The Wisconsin Trail Series takes place at 1327 Wall Street in Oconomowoc, Wisconsin on April 10, 2026. This event offers a half marathon distance and welcomes runners, walkers, and ruck participants. The race starts at 9:00 AM. Entry fees range from $160 to $205 depending on registration timing and options. Oconomowoc sits in southeastern Wisconsin, roughly 30 miles west of Milwaukee, making it accessible for athletes from the surrounding region. If you're planning to race here, book accommodations early since April is a popular time for spring endurance events in the Midwest.
From the Race Organizer
Welcome to the Wisconsin Trail Assail Series! 🌲🏃♂️🏃♀️ March 30, 2026 T-Shirt Update: Participants who register after March 29, 2026 will not receive a T-shirt for the first event. If you would like a shirt for future races, please select Registered After T-Shirt Deadline during registration. If you would prefer the pass without a shirt, please select All Access No Shirt. After Run from the Tax Man, we will follow up with anyone selecting the shirt option to confirm shirt size. Experience seven races over seven months—building to an epic series finale. The Wisconsin Trail Assail tours some of the most scenic routes in Waukesha County and Wisconsin State Parks, with courses for every level. Pick your challenge each month: 5K, 10K, or Half Marathon. Run it, walk it, chase a PR, or just collect trail miles with friends—the series is proudly walker-friendly. Why you’ll love it: Varied terrain and views all season long Consistent, well-marked courses and friendly vibes A series-ending championship to cap your journey Ready to hit the dirt? Join the Wisconsin Trail Assail and stack finish lines all season. WTA All Access Pass & Rucking! 🚀 Skip the Lines With The WTA All Access Pass! 🏃♂️ WTA All Access Pass? Your ticket to skipping the packet pickup line and heading straight to the start line! How It Works: ✔ Register for the series in any distance 🏅 ✔ Opt out of a shirt 👕💰- this automatically gets you the pass ✔ Receive a reusable ankle strap for timing ⏱️ ✔ No check-in required – just show up and run! 🏃♂️🚀 More running, less waiting—because race day should be about the trails, not the lines. 🌲 Important Notice: Your All Access Pass is non-transferable. Sharing your pass with another individual is not permitted. If someone else uses your pass, you will forfeit your access privileges. Thank you for respecting this policy—it helps us keep the program fair for all participants. Rucking at All Events! Rucking is a physical activity that involves walking or hiking with a weighted backpack (called a rucksack). The term comes from the military, where soldiers train and operate carrying heavy loads over long distances. In civilian fitness and recreation, rucking is gaining popularity as a versatile and low-impact workout. We now offer it at all Wisconsin Trail Assail Events! More information about rucking. Series Registration: Select your distance during registration (5K, 10K, or Half Marathon). Don’t worry—you can switch distances for free at any time! Please note: series registrations are non-deferrable. Single Race Registration: Want to participate in individual events? Click on the specific race link below to register for that event. Kiddo's 1K Registration: Our Kiddo's Races are free! If your little one wants to join the fun, please register them for the individual Kiddo's race of your choice. Get ready to explore the trails, challenge yourself, and have a blast with the Wisconsin Trail Assail Series! 🌲👟
Hotels Near This Race
Find accommodation close to the start line in Oconomowoc, WI. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Race Travel Insurance
Don't forget travel insurance for April 10.
You've trained for months and booked a trip to Oconomowoc, WI.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Wisconsin Trail Series 2026 — Oconomowoc, WI?
Wisconsin Trail Series 2026 — Oconomowoc, WI takes place on April 10, 2026. The race is held in Oconomowoc, Wisconsin.
Where is Wisconsin Trail Series 2026 — Oconomowoc, WI held?
Wisconsin Trail Series 2026 — Oconomowoc, WI is held at 1327 Wall Street in Oconomowoc, Wisconsin.
Where can I find hotels near Wisconsin Trail Series 2026 — Oconomowoc, WI?
RaceHotelFinder shows hotels sorted by distance from the race venue in Oconomowoc. Use the map or list view on this page to compare options and book race weekend accommodation.
