Cupid Shuffle - Wauwatosa

The Cupid Shuffle is part of Wisconsin’s largest running series, the 21st Annual Winter Run Series, held in Wauwatosa, WI. Scheduled for February 15, 2026, this event offers both 5K and 10K race options, inviting participants to run or walk through the scenic heart of Milwaukee and its suburbs. The Cupid Shuffle encourages a family-friendly atmosphere, perfect for celebrating loved ones by crossing the finish line hand-in-hand.

Participants receive a gender-specific long sleeve shirt, finisher medal, post-race snacks, professional chip timing, and free digital race photos. The event is designed to keep runners active and engaged during the winter months while enjoying the city’s charm. Visit the organization's website for the most recent information.