Drag racers don’t usually wear hot-pink feather boas, sparkling silver gowns or feather-trimmed boots — unless they’re contestants in Key West’s Great Conch Republic Drag Race, a madcap marathon that takes place each April.

In the Conch Republic, "drag racing" is not for the faint of heart -- or weak of ankle. (Photos by Rob O'Neal/Florida Keys News Bureau)

That’s because this rowdy race isn’t designed for high-octane dragsters, but for high-heeled drag stars — female impersonators strutting their stuff complete with big hair, pancake makeup, false eyelashes and elaborate gowns or mini-dresses. (According to race organizers, however, tiaras are optional.)

Each year, more than a dozen daring divas compete in the offbeat event, which is presented by Key West’s Bourbon Street Complex to benefit the Florida Keys’ nonprofit Helpline organization.

“Officials” in black-and-white dresses designed to resemble checkered flags direct the action, while contestants race down a portion of Duval Street, the island city’s aptly nicknamed “main drag.”

In past years, they’ve even had to navigate an obstacle course of tires and trundle unwieldy shopping carts past the crowd. That crowd, by the way, usually numbers several hundred people (and they can get downright fierce about championing their favorites).

Navigating the course along Duval Street can be pretty "tiring" -- particularly for racers in towering heels.

The lively lovelies, handicapped based on the height of their heels above the regulation minimum three inches, are judged on their speed. Judges are also influenced by style (such as it is) — and generally aren’t above accepting a bribe or two to benefit Helpline.

While the energetic entrants TRY to sprint down the course, footwear malfunctions can slow their pace to an uneven stagger. (Sandals and stilettos are carefully prepped for the event, but it’s a rare race that doesn’t include at least one crash.) And a broken heel, the ultimate tragedy, can end a contestant’s dreams of victory.

Past years’ “athletes” have included a Lady Godiva wannabe with towering patent-leather boots, a perfectly-coiffed Barbie Doll clone and a goddess-sized diva whose purple grass skirt didn’t quite match her magenta curls. My personal favorite was a 2009 entrant fetchingly attired in a flowing pink gown, filmy wedding veil and full beard.

Some lively lovelies wear sporting attire with their heels -- a smart choice given the course's peculiar challenges.

The drag challenge is part of Key West’s annual Conch Republic Independence Celebration that commemorates the Florida Keys’ 1982 secession from the United States — a symbolic action prompted by a U.S. Border Patrol checkpoint improperly erected at the head of the island chain.

The 10-day celebration also features a gaggle of other events showcasing the Keys’ independent and eccentric spirit.

Highlights include a sea battle with tall ships and weapons that range from water cannons to flying vegetables, the so-called world’s longest parade down Duval Street from the Atlantic Ocean to the Gulf of Mexico, and an open-air bed race billed as “the most fun you can have in bed with your clothes on.”

The 2010 Conch Republic Independence Celebration is set for April 16-25, with the drag race Saturday, April 17. If you’re in Key West at that time, “drag” yourself over to Duval Street and check out the action. Chances are you’ll have (ouch — wait for it) one “heel” of a good time.