Metro Weekly

Bailey Anne is the First Trans Woman to Win Miss Maryland USA

Fresh off her pageant win, Anne goes a heeled step further by attending Capital Pride events for the first time.

Miss Maryland USA 2004 Bailey Anne Kennedy – Photo: Ward Morrison

There’s always something new at D.C.’s Capital Pride Parade. The route might get tweaked. Some contingent goes particularly over the top, or there might be a surprise protest.

This year, however, one new cut in the Capital Pride carat was Miss Maryland USA, Bailey Anne.

Not only is she just a few weeks into the title, but this year marked her very first visit to the Capital Pride celebration.

“I have not felt comfortable in my own skin,” says Anne, who joined the DC News Now contingent. “To have the support of our community, for them to make space for me, that’s something I don’t take lightly.”

Anne is referring not only to the DC News Now team – particularly news anchor Cory James – but to the LGBTQ community as whole, explaining that until recently she’s been a relatively quiet military spouse, living in Maryland.

She might stand out slightly as a first-generation American, having emigrated from Cambodia when she was a child. She’s definitely receiving added attention, however, as the first Transgender woman to have won the Miss Maryland USA title.

Over the course of the pageant’s evolution, a few changes made it possible for Anne, 31, to even enter, much less win. Today, trans women are welcome to enter the pageant, as are married women, and women of any age.

“I still feel like it hasn’t sunk it yet,” Anne told Metro Weekly of her June 1 win. “I’m still on Cloud 9. I’ve dreamed of this for so long.”

Nevertheless, Anne will have to come down from that cloud and land on a stage in Los Angeles on August 4 for the next stage of her pageantry — competing for the Miss USA crown.

Regardless of the results in L.A., Anne says she’ll be busy supporting the USO, as well as trying to inspire young people.

“I hope to represent Maryland as a community who embrace one another,” she says of her title. “Pride, for me, has to be all year round. There are children out there who may not feel safe to come out. I hope we can spread a message of kindness and compassion. I am a person of faith, and I believe God gave us hearts to feel compassion.”

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