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Dress to Impress at the Virginia Gold Cup

When it comes to dressing for a steeplechase race like Virginia’s Gold Cup, rule No. 1 is: the brighter, the better.

By Stephanie Kanowitz April 28, 2023 at 8:50 am

A century-old annual tradition is off to the races on May 6, when the Virginia Gold Cup returns with general admission for the first time since 2019. 

“Because of the pandemic over the last three years, we’ve been very limited,” says Al Griffin, chairman of the race, which has taken place at The Plains’ Great Meadow steeplechase course since 1985. In 2020, the race still happened, albeit sans spectators, and for the past two years, the number of racegoers has been reduced.  

The only time the race didn’t happen since the first run in 1922 was during World War II.  

Griffin expects about 40,000 people to watch the cup’s seven races on site while showing off brightly hued dresses, sports coats, and head-turning fascinators. 

“You see some very interesting outfits, especially when the hat contest rolls around,” Griffin says. “You don’t wear jeans,” he adds. “It’s a fancy event.” This year’s judges will be DC fashion influencer Barnette Holston, WUSA9 producer Blair Wheeler, and Middleburg Life and Hunt Country editor Kaitlin Hill.

A tailgate contest with renowned chefs as judges will assess the best picnic spreads by theme and presentation. “Many people bring their fine china, their candelabras,” Griffin says. No walk-up food sales are available. 

New this year is the 1922 Club, an area of Members Hill, which offers the best views of the course, with catering and an open bar.

The horses — about seven to nine will run in each race — are almost second fiddle to the feasts and festive fashions, which are a staple of steeplechases and a nod to their high-society air. 

Horses at Virginia Gold Cup
Photo by Richard Clay

Steeplechasing in Virginia dates to George Washington and Thomas Jefferson’s time; the two were known to compete in jumping fences, according to the cup’s website. Organized races began in Fauquier County in 1844, and eight sportsmen at the Fauquier Club in Warrenton put together the first Virginia Gold Cup almost 80 years later. 

In 1924, the race relocated to Broadview Farm near Warrenton and began using national steeplechasing rules. That’s also when the purse structure began, Griffin says, adding that this year’s purse (prize money that goes to the winning horses’ owners) is about $400,000. 

Additionally, spectators can bet on their favorite four-legged contestants. Great Meadow is a pari-mutuel wagering facility, meaning winning bettors get a share of the total amounts wagered. 

Today, “the races are a multifaceted thing, and by that, I mean, yes, the horse race is going on, but it’s also usually a gathering spot for old friends and multigenerational family reunions,” Griffin says. “And then, the backdrop for this all is that it’s a charitable organization.” 

In the past 10 years, the cup has given more than $3 million to charities, such as Fauquier County’s Mental Health Association, the Fauquier Free Clinic, and the Boys & Girls Clubs. 

Griffin says he hopes to see the cup continue to evolve: “Although we’ve been around for over 100 years, we’re always looking to move forward.”

Hats at the Virginia Gold Cup
Photo by Richard Clay

How to Dress for the Virginia Gold Cup 

The Virginia Gold Cup’s unofficial dress code calls for “afternoon dress”: spring dresses, low heels, and hats for women and lightweight sports coats and ties for men. But that description is a bit lacking compared to what the attendees bring to the table in reality. 

“What people are wearing to the Gold Cup is not what they’re necessarily going to be wearing in their day-to-day life,” says Naina Singla, a NoVA-based stylist. “It’s going to be a bright, bold, and statement-making look. The more fun you have with your outfit, the better. More is more for the Gold Cup.” 

Nothing is too outlandish when it comes to the hats. They don’t even have to match your outfit; “It’s more about coordination and balance,” Singla says. “Wide-brim hats look best in statement colors, whereas a fascinator can match your outfit for a more cohesive overall look.” 

Fit and comfort are also key. A millinery can help customize both the look and feel of a hat. Area shops to check out include Tops of Old Town in Alexandria and Proper Topper in DC.   “Give yourself time for finding the right hat and the right outfit,” Singla says.

Feature image by Richard Clay

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