rain

41%

Based on US Climate Normals data from Rosholt 9 Nne, 11 mi from the venue.

Sunrise 5:12 AMSunset 8:38 PMDaylight 15h 26m

About Iola, WI

City Elevation

960 ft

Nearest Airport

CWA

Central Wisconsin Airport · 32 mi

Major Hub

MKE

General Mitchell International Airport · 125 mi

Time Zone

Central Time

From Endurance Grid

Line up lodging and travel early to lock in your race weekend.

Race Location

Approximate location — pin shows the host city, not the exact venue.

What Are You
Waiting For?

Every finish line starts with a single decision. Claim your spot at 2027 First Mondays Summer Trail Series, put it on the calendar, and turn “someday” into a start date.

228

Days to train

Race
2027 First Mondays Summer Trail Series
Date
June 7 – August 2, 2027

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About These Sports

This race spans more than one sport — here’s a guide to each, so you can understand what’s involved and decide if it’s the right fit. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.

Trail Running

Running off-road — dirt, singletrack, and mountain paths — from 5Ks to ultras. The terrain makes for an exciting twist and adventure in your running journey.

Running

From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.

Frequently Asked Questions

What is the 2027 First Mondays Summer Trail Series?
2027 First Mondays Summer Trail Series is a trail running and running race held in Iola, Wisconsin on June 7, 2027. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more trail running races near you or explore our sports guides to learn what race day actually feels like.
When and where is the 2027 First Mondays Summer Trail Series?
Monday, June 7, 2027 in Iola, Wisconsin at E398 County Rd MM. Check the event page for exact start times and wave schedules.
How do I register for the 2027 First Mondays Summer Trail Series?
Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.

2027 First Mondays Summer Trail Series

Jun 7, 2027

Register