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 cham
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.
RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
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
