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Winter Wonderland 5 Miler logo

Winter Wonderland 5 Miler

Sun, Jan 31, 2027, 9:30 AM EST

Location
Milford, CT
P.O. Box 57, 06460
Type
RUN
Official registration

Sign up and verify details on the organizer’s official page.

At a glance

Double-check key details

A long-standing winter 5-miler in Milford, CT, where every stride supports local scholarships and community youth programs.

  • Festive
  • For a Cause

The 46th annual Winter Wonderland 5 Miler invites you to Milford, CT for a refreshing start to your January. This established event offers a 5-mile course with rolling hills. Beyond the run, your participation supports a meaningful cause, as proceeds and donations directly fund scholarships for Milford High School Seniors and contribute to local charities. It also helps host the free Kid's Track Summer Series by the Milford Road Runners, a 501(c)(3) organization. Join the community for a purposeful run.

What to expect

  • Experience a 5-mile course featuring rolling hills.
  • Contribute to scholarships for local high school seniors.
  • Support community charities and a free kids' track series.

Standout details

  • 46th annual event
  • Supports local high school scholarships
  • Benefits local charities
  • Funds free kids' track series

Auto-drafted from the public listing — confirm details on the official event page before signing up.

Distances & registration

2 options

Registration for all distances is through the official signup link above.

  • 5 Miles

    Sun, Jan 31, 9:30 AM EST · From $20.00

    Opens Nov 25, 2026, 10:45 AM EST · Closes Jan 27, 2027, 2:30 PM EST

  • 2 Mile Walk

    Sun, Jan 31, 9:35 AM EST · From $20.00

    Opens Nov 25, 2026, 10:45 AM EST · Closes Jan 27, 2027, 2:30 PM EST

Vibe Check

Steady Effort

  • Rolling area

The course

  • Rolling
  • Timed race
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.

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