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.
Distances & Pricing
Race Location
About This Sport
From Endurance Grid's Founder
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.
Coming Up
More running races in CT
Spring Street Mile & 5K Presented by PTSMC
5K
Acrisure Branford Road Race
Ambulance Driver 5K at BADSONS Brewery
5K
17th Annual Saybrook Point 5k Road Race 2026
5K
Frequently Asked Questions (FAQs)
- What is the Winter Wonderland 5 Miler?
- Winter Wonderland 5 Miler is a running event held in Milford, CT. Learn more about the different endurance sports here.
- When and where is the Winter Wonderland 5 Miler?
- Sunday, January 31, 2027 in Milford, CT at P.O. Box 57, Milford, CT. Check the official event page for exact start times and wave schedules.
- How do I register for the Winter Wonderland 5 Miler?
- Registration is handled through their official registration page. Confirm pricing, distances available, and sign up there.
Winter Wonderland 5 Miler
Jan 31, 2027