The Tree Planting Teens used to be known as "Tree Planting Princesses". For the first 1953 Festival, there was a pageant, where a queen was selected to "reign" over the "Plant a tree in '53" Festival. The first reigning queen was Marlene Elam of Westfir.

It was very popular to be a Tree Planting Princess, it also provided opportunities to travel. In 1986, the Tree Planting "Court" attended an Oakridge Day Expo in Vancouver, British Columbia, Canada, as noted in this 1987 article in the Dead Mountain Echo,

The Tree Planting Festival today focuses less on pageantry and more on personal growth and community service. Teens start by writing an essay, which is shared with organizations such as the City of Oakridge, Food Box, Upper Willamette Youth, Uptown Business Revitalization Association (UBRA), and more! The Teens meet organization members, help them with projects, and learn what it's like to work and volunteer in the Oakridge-Westfir community. Organization members then cast a vote for their favorite essay and the Teen who demonstrates the greatest community service spirit.

While we do focus less on pageantry, we do still host the Tree Planting Teens Coronation intermixed with the Talent Show. The winner and the runner-up with the most votes from their community service projects receive an Education Enhancement Fund Scholarship. After the Coronations, the Teens continue to participate in the Festival on a parade float and in other events.