The International Gold Cup, a beloved, almost 100-year, equestrian tradition, will take place Saturday, October 24, 2020. Its history stems from the King of Spain giving the big trophy for the race. Historically, it was characterized by many horses being shipped to the U.S. from the U.K., Ireland, France, Germany and Italy to run.  Now, because many of the jockeys and trainers in the region are from the U.K., France and Ireland, the jockeys wear the colors of their respective country of origin.

From its steeplechase beginnings to the humble fields of Virginia, the races have captivated viewers for decades. The race, which usually draws large crowds, is only allowing spectators to watch from the comfort of their homes due to Covid-19. Equestrian lovers can view the race live on

Jockey on a gold cup horse

The modern-day steeplechase is a long-distance horseback riding competition. Competitors race through a course set up to emulate the challenges of hunting on horseback. Originating as a race from one village’s church steeple to the next (thus the name steeplechase), the event is enormously challenging for horse and rider as they jump stone walls, fences and hedges.

From the history and competition to the people and festivities, Virginia horse racing events provide a rich cultural experience that unites the community. Competitors mount their horses, gather up their reins and spur their equine companions across the rolling hills before them. Navigating the marked course, the horses jump over multiple obstacles in hot pursuit of the promised trophy and accompanying prestige. 

What Does Race Day Typically Include?

When social distancing isn’t a cause for concern, crowd floods the property in The Plains, Virginia, hours before the first race. As they have for decades, spectators bring picnics, host tailgates or stroll through the Tavern Tents that serve beer, wine and other delightful refreshments. And, fans can be seen with their trunks open wide tailgating and sharing hors d’oeuvres with friends and family.


Dressed in their best, attendees can also enter the crowd-pleasing hat competition. Women wearing seasonal dresses don everything from elegant fuchsia fascinators to race-day themed horse hats as they sip mint juleps, while men clad in sports coats and ties show off bowlers or top hats while toasting to wagers. No matter whether they are gathered along the rails of the track or up on top of Members Hill in tents reserved for patrons, all who attend appreciate the sheer beauty and power of the horses.

Race day typically features seven different races, in addition to a plethora of newer activities and competitions. Horses are not the only animals showcasing their talents; terriers streak across a course to compete in the terrier races.

Where is the International Gold Cup Held?

The original landscape for the Gold Cup race was tucked along the hills abutting the Blue Ridge Mountains at an estate at Oakwood. The historic venue, a residence once owned by President Lincoln’s personal physician, Dr. Robert King Stone, was apt for the commencement of what would become a historic day.

When a philanthropist and news executive bought Great Meadow, a new era of racing began. The course challenged horses and riders to new degrees, demanding new levels of athleticism and endurance. The fences at Great Meadow are higher than its original home and demand both speed and fortitude while racing the four-mile course. 

Today, the International Gold Cup has become one of the most prestigious and competitive races in America.

Today, the International Gold Cup is one of the most prestigious and competitive races in America. Viewers from across the globe will tune in to watch the fierce competition play out on the demanding course from the comfort of their homes. 

Although some aspects of the steeplechase have changed over the past century, the spirit of good hearted competition and appreciation for the bond between horse and rider remain. 

With this year’s races being hosted virtually, we hope you will share your at-home tailgates and festivities with us on social media @wineandcountrylife, as we are proud to be sponsors. For more information and to watch the races virtually this year, visit For at-home tailgating essentials, stop by our Wine & Country Shop in Ivy, VA. And, we look forward to seeing you in person again next year. ~



Wine & Country celebrates elevated living in Virginia Wine Country. Wine & Country Life, a semi-annual life & style magazine, and Wine & Country Weddings, an annual art book celebrating elegant Virginia weddings, are complemented by the Wine & Country Shop in Ivy, VA—a beautiful lifestyle boutique that brings the pages of the magazines to life. The Shop features over 40 Virginia artisans with everything from tailgating essentials and Dubarry attire to locally made foods and award-winning Virginia wines and craft beverages for your next event. Wine & Country covers the grape-growing foothills of the Blue Ridge Mountains from Lynchburg to Leesburg, including points in between like Charlottesville and Middleburg. Ivy Life & Style Media also creates other projects, including, a collection of local resources including a popular calendar of events, family services guides and features on education, health and family day trips for parents and teachers in Charlottesville, as well as the a guide to resources for Charlottesville tourists and newcomers.