The first 17th Street High Heel Race, which took place at midnight on Halloween back in 1986, was a fairly small and casual affair. However, the basic building blocks were there: drag queens, a quick sprint, and, of course, high heels. As The Washington Blade reported at the time:
“…high heels [were] clearly the fashion of the weekend, as Washington held its first-recorded “High Heel Race” outside J.R.’s, a Gay bar on 17th Street. A field of 25 heel-clad contestants entered the midnight race and at 12 o’clock, they took off running—one-and-a-half blocks down the street to another popular spot, Annie’s up the stairs to the bar for a hit of Schnapps, and back to J.R.’s for the ‘finish.’ Though a few heels and gaits were broken along the way, most of the competitors crossed the finish line, though not all of them came in running.”

In the intervening years, some things have changed while others remain the same. Last year, Dave Perruzza, the longtime organizer of the High Heel Race and the former owner of J.R.’s, passed the reigns to the District. Mayor Muriel Bowser sometimes even attends the event and poses for photos with racers and spectators. Her presence is felt regardless.

Nor is the Mayor the only political aspect of the event. Last year, for example, First Lady Melania Trump was a frequent subject (some might say target) of the fun.

Some of 2018’s revelers also poked fun at President Trump’s proposed Space Force with saucy puns.

The race takes place near Halloween of course (originally held on the day, it was later moved to the Tuesday prior), and so fantastic costumes are always in evidence. There are pop culture icons like Colonel Sanders…

…the Wicked Witch…

…and Catwoman…

However, she is not the only one sporting claws.

There are, of course, lots of elaborate headdresses.


And what High Heel Race would be complete without feathers?

Over the years, the High Heel Race has become more of a family affair, with lots of children in the mix.

And yet, in the end, it all comes back to those heels.

The 33rd annual 17th Street High Heel Race will take place on Tuesday, October 29th. For more details, see the event’s Facebook page.