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The Pioneer Way Pageant is a one-day, all-natural (no makeup), patriotic-themed event for girls and boys ages 0-14. It is sponsored by Whidbey Royalty and Oak Harbor Main Street. The reigning Whidbey Royalty Court organizes and runs the event as a fundraiser for their service project. 

Contestants perform a dance, walk the stage, present to the audience, and introduce themselves. Emcees ask each contestant an impromptu question. They are scored by a panel of judges, then the top two in each division are crowned Queen/King and Princess/Prince and are invited to participate in the Oak Harbor 4th of July parade with Whidbey Royalty.

We ask contestants to wear something in patriotic colors.

Age-group Queens/Kings and Princesses/Princes are invited to participate with Whidbey Royalty in the 4th of July parade.

The reigning Whidbey Royalty Court organizes and runs the event as a fundraiser for their service projects. They teach a short dance routine while coaching the contestants in walks, self-introductions, and overall stage presence.

Contestants must be age 0-14 on pageant day and must have spent time on Pioneer Way within the last year. Pre-registration and a $35 registration fee are required.

Contestants should arrive no later than the check-in time designated for their age group. There are age-group pageants all day long… come early to watch the pageants before your favorite contestant’s, and stay afterwards to watch the ones following. If parents or guardians can’t stay the whole day, we ask that they remain on the premises while their contestant is in our care.

Beginning promptly at the check-in time for each division, contestants will learn a short dance to You’re a Grand Old Flag and will receive coaching in how to walk and present on stage and how to introduce themselves at the microphone.

Baby Miss/Mr.  Pioneer Way, ages 0-2        Check-in: 9:30am      Pageant: 10:00-10:30am

Tiny Miss/Mr.  Pioneer Way, ages 3-4          Check-in: 10:00am    Pageant: 10:45-11:15am

Mini Miss/Mr.  Pioneer Way, ages 5-6          Check-in: 10:45am    Pageant: 11:30-12:15pm

Little Miss/Mr.  Pioneer Way, ages 7-8         Check-in: 12:15pm    Pageant: 1:00-1:45pm

Young Miss/Mr.  Pioneer Way, ages 9-10    Check-in: 1:15pm       Pageant: 2:00-2:45pm

Junior Miss/Mr.  Pioneer Way, ages 11-12    Check-in: 2:15pm       Pageant: 3:00-3:45pm

Miss/Mr.  Pioneer Way, ages 13-14               Check-in: 3:15pm       Pageant: 4:00-4:45pm

The Pioneer Way Pageant is a fundraiser hosted by the Miss and Mr. Oak Harbor Royalty. All net proceeds from the pageant, along with any donations received, will be donated to the Miss and Mr. Oak Harbor Royalty’s service projects.

Each Royal Court chooses an organization to adopt as their service project. The 2025 Mr. Oak Harbor service project is Oak Harbor Creative Arts Foundation. The 2026 Miss Oak Harbor service project is HOPE Equestrian.

 2026 Miss Oak Harbor Court                               2025 Mr. Oak Harbor Court

 Miss Oak Harbor 2026:  Allena Locklear           Teen Mr. Oak Harbor 2025: Kenneth Hendricks

 1st Princess:  Reese Wasinger                             Teen  1st Prince:  Rowan McDonald

 2nd Princess:  McKenzie Burdick                        Teen 2nd Prince:  Cesar Vigil

 Teen Miss Oak Harbor 2026:  Charlianne Eller Teen Court:  Robert Brophy

 Teen 1st Princess:  Victoria Reyna                       Teen Court:  Max Delacruz

 Teen 2nd Princess:  Isabelle Locklear