2026 First Mondays Summer Trail Series
- Date Mon 1st June 2026 - Mon 3rd August 2026
- Time 6:00PM CDT
- Location Iola, Wisconsin
- Price $11.60
- Races 3 races
- Distances 5km
Event summary
Get ready for an exhilarating summer at the 2026 First Mondays Summer Trail Series, taking place from June 1 to August 3, 2026, at the scenic Iola Winter Sports Club in Waupaca! This exciting 5k Trail Race Series is back for its second year, offering a fantastic opportunity for runners of all levels to enjoy the great outdoors. Each first Monday of June, July, and August will feature a new and thrilling course, ensuring that every race is a fresh adventure. Participants can also challenge themselves in the vertical challenge race, racing from the base of the ski jumps to the top on a different hill each event!
Families are invited to join the fun, with a free 1k kids race for children aged 10 and under, alongside plenty of activities such as music, food, and a mountain bike skills area. Registration opens at 5:30 PM on race days, with the kids' race kicking off at 6 PM, followed by the vertical challenge and the 5k race starting at 6:30 PM. While the event is untimed, participants can earn points for prizes at the final championship in August by taking part in the races. With an entry fee of just $10 and
Families are invited to join the fun, with a free 1k kids race for children aged 10 and under, alongside plenty of activities such as music, food, and a mountain bike skills area. Registration opens at 5:30 PM on race days, with the kids' race kicking off at 6 PM, followed by the vertical challenge and the 5k race starting at 6:30 PM. While the event is untimed, participants can earn points for prizes at the final championship in August by taking part in the races. With an entry fee of just $10 and
Organiser's Description
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!
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!
Races
-
First Mondays Summer Trail Series: June
Incl. $1.60 Fee & T-Shirt
Mon 1st June 2026 (6:00PM CDT)
$11.60
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
Incl. $1.60 Fee
Mon 6th July 2026 (6:00PM CDT)
$11.60
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
Incl. $1.60 Fee
Mon 3rd August 2026 (6:00PM CDT)
$11.60
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!
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E398 County Rd MM, Iola, 54945, WI, United States
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2026 First Mondays Summer Trail Series
