National Sweetest Day 2026

National Sweetest Day marks the conclusion of the Wisconsin Trail Assail Series in Nashotah, Wisconsin, coinciding with the National Sweetest Day holiday. This event offers trail running and walking options: 5K, 10K, and half marathon distances, along with a 1K for children under 10. The event typically hosts 100 to 500 participants, taking place within Nashotah Park. The course features wide, maintained trails covered in wood chips. Over 90% of the race unfolds within the park's wooded areas, passing Forest Lake and Grass Lake. The terrain is characterized as fast and flat, suitable for trail runners seeking less technical challenges on longer distances. Families are included, with children in the 1K receiving their own bibs, and this kids' race is complimentary for registered parents.