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Meet the winners of the 25th Annual Great PUPkin Dog Costume Contest

And see the cutest costumes from the event!

The Great PUPkin Dog Costume Contest - Missy Elliott
Photograph: Tayler Smith | Dusty Doggerton as Missy Elliott
Photograph: Tayler Smith | Dusty Doggerton as Missy Elliott
Melissa Kravitz Hoeffner
Written by
Melissa Kravitz Hoeffner
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Creativity and canine adoration combined on Saturday, October 28, when hundreds of dog lovers and their pets gathered in Fort Greene Park for the 25th Annual Great PUPkin Dog Costume Contest.

Over 100 dogs participated in the mainstage costume contesthosted by Park Users & Pets Society (PUPS), a nonprofit dedicated to the dog owners and dogs who frequent Fort Greene Park—walking the stage to show off intricately homemade, deeply creative outfits. Tail-wagging spectators packed the monument steps and all sides of the park, crowding under the shade of golden leaves on an unseasonably 80-degree day. 

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The “Blues Clues Brothers” opened the show with a lineup of dog-themed cover songs, followed by an official welcome by New York’s Attorney General, and former city councilmember and PUPkin judge, Letitia James.

“It’s been a rough week, for all of us,” James acknowledged. “I want all of us to think about one another. We came here today because we need a little levity. We need to laugh … Welcome to the greatest show on Earth.” 

As Judge Dan Fox (dressed as Bob Barker) said, a lot of underutilized MFAs came to show off across the stage. This is Brooklyn, after all. 

A water tower at the great pupkin dog costume contest
Photograph: Tayler Smith

The crowd “oohed” and “ahhed,” cheered and laughed and screamed at costumes including a dancing David S. Pumpkins duo, the 50th Anniversary of hip-hop, a dog disguised as a panda (who took home second place), a furry doodle decorated like a Brooklyn water tower, a dog working the double shift at the Fritos Factory (if you know, you know), Missy Elliott (third-place winner), a golden “noodle”, and, of course, a few Barbies, Kens and Allen.

Hyperlocal costumes grasped the audience’s attention, including two canine Rat Czars, New York City’s weather plagues (remember June’s unsettling yellow sky), an elaborate New Year’s Eve ball drop complete with a playlist and Planet Fitness hats, a cockroach invading an apartment, and a dog King Kong atop a cardboard Empire State Building. 

Many non-competing dogs supported their furry friends in store-bought pumpkin, mermaid, hot dog and superhero costumes, and of course, Travis and Taylor, a canine couple, were spotted by the puppy paps.  

This year’s judges voted on their favorite costumes, bringing out the top three for the crowd to cheer on and determine the winner, a clear audience favorite based on the enthusiastic noise.

The Empire State Building at the great pupkin dog costume contest
Photograph: Tayler Smith

Gertrude, an 18-year-old chihuahua from Ridgewood took home the top prize, to a resounding cheer from the audience who chanted “David Byrne! David Byrne!” when Gertrude’s beloved costume wasn’t named as a judge’s choice. Her tiny head popping out of a gray suit made quite an impression, while her owner, Christina O’Toole, supported her with a lampshade on her head. 

O’Toole adopted the small pup at age 10 from an ex’s coworker, and the duo have shared many costumes over the years: Bat and vampire, Wallace and Gromit (Gertrude was obviously the human), a golden retriever and cockroach, to name a few. This was, however, the dog’s first time entering any type of competition. O’Toole walks dogs locally and learned about the event from her clients. 

After seeing Byrne’s film Stop Making Sense at BAM earlier this month, the costume felt inevitable. O’Toole purchased a toddler suit online, altered the proportions a bit, and put a lunchbox inside for Gertrude to comfortably sit in.

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For future contestants, O’Toole advises, “Go with something that you’re interested in, and know your audience.” 

When she’s not earning accolades on stage, Gertrude loves running on Rockaway Beach, and, like many Brooklynites, eating meat and cheese. 

2023 winners

First place: Gertrude as “David Byrne: Talking Heads”

Gertrude as David Byrne
Photograph: Tayler Smith

Second place: “Panda”

Panda third place winner at the great pupkin dog costume contest
Photograph: Tayler Smith

Third place: Dusty Doggerton as “Dog Can’t Stand the Rain: Missy Elliott”

Dusty Doggerton as Missy Elliott the third place winner at the great pupkin dog costume contest
Photograph: Tayler Smith
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