Photography by Shawn LaChapelle

When you go to the track these days, you’re bound to see hats of all types: feathery fascinators, floppy sunhats, and hybrid hatinators, plus boaters, fedoras, and Panama hats. But back in the 1990s, 2000s, and 2010s, on one day a year, Saratoga Race Course became a sea of even more elaborate head toppers. And at the center of it all was Kathleen Christopher.

Kathleen wasn’t an organizer of NYRA’s annual hat contest, nor was she someone who owned a lot of fancy hats. Instead, she was a doll collector, who’d just gotten her hands on an Angel Cordero, Jr. doll when NYRA announced the very first hat contest in 1991. Her son had a plastic horse—Silver from The Lone Ranger—which she outfitted with a blue mask made from an umbrella sleeve and stirrups made from soda tabs. Then she enlarged a Saratoga Race Course program that showed the Saratoga grandstand, picked up a bunch of losing betting tickets from the ground at the track, and stuck it all on a hat. Cordero himself was one of the judges.

“I thought it was great,” Kathleen says. “You’ve got a jockey, a racehorse, the grandstand…you can’t lose. And someone came in with a three-tiered sombrero, and I lost. But it just put the bug in me that I’m going to keep going.”

From there, the hat contest became more popular, and Kathleen’s hats became more elaborate, sometimes taking many months to complete. She made a winner’s circle out of plastic mesh, scoured the Brimfield Antique Show for a miniature lawn jockey, and spent two weeks slowly bending plastic fencing from A.C. Moore so that it would look like a curved wrought-iron fence. She painstakingly embroidered hat bands, glued down dried herbs to replicate the dirt racing surface, and got a Saratoga baseball cap signed by countless celebrities, from George and Libby Pataki to Marylou Whitney, cutting out photos of each person and placing them next to their signature on her “Hats Off to Saratoga” hat. One of her hats features a horse stable made of felt; another, a needlepoint version of a horse cartoon that appeared in the Saratoga Pink Sheet. 

“My mother was a creative genius,” Kathleen says. “She could make anything. She always said, ‘If you’re going to do something, do it to the best of your ability.’ I would say to her, ‘Mom, I don’t even wear hats—I hate hats—but you’ve made me want to do my very best and win this contest.” 

It was Kathleen’s mother who first introduced her to the track when she was 16. “My father was furious at her for bringing me to that environment,” she remembers. “But I had the best day of my life. There were nine races, and at the end of the day, seven of my horses came in first. I walked out of there with $90. And back in the ’60s, $90 was a lot of money.” Kathleen used her winnings to buy a pink-and-white Schwinn bike from Jerry’s Bike Shop in Albany.

As the years went on, Kathleen’s hat contest entries came to have themes, like “Saratoga Has It All,” a four-tiered tribute to the track, SPAC, polo, and Saratoga’s social scene, and “Horses of Saratoga,” which featured the six types of Spa City horses: Thoroughbreds, harness horses, polo horses, equestrian horses, the horses on the Congress Park carousel, and the decorated fiberglass horse statues found around town. (She even recreated “My Petite Fleur,” the flowered fiberglass horse that in 2002 was stolen from outside of Saratoga Arms and found more than a week later in the Schoharie Creek.)

But the title of “Uniquely Saratoga”—one of three categories hat contest hats were judged in—remained elusive. In 2002, Kathleen lost to a Massachusetts man who created the entire Saratoga grandstand out of graham crackers and candy, and wore it on his head. (After he won, he broke off a piece and gave it to Marylou, one of the judges, who said, “It’s delicious!”) Another year, she lost to a guy who made a horse head–shaped hat out of a Bud Light box.

“Even though I lost the contest, people came up to me and said they only come to the track to see my hats,” Kathleen says. “I said to my husband, I have to—my fans are out there looking for me to come. But it was like torture for him when he’d see me start to make a hat. Every year he’d go, ‘You’re not going to do that again, are you?’”

Henry Christopher, a Vietnam veteran and police officer known for his serious demeanor, maintained a mild disdain for his wife’s hobby until 2004, when she spent months making a hat called “Saratoga Dreamin’.” She’d gotten a summer job at the track, and as a NYRA employee, couldn’t enter the contest herself. She spent all day trying to find someone to wear it in her place, to no avail. “Give me the damn hat,” her husband finally said, placing the sheet cake–sized accessory on his head and tying the red ribbon under his chin.

“When they announced the winner of Uniquely Saratoga was Henry Christopher, I almost fell off my stool,” Kathleen says. “He came out with a smirk on his face, and said ‘Did you hear?’” Kathleen let her husband keep the $500 betting voucher that came with the first-place finish. She just wanted the bragging rights.

It wasn’t until 2008, 17 years after her first hat contest entry, that Kathleen herself finally took home the Uniquely Saratoga title.

“It’s a tribute to my mother,” Christopher said of the winning hat, as reported in a Times Unionarticle. “She introduced me to the track 45 years ago when I was 16. She’s in a nursing home and she isn’t going to make it much longer. I’ve entered the contest every year. I’m retiring after this year.”

Kathleen intended to retire, but she did make two more hats: one called “Winner’s Circle” in honor of the track’s 150th anniversary in 2013 (she won the Uniquely Saratoga category once again), and one that was a replica of Centennial Park, which in 2015 was built at the base of Union Avenue with funding provided by Marylou Whitney and John Hendrickson. (It has since been renamed Marylou Whitney Park.) The hat had a sidewalk, benches, the fountain, the Native Dancer statue, and greenery in the background. When she showed the hat to the park’s architect, he asked if she copied his blueprints. 

“I laughed at him and I said, ‘You know, I cannot explain how these hats come out,’” Kathleen says. “I see them in my head, and they just come out my fingers; there’s no blueprints. They just appear somehow.”

NYRA’s hat contest was discontinued after the COVID pandemic, and Henry Christopher passed away in 2021 at the age of 79. Now 79 herself, Kathleen keeps her hats in garbage bags in her basement, and the fond memories of her two decades of hat contests in her heart. “I say to our son, ‘There’s not going to be a whole money left to you,’” she says. “‘But you will have a basement full of hats.’”