First Mondays Summer Trail Series

Lace up your trail shoes for the First Mondays Summer Trail Series, a refreshing 5K trail race set for August 3, 2026, in the picturesque landscape of Iola, Wisconsin. Held at the renowned Iola Winter Sports Club, this event is the championship finale of a vibrant summer series, offering a unique opportunity to explore groomed trails that wind through diverse terrain across 160+ acres. Runners can expect a course that combines hilly and wooded sections with open stretches, designed to be both fun and introductory for all skill levels.

What truly sets this race apart is the thrilling "vertical challenge" integrated into each event night, where participants test their mettle by racing to the top of a different ski jump. This, combined with a family-friendly atmosphere that includes a free 1K kids' race, music, food, and a mountain bike skills area, makes it an ideal outing for runners and their supporters. Typical race day conditions in early August bring highs around 83°F and lows around 60°F, with a slight 13% chance of precipitation, creating a perfect setting for a summer evening run.

Beyond the 5K, runners accrue points throughout the series, culminating in a raffle ticket giveaway at this August championship event. Registration opens at 5:00 PM, with the kids' 1K starting at 5:40 PM, followed by the vertical challenge, and the main 5K race kicking off at 6:00 PM at the Iola Winter Sports Club located at E398 County Rd MM. Whether you're a seasoned trail runner or new to the dirt, the First Mondays Summer Trail Series offers an engaging challenge and a memorable community experience in the heart of Wisconsin.