Fairest of the Fair/Fair Ambassador Program

FREE WITH PAID ADMISSION TO THE FAIR

Presented by Citizens Bank and Waukesha County Farm Bureau

Sponsored by Waukesha Noon Kiwanis and Carroll University with special thanks to the King Family, Pick ‘N Save / Metro Market, and the Waukesha County Historical Society and Museum for their unwavering support

Tuesday, June 24 | 5 pm

Waukesha County Fair, Fairest of the Fair – 2026 Official Competition

Held at the Waukesha County Historical Society & Museum – Grand Ballroom: 101 West Main Street, Waukesha
Judges and Contestants arrive at 5 pm
Public and Families arrive at 6:30 pm

Tuesday, June 24 | Immediately following the competition

Waukesha County Fair, Fairest of the Fair – 2026 Official Crowning

Held at the Waukesha County Historical Society & Museum – Grand Ballroom: 101 W. Main Street, Waukesha

Wednesday, July 16 | 4:30 – 5:30 pm

Fairest of the Fair Royal “Tea” Event

Held at the Leinie Lodge

The Fairest of the Fair or Fair Ambassador is selected on the basis of personality, communication skills, school and community activities, professional appearance, knowledge of, and experience with the Waukesha County Fair. Requirements for the competition include being age 18 by the competition date and having knowledge/experience with the Waukesha County Fair. They will also need to attend at least three parades during the summer of their Fair and attend the annual Wisconsin Association of Fairs conventions, held annually in January.

Everyone is encouraged to apply; applicants can be male or female. If a female is selected, she will be known at the Fairest of the Fair. If a male is selected, he will be known as the Fair Ambassador. The individual chosen in 2025 will serve as the official host and spokesperson of the 2026 Waukesha County Fair, held July 15-19. The Fairest/Ambassador will have an entire year to learn more about the Fair, have increased opportunities to engage with the community, and be mentored by the current Fairest/Ambassador. The process of selecting a Fairest/Ambassador will be applied to each future year as well. This change is fostered by reviewing programs from other Fairs across the State and information provided by the State Fairest of the Fair Program to continue to improve our program, development, and offerings.

Responsibilities of the Fairest/Ambassador include welcoming the public, interviews with the media, announcing special events, judging and participating in contests, and awarding ribbons. Throughout the reigning year, the Fairest of the Fair/Fair Ambassador attends county functions, speaks at community engagements, schools, and clubs, and participates in parades as requested. During the following year’s Fair, the Fairest/Ambassador will be a part of putting together a showcase event on Opening Day (Wednesday) of the Fair. In addition, the Fairest/Ambassador represents the Waukesha County Fair at the three-day Wisconsin State Fairest of the Fairs Competition, to be held in January in Wisconsin Dells. A scholarship for continuing education will be awarded to the Fairest of the Fair/Fair Ambassador at the end of the reign.

Now Accepting Applications

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2025 Fairest of the Fair

Sydney Miller of Oconomowoc

Sydney Miller is 18 years old and is a 2023 graduate of Oconomowoc High School. She currently attends UW Madison studying Agricultural Business with a minor in Life Sciences Communications. At college, Sydney participates in clubs such as the Association of Women in Agriculture, a professional development club focused on women in the Agricultural industry and is the Secretary for Saddle and Sirloin. In high school, Sydney was involved in basketball as a 3-time scholar athlete, the National Honor Society, the Spanish National Honor Society, LINK Crew and the FFA President her Junior and Senior year. She also received an accolade in the Kiwanis Hall of Fame for Ag Business. Outside of school, Sydney works at Miller Brothers Grass Farm, her family farm where she hopes to return after graduating college. She said being born into the agricultural industry set her up to develop her love for farming and the support has only furthered her passion. Sydney became involved with the Fair at 14 years old when she began showing swine projects and participated in the County Executive and Fair Marshal Junior Livestock Auction at the Fair. She also was involved in assisting with the 1st annual Spectacular Showmen show developed by 2023 Fairest of the Fair Ellie Szczech. Even more, she has been on the officer team for the Kettle Moraine Livestock Club where she has served as Secretary, Treasurer and Vice President and has volunteered in the 4-H Kitchen at Fair.

“Being Fairest means being that role model for the kids who have just started showing, and embodying what the Fair is all about: making life-long friendships, learning life lessons and most of all having fun. I want to encourage young kids and families to participate in 4-H, raise livestock projects and get involved with the Fair because there is always something to learn at the Fair!”

1st Runner Up  Julia Missall

Miss Congeniality  Scarlet Schwartz

2024 Fairest of the Fair

Jayden Rather of Waukesha

Jayden has been exhibiting beef and swine at the Fair for over a decade and has volunteered with Little Squealers, Little Britches, Showman of Showmen and the 4-H Kitchen. Beyond the Waukesha County Fair, Jayden graduated from Mukwonago High School as Valedictorian in 2022 and was a scholar athlete all four years of high school. Currently, Jayden attends UW-Madison, where she has achieved Dean’s list for her first two semesters and has hopes to achieve a career in medicine. She is involved in the Pi Beta Phi Sorority as well as numerous medical student organizations including the American Medical Women’s Association (AMWA), American Medical Student Association (AMSA) and MedLife. Through these organizations, Jayden has deepened her connections with her college community by raising money for fundraisers, being involved in book drives and other community directed activities. Back at home with the Waukesha County Fair, Jayden hopes to emphasize the importance of local farmers, preserving farmland, raising local livestock and educate about raising local and buying local products. She is looking forward to engaging with the community in Waukesha County and building relationships with both current and future farmers.

Past Fairests