They're Off! To the Gold Cup Races

You don’t have to be a horse fan to enjoy steeplechase racing—it's much more.

Familiar trumpet notes electrify the air. It’s time! You and 35,000 fans stand at attention, eyes riveted on the course, waiting for the announcer to say, “And they’re off!” Soon galloping thoroughbreds ridden by colorful jockeys thunder into view. In awe you watch these elegant horses, weighing a half ton and more, sail effortlessly over six-foot fences, like the mythological Pegasus—only these horses don’t have wings, just sheer strength, beauty, and heart.

As they gallop past, you feel the earth shake beneath your feet. The power of these animals takes your breath away, but it’s the poetry of their movements that lingers as they disappear over another fence and into the hills and dales beyond.

Welcome to steeplechase racing in Great Meadows, Virginia.

Gold Cup Races—A Virginia Tradition

Every October & May at Great Meadows in Fauquier County

Twice a year in a pastoral stretch of Fauquier County, two top steeplechase races are held: Virginia Gold Cup on the first Saturday in May, and the International Gold Cup on the last Saturday in October. On an abandoned farm rescued from yet another sprawling housing development by newspaper publisher and philanthropist Arthur W. (Nick) Arundel, these exciting races draw horse enthusiasts from all over.

But you don’t have to be a horse fan to enjoy steeplechase racing—because the Gold Cup Races are so much more than that. They’re a time-honored Virginia tradition, dating to the 1920s when eight sportsmen met at the Fauquier Club in Warrenton and organized a four-mile race over the natural walls and fences of nearby hunting countryside.

The Gold Cup race course moved around a bit until landing in Great Meadows in 1985, where the natural landscape offered a perfect course for racing, as well as for viewers to watch the races and enjoy the festivities and socializing that are just as much of a draw as the races.

Take tailgating. I went to my first Gold Cup five years ago while on a press trip and saw some of the most elaborate tailgating set ups ever. I’m talking about fine white tablecloths, candleabras, top-shelf spirits, champagne, caviar, lamb chops, crab cakes, and bottles of wine from nearby Loudoun County’s prolific vineyards.

People dress up for the Gold Cup Races: dapper young men wear preppy outfits and jaunty loafers sans socks. Beautiful, thin women wear cocktail dresses and impractical high-heel shoes. Then there are the hats. Yes, ladies, here’s your chance to wear your most bodacious hat. Better yet, go buy one just for the occasion. Pick a bright color like fuchsia or cherry red or royal blue—and of course the more feathers and frills and blooms, the better.

Of course, weather being what it is, it’s best to be prepared. Peter and I joined friends this past May for the Virginia Gold Cup. Threatening skies blanketed Great Meadows, but we were bound and determined to set up our tailgate party and enjoy the day, forecast be damned. Of course, we had umbrellas and rain jackets handy and needed them during a 20-minute downpour, but afterwards, the clouds lifted and the fun continued.

Win, Place, Show—You Bet!

Maybe You'll Get Lucky and Win Exact or Trifecta

So what do you do at a Gold Cup Race? You watch the races—natch. Usually, there are 7 or 8 races, and the courses range from 1.25 to 4 miles long. If you’re feeling lucky, you can wager money on a horse. Placing bets is popular, so you’ll see folks lined up to wager their hard-earned dollars to win, place, or show.

You can also bet an Exact, where you choose the 1st and 2nd place horses, who must win in that order, or the Trifecta, where you choose the top three winners in a race. Betting adds its own special thrill, and while I’m not normally a gambler, next time I will give it a shot. After all, the minimum bet is just two bucks, and who knows? Maybe I’ll win!

There’s also the exclusive Members Hill area, where people go to see and be seen. Here you’ll find the horse owners and the upper echelons of the horsey set. Perched on a hillside, Members Hill also offers the best views of the course, as well as proximity to the Winner’s Circle, where the horses parade before the race and the winning horses and jockeys afterwards.

Besides watching the races, getting gussied up if that’s your thing, and enjoying the pleasures of tailgating—eating, drinking, and merrymaking—you walk around and look at the other people, who are doing the same thing. Some folks rent party tents and bring together 75 of their closest friends or relatives for swanky entertaining. There are also smaller tents filled with frat boys and college kids, millennials, and even a few hipsters, looking somewhat serious and out of place.

If you’re lucky, you’ll bump into someone you know, which happened to Peter and me in May. On one of our walks we ran into a couple from church who invited us to their tailgate, where scrumptious homemade crab cakes were on the menu. Later when the races ended and a drizzle began to fall, we were heading back to our car when I saw a buddy from college. “Peggy?” he said. I guess I still look sort of like I did 40 years ago.

