Winter Wonderland 5 Miler
- Date
- January 31, 2027
- Location
- P.O. Box 57, Milford, CT
- Distance
- 5 Mile Race · 2 Mile Walk
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
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.
Coming Up
More Running races near Milford, CT
4th Annual 'Net Gains 2026' Pickleball Tournament Sponsored by The Peter & Thomas DiPietro Foundation and Chris Wright - Kingsview Partners
Less than a mile away
Milford Rotary Run in the Park 5K
5K
Less than a mile away
Centurion Trail 33 Hour Ultra
4 miles away
11th Annual Milford Moves for Veterans 5K
5K
Less than a mile 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 Winter Wonderland 5 Miler?
- Winter Wonderland 5 Miler is a running race held in Milford, Connecticut on January 31, 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 Winter Wonderland 5 Miler?
- Sunday, January 31, 2027 in Milford, Connecticut at P.O. Box 57, Milford, CT. Check the event page for exact start times and wave schedules.
- How do I register for the Winter Wonderland 5 Miler?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
Winter Wonderland 5 Miler
Jan 31, 2027