Wisconsin Trail Assail Sweetest Day Nashotah, WI   Oct 17, 2026

Celebrate National Sweetest Day by doing something truly sweet for yourself and those you care about—join a fun run or walk! Whether you’re running solo, with friends, or sharing this special day with a loved one, this event is all about spreading joy, kindness, and a little bit of sweat.

National Sweetest Day is about showing kindness and love, and there’s no sweeter way to do that than by spending time together outdoors. So grab your running shoes, spread some cheer, and make this Sweetest Day one to remember! ❤️

The trails are well-groomed and primarily wood-chipped, ensuring a comfortable running or walking experience. A small portion of the course is grass, but it is well-maintained and easy to navigate. Additionally, over 60% of the course is shaded by trees, offering a pleasant and scenic environment throughout your journey.