Held in Russell on Friday evening, the event saw competitors dressed as the opposite sex - frocks and high heels for men; boots, suits and hats for women - complete a series of challenges while racing around an obstacle course.
The drag race is the traditional opening event in the three-day Russell Birdman Festival.
Although this was the first year the field had been open to women dressed as men as well as men dressed as women, entries were down and some regular contestants were absent.
Competitors raced in pairs from the waterfront to the Duke of Marlborough Tavern, while hurdling hay bales, climbing a gate, downing a vodka jelly, shooting a basketball hoop, crawling through a tunnel and skipping rope.
The fastest individual was 12-year-old Lily "Ben" Eketone of Russell in a time of 1m 32s.
One of the more striking entrants, wearing a triple-F cup, was "Sherri" of Auckland's Buckland Beach. His entire extended family was spending the weekend in Russell to celebrate his mother's 70th birthday and had booked the holiday before discovering it was the weekend of Birdman.
"My daughters put me up to it," he said.
Winners
Fastest individual: Lily "Ben" Eketone (1m 32s);
Fastest duo: Mike "Miss Humpalot" Friedlos and Sandy "Mark the builder" Fitzgerald;
Fastest team: Anika Whapshott and Steph Godsiff as "Dos Amigos" (2m16s);
Best-dressed individual: Alex "Alexia" Claydon;
Best-dressed team: "Dos Amigos". A 12-year-old girl dressed as a schoolboy has won the 2012 Birdman Festival drag race.