Loudoun County Offers Wineries & More

Dine at Excellent Restaurants Like Red's Table & Harriman's

To make the Gold Cup Race even more fun, plan to attend with friends. Better yet, make it a weekend trip and check out some of the nearby restaurants, attractions, and wineries. Here are a few places we recommend:

Greenhill Winery in Middleburg

This pastoral winery has an amazing tasting room (more like a villa) and undulating views of vineyards and farmlands. Opened in 2013, Greenhill features fabulous wines, including Eternity, a Bordeaux blend with truffle, black cherry, and raisin notes, and Philosophy, Greenhill’s flagship wine, a blend of Petit Verdot, Cabernet Sauvignon, Cabernet Franc, Merlot, and Malbec. Bold and complex, it’s a little like its namesake. A Farm Store offers picnic fixings, and there are lots of chairs and tables for relaxing with a glass of wine.

Take a walk down the lane and visit Greenhill Vineyard's cute Charolais cows.

National Sporting Library and Museum

This Middleburg museum celebrates “country pursuits,” such as angling, horsemanship, shooting, steeplechase racing, foxhunting, flat racing, polo, coaching, and wildlife. Its library boasts rare books, manuals, and periodicals, some centuries old, all related to field sports. The museum features paintings, sculptures, and decorative arts, as well as changing exhibits.

Beginning Sept. 18, a new exhibit called Sidesaddle will highlight women equestrians in flowing skirts who jumped and galloped across the countryside while sitting sidesaddle.

Find out more about the new Sidesaddle exhibit at The National Sporting Museum and Library.

Shoe’s Cup and Cork

This restaurant on N. King St. in Leesburg was once a shoe repair shop. Today it’s a cozy restaurant featuring fresh salads, sandwiches, and entrées plus cheese and charcuterie boards and delicious local libations. Out back is the Secret Garden, where you can dine al fresco, play bocce ball, and enjoy live music.

If you're looking for a cool place in Leesburg to relax and unwind, stop in Shoe's Cup and Cork.

Red’s Table

In Reston you’ll find Red’s Table, an acclaimed local restaurant owned by three brothers who grew up nearby, featuring farm-fresh produce and meats and local craft brews and wines. It’s a busy spot with an open kitchen and a patio outside overlooking a lake. We met a friend for dinner there and had an amazing meal that began with calamari enhanced with cherry peppers and spicy sausage—a nice twist on an old-standby. My friend, Judy, had a steak salad with flavorful local beef, I tried the fish of the day, a plump red snapper served with greens and Israeli couscous, and Peter sampled their meaty crabcakes.

Don't miss great food, a chic vibe, and craft beer in Reston's Red's Table

Tasting Room Wine Bar

While you’re in Reston, pop over to this posh wine bar run by the family that owns Boxwood Estate Winery in Middleburg. With its urban chic vibe, The Tasting Room Wine Bar feels like the perfect place to unwind with a glass of lovely Boxwood wine and a light snack. Or stop in the winery just south of Middleburg for a tour and a tasting.

For a lush after-work glass of wine, visit the Tasting Room Wine Bar.

Or back in Middleburg explore the beautiful grounds and taste more fine wines at the Boxwood Winery.

Salamander Resort & Spa

This Middleburg resort is a lovely place to lose yourself for a while. Featuring equestrian-themed décor, plush rooms, a serene spa, trail rides, zip lines, exquisite food, and beautiful grounds, it’s the ideal place to stay during the Gold Cup Races, but beware the resort gets booked way in advance for the Gold Cup weekends.

Experience Virginia Hunt Country luxury at Salamander Resort & Spa.

International Gold Cup Race

How to Attend 2018's Events

Make plans now to attend the International Gold Cup Race Saturday, October 27, 2018. First, get tickets (this event often sells out). Next, invite some friends. Then start planning your ultimate tailgating set up. Last but not least, go shopping for some fun, frilly clothes to wear. Ladies, this means finding a brilliant hat, and if high heels aren’t your thing, boots will fit right in. See you there!

Tickets start at $25 for general admission (plus a parking fee of $50) and range up to $12,000 for a 40’ x 40’ Platinum Tent Package that can accommodate 225 guests.

For more information and to find out where to get tickets, visit

Peggy Sijswerda

Tidewater Women Magazine, Editor & Co-Publisher.

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