Winter Run Series™
Winter Run Series™ is a running race on October 25, 2026 – March 14, 2027 in Oconomowoc, WI, with entry fees from $40 to $45.
- Date
- October 25, 2026 – March 14, 2027 (4 days to go)
- Location
- Milwaukee Area, Oconomowoc, WI
- Price
- $40–$45
- Sport
- Running
From the Organizer
The 22nd running of Wisconsin’s largest running series is set to explore the inner workings of Milwaukee and its beautiful suburbs.
This series plays host to six events throughout the winter season, surrounding your favorite holidays. Bring the family to participate in the 5K or 10K. Let's Conquer the Cold!
The Pumpkin Run | Sunday, October 25 | Oconomowoc, WI
The Elf Run | Sunday, November 22| Hales Corners, WI
Run Into The New Year | Wednesday, December 31 | Wauwatosa, WI
The Big Chill | Sunday, January 17 | South Milwaukee, WI
Cupid Shuffle | Sunday, February 14 | Shorewood, WI
Luck of the Irish | Sunday, March 14 | West Allis, WI
6 EVENT SERIES REGISTRATION BUNDLE
Join us for the 2026-2027 Winter Run Series! Start the series off with the Pumpkin Run and finish with the Luck of the Irish while completing The Elf Run, Run Into The New Year, The Big Chill, and The Cupid Shuffle in between!
**Must sign up for the 6 Event Series to earn the series medallion!
Events
Race-Day Forecast
Live forecast from the U.S. National Weather Service.
Race Day 1
Sunday, 10/25
High
69°
Low
47°
Partly sunny
Race Day 2
Monday, 10/26
High
59°
Low
40°
Slight chance rain showers
Race Day 3
Tuesday, 10/27
High
56°
Low
—
Slight chance rain showers then partly sunny
About Oconomowoc, WI
Population
18,385
as of 2023
City Elevation
868 ft
Nearest Airport
MKE
General Mitchell International Airport · 32 mi
Time Zone
Central Time
From Endurance Grid
A mid-size host city. Enough lodging and amenities to keep race weekend easy, without big-city sprawl.
Race Location
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Winter Run Series™, put it on the calendar, and turn “someday” into a start date.
4
Days to train
- Race
- Winter Run Series™
- Date
- October 25, 2026 – March 14, 2027
- Location
- Milwaukee Area, Oconomowoc, WI
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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 an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
More Running races near Oconomowoc, WI
Frequently Asked Questions
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How do I register for the Winter Run Series™?
Winter Run Series™
Oct 25, 2026