2025 pioneer way Pageant ~ June 28

The Pioneer Way Pageant is a one-day, all-natural (no makeup) event for girls and boys ages 0-14. It is sponsored by Whidbey Royalty, a 501(c)(3) nonprofit organization. It’s organized and run by the reigning Miss and Mr. Oak Harbor Royalty.

Contestants must be age 0-14 on pageant day. They must have spent time on Pioneer Way within the last year, and they should be available for the 4th of July parade should they be crowned Queen/King or Princess/Prince (ages 4 and under must be accompanied by an escort).

There are seven age divisions, each with their own age-group pageant within the overall event: 

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

Yes, contestants must pre-register to participate. Registration forms can be found on the PIONEER WAY PAGEANT tab at WhidbeyRoyalty.org. There is a $35 registration fee.

Contestants should arrive no later than the check-in time designated for their age group.

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.

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.

Contestants perform the dance, walk the stage and 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 are crowned Queen/King and Princess/Prince.

Contestants are asked to wear something in patriotic colors.

Each contestant will receive a Pioneer Way Pageant swag bag.

The top two in each division will be named Queen/King and Princess/Prince and will receive a crown and sash.

Immediately following each pageant, contestants will be photographed as a group, and individual pictures will be taken of the Queen/King and Princess/Prince. A press release will be sent to the Whidbey News Times and Whidbey Weekly, detailing the events of the day and recognizing participants and winners. All Queens/Kings and Princesses/Princes are invited to ride or walk in the 4th of July parade with Whidbey Royalty (detailed instructions will be emailed following the pageant; ages 4 and under require an escort for the whole parade). Pioneer Way Pageant Royalty may also be contacted during their reign with additional opportunities for public appearances, such as during National Night Out, the Mr. Oak Harbor Scholarship Competition, and the Miss Oak Harbor Scholarship Pageant.

The Pioneer Way Pageant is a fundraiser hosted by the Miss Oak Harbor 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 2024 Mr. Oak Harbor service project is Big Brothers Big Sisters of Island County. The 2025 Miss Oak Harbor service project is The Center.

For additional questions, visit WhidbeyRoyalty.org, email WhidbeyRoyalty@gmail.com, or call 360-929-2097.

 2025 Miss Oak Harbor Court                                    2024 Mr. Oak Harbor Court

 Miss Oak Harbor 2025:  Abby Brinker                     Mr. Oak Harbor 2024:  Logan Hendricks

 1st Princess:  Dana Rivo                                            1st Prince:  Max Gammache

 2nd Princess:  Allena Locklear                                2nd Prince:  Aiden Mosquera

 Teen Miss Oak Harbor 2025:  Elena Holton           Teen Mr. Oak Harbor 2024:  Kepano Nero

 Teen 1st Princess:  Adelle Keyes                             Teen 1st Prince:  Brian Goodman

 Teen 2nd Princess:  Victoria Reyna                         Teen 2nd Prince:  Tyler Pookphant

President | Pageant Director | Royalty Director:                    River Powers

Vice President | Treasurer:                                                        Kate Hauter

Secretary:                                                                                     Lindsey Smith

Event Coordinator:                                                                      Angela Prosser

Fashion Show Director:                                                              Ashley Gisvold

Contestant Mentor:                                                                    Connie Mollerstuen

Volunteer Support:                                                                     Mara Powers, Diana Bedford

Yes, Whidbey Royalty is a 501(c)(3) nonprofit organization – FEIN 85-1091323. Your donations are tax-deductible. 

For lots of information about Whidbey Royalty, the Miss Oak Harbor Scholarship Pageant, the Pioneer Way Pageant, and the Mr. Oak Harbor Scholarship Competition, visit WhidbeyRoyalty.org. You can also find us on Facebook @missoakharbor and on Instagram @whidbeyroyalty.