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Anna May Dutton started skateboarding to channel her adolescent energy. She’s still shredding two decades later.

In 1993, when Ms. Dutton was 12 and living in a Seattle suburb, she got her first skateboard—“access into the rest of the world,” she says. “I was a really hyper kid and a risk-taker.”

When Ms. Dutton, now a 35-year-old…