2026 First Mondays Summer Trail Series
About the Event
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 $25 with pre-registration before May 15th, 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!
Ready to test your limits? The 2026 First Mondays Summer Trail Series brings a highly anticipated 5K to Iola on June 1, 2026. Expect a fantastic route right in the heart of Wisconsin.
Races Offered
Trail running
First Mondays Summer Trail Series: June
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 $25 with pre-registration before May 15th, 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!
First Mondays Summer Trail Series: July
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 $25 with pre-registration before May 15th, 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!
First Mondays Summer Trails Series: August
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 $25 with pre-registration before May 15th, 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!
About Iola
2026 First Mondays Summer Trail Series takes place in Iola, Wisconsin, United States. The local timezone is America/Chicago.
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Race information has been sourced from the event's official website and other publicly available resources. For the most up-to-date details, please refer to the official website directly. If you notice any incorrect or missing information, don't hesitate to reach out to us by email.
