How to Prepare an Award-Winning Steeplechase Tailgate

These veteran tailgaters have turned the tradition into an art form.

For seven years, Jennifer Kouwenberg Bordelon has been competing for top honors at the Willowdale Steeplechase tailgating contest—and there’s a reason she’s won six times. Bordelon starts planning months in advance, shifting into high gear once the theme of the competition is announced. For last year’s “Willowdale Gone Wild,” “I went with my instincts,” she says. “I went with wildlife instead of wild people.”

Bordelon, a nurse practitioner, works in an emergency room. Her husband, Johnathan, is an avid hunter, and his collection of deer, elk and bear hides provided a base for her tablescape, along with feathers, antlers and a pheasant preserved by a taxidermist. Friends with pickup trucks helped to haul in three tables and a large antique sideboard from the Bordelon’s home in Mechanicsburg, Pa., a manse that was pressed into service as a hospital during the Civil War.

An accomplished hostess, Bordelon finds silver chafing dishes and other serving pieces at estate sales. “I left it tarnished for the tailgate, to blend with the animal skins,” she says.

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Jennifer Bordelon Willowdale Steeplechase Tailgate Winner

Willowdale tailgate winner Jennifer Bordelon and family. Photo courtesy of Willowdale Steeplechase.

Bordelon buys heavy drapes from thrift shops to use as tablecloths. HomeGoods is her go-to resource “for more blingy stuff, with crystals hanging from it.”

There’s no paper or plastic at Bordelon’s tailgate. Up to 40 guests enjoy her extensive collection of china and crystal—and each year, the group gets a little bigger. The party became so popular that the folks in the adjacent front-row tailgate joined forces with them. It’s important for the hostess to look the part, starting with a broad-brimmed hat. In keeping with the wild theme, Bordelon donned a cheetah-print scarf last year. “I love Willowdale,” she says. “It’s my best day of the year.”

Having His Cake

Will Rockafellow has been tailgating at the Radnor Hunt Races since college. He’s a member of the event’s Junior Committee, and his mother, Virginia Logan, is executive director of its beneficiary, the Brandywine Conservancy & Museum of Art.

While Radnor Hunt is an event that’s close to his heart, it also commands a warm spot in his stomach. “I’ve always loved to cook, but I’m allergic to wheat,” says Rockafellow, who has celiac disease. “If I want some cake, I bake my own.”

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Rockafellow’s gluten-free recipe for lemon cake took top honors at Radnor Hunt’s 2018 tailgate competition. It’s one of several prizes he’s won.

Will Rockafellow at Radnor Hunt Races

Radnor Hunt tailgate winner Will Rockafellow (center). Photo courtesy of Radnor Hunt.

For a lively tailgate, Rockafellow starts with Bloody Marys, followed by a signature cocktail that changes each year. He also recommends lots of tasty finger foods that can be prepared in advance. “Deviled eggs are a favorite, but it’s fun to try new things,” he says. “Be flexible, because you might have to make some last-minute decisions.”

Last year, Rockafellow planned on pouring sangria but forgot to pack the red wine. “So, we ended up with a Pimm’s cup, which was fantastic.”

Rockafellow always begins the day with china. But as the event progresses, he often opts for elegant disposables. “Toward the end of the day, we go with fancy plastic plates,” he says. “We try to get things that look as close to real china and crystal as possible.”

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Poppers and Punch

Nothing welcomes guests to a tailgate better than a great appetizer. Jennifer Hayward always arrives at the Strine’s Point-to-Point tailgate with a tray of her signature bacon-wrapped jalapeno poppers.

Light bites encourage guests to keep nibbling throughout the day, and Hayward’s poppers don’t require cutlery or plating.

For Carol Mayhart and her husband, Glen, the key to a successful tailgate is being ready for any eventuality. “Plan for the weather—sunscreen, umbrella, a hat, a jacket and hand sanitizer,” she says.

Her tip for ladies who want to stroll the course stylishly and in comfort: “Wedge shoes are the best.”

Carrie Smith Wedo's tailgate at Point-to-Point.

Carrie Smith Wedo’s tailgate at Point-to-Point.

Over the years, the Mayharts have joined forces with two friends to establish a large communal tailgate spot at Point-to-Point. “We can really spread out and have a great group of friends to enjoy the festivities with,” she says. “We also plan a game or two for the kids. The ring toss and a giant Jenga are favorites.”

Each year, Carrie Smith Wedo serves up her signature Point-to-Point Punch. It’s a colorful and refreshing rum drink—and typically the first thing guests sample when they arrive at the Wedos’ front-row tailgate spot.

The punch is a little different every year, as she mixes up the various fruits and juices she puts into it. “It’s a morning-into-afternoon drink and always a huge hit,” says Wedo. “We really don’t measure anything. It really is just tasting as you go and making it to your alcohol-content preference.”

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