Pictured above: Juliet Taylor and Allie

By Julie Reardon

Though it was cowboy songwriter Tom T. Hall that first sang about older whiskey, younger women and faster horses, Kentucky and Virginia surely hold the monopolies on the first Saturday in May. Kentucky’s famous horse race was first run in 1875, and is probably the nation’s best-known equestrian event. Here in suburban Northern Virginia however, the Kentucky Derby is held on Gold Cup day, where it shares top billing with the Virginia Gold Cup steeplechase race meet, held at Great Meadow in The Plains, Va.

Faster Horses

With crowds of up to 60,000 in attendance, the Gold Cup is to Washington D.C. what the Derby is to Kentucky: a premiere social and sporting events. Arrangements and tailgating parties are planned months, even years, in advance; with prime tailgating and parking spaces usually sold out long before race day. You can, however, still get general admission tickets starting at $65 up until race day by contacting www.VAGOLDCUP.com or calling 540-347-2612. The Virginia Gold Cup is where steeplechasing in Virginia reaches its zenith. Unlike the dirt oval track at Churchill Downs, the Virginia Gold Cup racetrack places unique demands on its horses and riders, given that it spans a long and varied terrain with a range of fences.

Even though this issue will have only been on the streets for a couple of days, Gold Cup 2026 takes place on the 2nd,  you may just get in under the wire for the 101st year the race has been held. Otherwise, you have a whole year to make a plan.

Here’s your guide to all things “Virginia Gold Cup”, including its history, what to expect, how to purchase tickets, the iconic hat contest, and a how-to guide for placing a wager.

History

Despite drawing annual crowds of more than 60,000 today, the Gold Cup has a humble origin story dating to 1844, when the first organized steeplechase was held in Fauquier County. But it wasn’t until 1922 that a small group of racing enthusiasts decided to establish a 4-mile race through the countryside, an event that has come to be known as the Virginia Gold Cup. A total of nine horses participated in a single race that year. Today, there are seven races.

Two years after it started, the Cup moved locations and was conducted under nationally recognized steeplechasing regulations. In those early years, it was common for horses and their riders to participate in both the Maryland Hunt Cup and the Virginia Gold Cup, which were held roughly one week apart. Despite the crossover appeal, only one horse, Billy Barton, and one rider, Albert Ober, ever clinched both titles in the same year: 100 years ago in 1926. There are also hat and tailgate contests and weiner dog races—something for everyone.

The country’s top steeplechasers aren’t the only fast horses you can see this month. Lighting fast, responsive and keen, able to turn on a dime and anticipate the action, polo horses, called ponies, are just as fun to watch. Polo season in the hunt country gets underway this month also, with the return of the twilight arena polo at Great Meadow Saturday nights and field polo at several locations also starting mid-May. Beginning May 19^th, the games—usually two matches each evening—start at 7 pm. Great Meadow is a world class international polo field and during the summer more than 20,000 fans–young professionals as well as families—gather with tailgates and picnics to watch the Twilight Arena Polo program. Running through mid-September, gates open at 6:30 pm each Saturday night and admission is $30 per carload. After the matches, stay for moonlight music and dancing. For tickets or more information, call our event line at (540) 253-5001, or visit: www.greatmeadow.org

Younger women

What young woman hasn’t begged for her very own pony at some point in her life? Little and big girls alike, whether they grew up with horses or only wish they had, will enjoy seeing the new spring foals and the blue-blooded horses of the hunt country at the Memorial Day weekend annual Hunt Country Stable Tour. For most people, this is the best way to visit some of the most magnificent privately-owned farms and estates in the heart of the hunt country around Middleburg and Upperville. Begun as a church fundraiser over 40 years ago, selected farms open their doors (well, their barn doors) to the public on Saturday and Sunday of Memorial Day weekend. Featured are breeding farms, training farms, hunt stables, even jousting and polo. You can pack a picnic to enjoy at one of the farms, or buy a ticket package that includes one to be picked up at the church in Upperville. To get a map and a ticket that will get you in all the farms ($25 per person) go west on Rt. 50 through Middleburg to Upperville. Trinity Episcopal Church is on your right. Tickets can also be purchased at the farms themselves. www.HuntCountryStableTour.org or call 540/592-3711.

Fine Wine

OK, Virginia does have distilleries but it’s better known for its fine wines, aged gracefully in some of the most beautiful areas of the state. A good place to sample the best of the state is at one of the many public events the wineries host throughout the season. Billing itself as the ultimate spring picnic, Great Meadow hosts a wine festival on the weekend of June 14th. Taste over 300 artisan wines and enjoy fancy food, fine art, and fabulous music all day both days. You’ll love the Virginia wine varietal taste-offs and the Virginia Versus the World smackdown, pitting Virginia wines against wines from California, Spain and France. There will be kite flying and draft horse carriage rides both days, twilight polo Saturday evening, and a foxhound parade and NAPPA Steeplechase races Sunday afternoon. We’ve even heard rumors of elephant polo! Come out and enjoy Great Wine, Great Art, Great Food & Great Entertainment at Great Meadow in The Plains. Tickets start at $25 online; for more information or to purchase tickets contact the Farm Wineries Council, at (540) 987-8265, Donna@farmwineriescouncil.org,
or visit www.winefestivalattheplains.com there’s plenty to delight the palate this month as well.

A family favorite in May, on Memorial Day weekend, the Delaplane Strawberry Festival is held at Sky Meadows State Park, Delaplane from 10am – 5pm. Sky Meadows is in the heart of Virginia’s beautiful hunt country, only an hour’s drive from Washington DC. A weekend of family fun, featuring local crafters, children’s games, hayrides, live entertainment, a raffle, an old-fashioned bake sale, antique cars, petting zoo, fresh strawberries, and more. Events include 5K Run/Walk, Strawberry Pie and Jam Contest, and the first-ever National Strawberry Eating Championship! Proceeds from the festival are used to fund the ministries and outreach programs of Emmanuel Episcopal Church, Delaplane. Admission $20/vehicle; more information or to purchase tickets call (540) 592-3556 or visit the www.delaplanestrawberryfestival.com.