Winter Wonderland 5 Miler
Winter Wonderland 5 Miler is a running race on January 31, 2027 in Milford, CT, with an entry fee of $20.
- Date
- January 31, 2027 (192 days to go)
- Location
- Milford, CT
- Price
- $20
- Sport
- Running
From the Organizer
We are excited to announce the 46th annual Winter Wonderland 5 Miler Sunday, January 31, 2027 at 9:30 am!!!!
Details to come in Fall 2026!
The proceeds and donations of this event fund scholarships given to Milford High School Seniors, donations to local charities, and allow us to host the Kid's Track Summer Series! This is a free weekly track meet for kids hosted by the Milford Road Runners. The Milford Road Runners is a 501(c)(3) organization.
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
38°
Typical Low
24°
Chance of Rain
35%
Based on US Climate Normals data from Bridgeport Sikorsky Mem Ap, 5 mi from the venue.
Host City
About Milford, CT
Population
50,749
as of 2023
City Elevation
86 ft
Nearest Airport
HVN
Tweed New Haven Airport · 10 mi
Major Hub
LGA
LaGuardia Airport · 52 mi
Time Zone
Eastern Time
From Endurance Grid
A mid-size host city. Enough lodging and amenities to keep race weekend easy, without big-city sprawl.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Winter Wonderland 5 Miler, put it on the calendar, and turn “someday” into a start date.
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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 an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
More Running races near Milford, CT
Woodmont 5K
5K · From $30 · Trubee Doolittle Park, Beach Avenue
Less than a mile away
Boys & Girls Club of Milford Ice Cream Run (5K)
5K · From $35 · Walnut Beach
Less than a mile away
Running for Water for Africa 5K
1 Mile · 5K · From $30 · Walnut Beach Pavilion
Less than a mile away
Forbidden Forest 30 Hour Ultra
700 Peters Lane
3 miles away
Plan your trip
Make it a Racecation
Coming from out of town? There's more to Milford than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to MilfordFrequently Asked Questions (FAQs)
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Winter Wonderland 5 Miler
Jan 31, 2027