Washington DC

‘Redemption story': Meet DC's High Heel Race winner and see the dazzling looks

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The High Heel Race – perhaps D.C.’s most fabulous Halloween season tradition – returned for its 37th year on Tuesday night with dazzling outfits and sky-high shoes.

Dozens of kings, queens and anyone between turned out in their best drag for a fun run down 17th Street, but one cowpoke called Kenny Monroe galloped ahead of the rest.

“It feels amazing – I fell last year, so it’s good to be back!” Monroe said. “Redemption story.”

Photos: See dazzling looks from DC's High Heel Race 2024

Hundreds, including D.C. Mayor Muriel Bowser, turned out along 17th Street to see the race.

“This is a pretty D.C. night,” Bowser said.

The race, which began in the 1980s, is also a commemoration of LGBTQ+ history in D.C.

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It started with a group of drag queens running from JR's Bar to Annie's Paramount Steakhouse (another gay history site), where they'd take a shot on the second floor. Then, they'd run back down 16 stairs, through the crowded restaurant and back to JR's. The winner would get $100 off their bar tab (about $290 in 2024 dollars!).

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