Cupid Shuffle
Decision scores
Six 0–100 scores telling you, at a glance, who this race is for.
Best for
About the Race
Race #5: Winter Run Series Join us for the 21st annual Winter Run Series—Wisconsin’s largest running series! This exciting event takes you through the heart of Milwaukee and its scenic suburbs, showcasing the city’s charm and beauty. Spanning six events throughout the winter season, the series is the perfect way to stay active and embrace the winter months, all while celebrating your favorite holidays. Bring the whole family and choose between the 5K or 10K distances. Let’s conquer the cold t...
Course Profile
Course profile data unavailable for this race.
Course features
Accessibility & inclusion
Vibe & community
We don't have vibe tags for this race yet — organizers can claim the listing to add them.
History & past results
Past finisher times and year-over-year participation will appear here once the organizer publishes them.
Reviews
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Common questions
How hard is the Cupid Shuffle 5K?
We don't have a verified elevation profile yet — check the organizer's course map for the climb breakdown.
What should I wear?
Dress for ~10°F warmer than the standing temperature once you start running. Throwaway long-sleeve at the start, gloves and a hat for sub-50°F mornings, singlet plus visor when it climbs above 60°F. The race-day forecast above is the source of truth closer to the date.
When does it sell out?
No published deadline. Most races raise the entry fee in tiers and can sell out without warning — sign up early if you're committed.
Similar races worth a look
- More like this in this city: All 5K races in Wauwatosa, WI
- Same distance, same month: Best 5K races in February
- Same distance, statewide: All 5K races in Wisconsin
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