Cupid Shuffle
- Date
- February 14, 2027
- Distance
- Cupid Shuffle 5K · Cupid Shuffle 10K · The Winter Run Series™ - 6 Event Series Registration
From the Organizer
Race #5: Winter Run Series
Join us for the 22nd 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 together!
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
33°
Typical Low
14°
Chance of Rain
30%
Based on US Climate Normals data from Hales Corners/Whitnall Park/Bo, 1 mi from the venue.
Host City
About Hales Corners, WI
Population
7,627
as of 2023
Elevation
792 ft
Nearest Airport
MKE
General Mitchell International Airport · 8 mi
Time Zone
Central Time
From Endurance Grid
A small town race. Lodging near the start could be limited, so book early.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Cupid Shuffle, put it on the calendar, and turn “someday” into a start date.
Coming Up
More Running races near Hales Corners, WI
Treat Trot Milwaukee
3 miles away
Firecracker Four
Less than a mile away
Race to Cure Sarcoma Milwaukee
3 miles away
Tunnel to Towers 5K Run & Walk - Milwaukee, WI
5K
4 miles away
From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Frequently Asked Questions (FAQs)
- What is the Cupid Shuffle?
- Cupid Shuffle is a running race held in Hales Corners, Wisconsin on February 14, 2027. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the Cupid Shuffle?
- Sunday, February 14, 2027 in Hales Corners, Wisconsin at 9400 Boerner Dr, Hales Corners, WI. Check the event page for exact start times and wave schedules.
- How do I register for the Cupid Shuffle?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
Cupid Shuffle
Feb 14, 2027