Ozaukee County Fair Contests

Meet the 2019 Fairest of the Fair, Jessie Schoessow!

Jessie, from Mequon, is 20 years old and a sophomore at the University of Wisconsin Platteville, where she is working toward a Bachelor of Fine Arts degree in Art Education. She is also a Resident Assistant in Hugunin Hall.

Jessie has attended the Ozaukee County Fair every year since she was born. Her family has always been active in 4-H and the Farm Bureau. She is an 11-year member of the Ozaukee County 4-H Youth Organization. Beef, drawing and painting, leather craft, and photography were only some of the projects she has taken. Jessie also showed livestock at the Wisconsin State Fair since she was 12.

“Can you sing the National Anthem?” is a question Jessie is asked often during Fair time. She has sang for multiple horse shows, demo derbies, auctions, and concerts at the Fair.

Jessie truly loves being Fairest of the Fair. Because the Ozaukee County Fair and its history are very important to her, she cannot wait for the 160th Fair.

Fairest of the Fair Contest

In August of 2019, the Ozaukee County Fair will hold its annual Fairest of the Fair contest, sponsored by 65 Incorporated.

65Incorporated-Logo-BLACK-6052 copy

Fairest of the Fair applicants must:

  • Reside in Ozaukee County or be a Wisconsin resident with a strong connection to the Ozaukee County Fair.
  • Be 18 years old as of July 1, 2019.
  • Be available to represent the county at the State Fairest of the Fairs competition in January 2020.

The Ozaukee County Agricultural Society will award scholarships of $250, $150, and $100 to the top three candidates. Plus, the Fairest is eligible for a $750 award based on completion of duties and participation in the State competition.

DEADLINE FOR APPLICATIONS IS May 1, 2019.

Fairest of the Fair Scholarship

In 2011, the Ozaukee County Fair Board established an Educational Scholarship Fund for the Fairest of the Fair. Every year since, we have presented scholarships to the top three candidates in the competition.

We are continuing our efforts to encourage young people in Ozaukee County to participate in the program. Please consider donating to the Scholarship Fund or the program. We will recognize your contributions in the Fairest of the Fair event program (Saturday, August 3, 2019) and on this website. Please click on the links below for more information.

Fairest of the Fair Scholarship Fund Donors

Fairest of the Fair Program Donations

Donate to the Fairest of the Fair Program

Junior Fairest of the Fair Contest

The Junior Fairest will participate with the Fairest at selected events during the County Fair and throughout the County.

The competition is open to both boys and girls. Applicants for the Junior Fairest of the Fair must:

  • Be no younger than 11 and no older than 13 as of January 1, 2019.
  • Complete two essays in 300 words or less
  • Meet with the judges on Saturday, August 3, and participate in the competition at 4:00pm.

APPLICATIONS ARE DUE MAY 1, 2019.  A parent must attend the County events with the Junior Fairest.

Download Application

Future Fairest of the Fair Contest

Future Fairests participate in an event with the Fairest and Junior Fairest on August 3, and then are introduced on stage during the Fairest of the Fair competition.

  • Boys and girls are welcome to apply.  
  • The applicants must be 6 years old, and no older than 10, as of January 1, 2019.  
  • This event is limited to 8 contestants.  
  • APPLICATIONS ARE DUE MAY 1, 2019. A parent must attend the events with the Future Fairest.

Download Application

Demolition Derby Rules and Applications

LOCATION: OZAUKEE COUNTY FAIRGROUNDS, CEDARBURG

FRIDAY: DEMO STARTS AT 6PM (CHECK IN VEHICLE AT 2PM INFIELD)

SATURDAY:  DEMO STARTS AT 6PM (CHECK IN VEHICLE AT 2PM INFIELD)

2019 Rules and Regulations, Event Lineup and Application

For more information including pay outs, contact Jim or Sue Pipkorn at 262-305-6824.

Truck and Tractor Pulls

LOCATION: OZAUKEE COUNTY FAIRGROUNDS, CEDARBURG

Classes and Information can be found on Midwest Truck and Tractor Pull Association Facebook Page

Please contact Anna Thomas for entry information.

Anna Thomas
1-262-210-2920

Grand Motor Crash, Inc. and Midwest Truck & Tractor Pullers Association are independent contractors, and the Ozaukee County Agricultural Society d/b/a the Ozaukee County Fair is not liable for any acts or omissions by such entities nor is responsible for the performance of their events, payouts, awards or other results related to their events.

Power Wheels Demolition Derby Rules and Applications

LOCATION: OZAUKEE COUNTY FAIRGROUNDS, CEDARBURG

During INTERMISSION of the All Star Monster Truck Tours featuring  Monster Truck Rides

Compete like the big guys in this rough and tumble – but adorable – Power Wheels version of the demolition derbies! This event takes place during the intermission of the  All Star Monster Truck Tours featuring Monster Truck Rides on Sunday, August 4, 2019.  Power Wheel demos are split into two age groups – 4 to 7 year olds and 8 to 11 year olds.  In each heat, balloons are attached to the front and rear of the vehicle. The last child with at least one balloon remaining wins each heat. Pre-registration is required – click here for rules and here for registration.