The Windmill's Reindeer Dash 5k

DEC

19

2026

A community 5k and family fun run in Freeport with festive attire, live music, and a farmers market at the Gazebo. Proceeds support South Walton High School cross country and track and field programs.

Sat 19 Dec 2026

Freeport, Florida

Website

5 kilometers

Always double-check with the organizer's website! This page may contain affiliate links.

The Windmill’s Reindeer Dash & Ugly Sweater 5k Family Fun Run

This event is a community 5k and a separate family fun run held in Freeport, Florida. Participants are encouraged to wear festive Christmas attire, including ugly sweaters. The event includes live music and a farmers market with vendors offering gifts and treats.

All ages and pets are welcome. Packet pick up, the start line, the finish line, and the after party are located at the Gazebo at 1871 Great Bend Road, Freeport, FL 32439. Awards are presented for the top three overall male and female finishers, with awards given shortly after the race finish.

Proceeds from the event benefit South Walton High School’s cross country and track and field programs. The format combines a scored 5k distance and a noncompetitive family fun run, making both a timed race option and a recreational option available on the same day.

Distances: Visit the organization's website for the most recent information.