One of my favourite sections of the site (even if I’ve never settled on the perfect name for it!), a look at all the Miss Oregon Teen USA titleholders who’ve gone on to compete at Miss USA or in other state pageants. It’s always inspiring to see where their journeys have taken them — whether they won a crown early on, competed once or twice and then hung up the heels or kept showing up year after year, showing persistence in their quest to walk the Miss USA stage.
Only three former Miss Oregon Teen USA titleholders have competed at Miss USA, with Miss Teen USA first runner-up Shayla Montgomery (2020) becoming the first former Teen to win Oregon in almost 30 years when she in 2024. Of the three only Olga Calderon (1985) went on to place at Miss USA.
Similarly view few former Teens have even competed in the pageant. In recent years only five of their winners from 2000 – have even tried to win a Miss title. Of those who didn’t win, former Miss Teen USA Tami Farrell (2003) got the closest, and then went on to succeed Carrie Phelps as Miss California USA 2009 after Phelps resigned.
Semi-finalist
1
Olga Calderon (1985)
Non-finalist
2
Jill Chartier (1993), Shayla Montgomery (2020)
1991
1
Olga Calderon (1985)
1996
1
Jill Chartier (1993)
2024
1
Shayla Montgomery (2020)
States competed in: Delaware, California, North Carolina
