The Winsted Ambassador organization is a program that serves as the city's public relations representatives. Each August, during the Summer Festival, young women are chosen to represent Winsted as Ambassadors. They travel across central Minnesota, attending various events in different communities, showcasing Winsted's spirit. In addition to participating in events outside of Winsted, the Ambassadors also volunteer at local community events throughout their reign.

Open registration for the Winsted Ambassador program takes place each spring, allowing young women to apply as candidates for the summer leading up to the coronation which takes place during the Summer Festival weekend, held the second weekend in August. Applicants must be between the ages of 16 and 19 (by May 31st), have a Winsted address or phone number, or attend either Holy Trinity or Howard Lake Waverly Winsted school. During their candidacy, they participate in a scaled-down version of the activities they would engage in if crowned as a Winsted Ambassador. This process helps candidates decide if they are interested in and committed to the program for a year, if selected.  The committee strives to remove any barriers for these young women by providing the wardrobe they will wear to events if crowned, soliciting community members to pull the float if their parents are unable to, and chaperoning events if needed. The goal is to offer this opportunity to any young woman who wants to be part of the program.

For over 30 years, the Ambassador program has seen numerous young women flourish, gaining self-confidence and pride in the Winsted community. The program aims to foster community involvement, create a sense of pride and spirit, and provide tools and support for the young women to develop their capabilities in poise, public speaking, and volunteerism.