The Upperville Colt & Horse Show (UCHS) in Upperville, Virginia is the oldest horse show in the United States. It is also one of the largest and most charming equestrian events drawing top riders from around the world. The historic grounds near Middleburg are famous for the immaculate grass fields and ancient oak trees. The oaks grow throughout the grounds, even the competition arenas, defying time and industry. The beautiful trees add shade and beauty to this prestigious show. The Upperville Horse Show is a United States Equestrian Federation Designated World Championship Hunter Rider Show. Riders range from amateur to Olympic-level winners who come to compete and to socialize. The show draws an audience of 20,000 guests who come to see world-class riding. Spectators also enjoy the week of competition and activities that range from tailgating to equestrian art exhibits and a fabulous hat contest. The show ends with the popular main Grand Prix event, the $216,000 FEI 4* Upperville Jumper Classic presented by MARS Equestrian.

The Day Begins at the Upperville Colt & Horse Show

As the sun rises, riders and trainers are arriving. The tension and focus for horses and riders is palatable as they prepare for the day’s competition. Trainers lead horses stabled nearby from their trailers, and those staying onsite in purpose-built stall structures are checked and walked. It is time to stretch and get ready for a day of competition. Competitors clean and shine their tack and clothing. Barn dogs, possibly even more numerous than the horses, trot alongside their owners and investigate the stalls and grounds. All the rings are given a final inspection – hunter, jumper, schooling, and lunging. Upperville Horse Show attendees enjoy strolling the stables to see where participating barns and owners compete for the Best Tack Room Award. They set up decorations, seating areas and even full-fledged tailgates at the front of their assigned stable areas.

Under the Oaks: History of the Upperville Horse Show

In 1853, Colonel Richard Henry Dulany created the Upperville Colt & Horse Show to encourage better care and breeding of horses. Dulany’s property, Grafton Farm was the site for the show. Grafton was famous for its magnificent oak trees even then. The first-ever trophy was designed, crafted and donated by Louis Tiffany of the famous Tiffany & Co. The show has grown in prestige and renown since. Today riders of all ages – from toddlers to Olympians – take to the rings to compete while the eager crowds enjoy the spectacle and the sport. 

In 2022, Grafton Farm–the site of the Upperville Colt & Horse Show–was added to the National Register of Historic Places. Sited in Fauquier County, the region is known for its picturesque rolling hills, horse farms, wineries, and history. Among the Grafton Farm’s famous oak trees are several that date back to the Revolutionary War. There are original structures still standing. Notably, the 1895 Grandstand has been carefully restored to preserve its historic significance. In open-entry seating on the Hunter side of the property, spectators can sit under a sloped roof of charming green shingles to watch the show.

The Hunter Rider show has established itself as a major qualifier for equestrian success, both for the horses and their riders. Olympic-caliber riders regularly choose to wait and attend the Upperville Colt & Horse Show before heading to Europe with the rest of the competitive equestrian world. Each year riders worldwide look forward to competing “Under The Oaks” at the Upperville show to participate in this cherished American experience.

Today more than 2,000 horse and rider combinations show up for the week of competitions. This makes it one of the larger horse shows in the United States, as well as the documented oldest. The National Show Hunter Hall of Fame and the Virginia Horse Show Association named Upperville the Horse Show of the Year. UCHS is a 501(c)3 charitable organization. Funds raised support The Churches of Upperville Outreach Program and other area charities.

Food & Shopping at the Upperville Horse Show

Vendors set up shop throughout the grounds of the Upperville Colt & Horse Show. Local boutiques display their wares alongside international equestrian brands like Dubarry of Ireland, as do artists and antique vendors like Baileywyck Antiques. If you’re missing a grand hat to mark the occasion, you won’t have to walk far to find some gorgeous choices. Food vendors are also scattered throughout to offer refreshments. And, of course, the popular old-fashioned lemonade stand never fails to deliver smiles.

The Horses & Horsepower Classic Car Show & More

The day before the official start of the show, UCHS holds a “Jump4Fun Day”. This is an informal day where any rider can sign up to test the courses and jump their mounts. Over the course of the week, other competitions round out the experience alongside the horses. The traditional Jack Russel Terrier races and the Horses and Horsepower Classic Car Show are two of the most popular non-equine activities for guests.

classic red mustang at upperville colt & horse show

On the final day of the Upperville Show, locals drive their beautifully refurbished classic cars to the assigned area on the grounds near the Grad Prix arena. The stunning cars are displayed for all to enjoy and vote on in a friendly “people’s choice” competition. Guests enjoy seeing the popular Thunderbirds, Mustangs, Rolls Royces and an old-fashioned “Upperville” trolley cart owned by one of the board members. The classic car show is a favorite part of the UCHS experience.

vintage car tan convertible coupe packard
vintage car tan convertible coupe packard

What to Wear to the Upperville Horse Show

The week of Hunter Jumper competitions conclude with the popular main Grand Prix event featuring the $216,000 FEI 4* Upperville Jumper Classic. Women wear everything from gorgeous Royal Ascot-style fashions and chic summer dresses to  tailored shirt and designer jean ensembles. The stylish ladies fill the Upperville grounds alongside equally fashionable men. Giving a nod to the summer heat, men often wear polo or neat button-up shirts paired with casual slacks and loafers or perhaps preppy shorts and bow ties or a linen blazer with neat jeans. The ladies accessorize their chic outfits with fabulous hats and wedge heels, sandals or flats. Think practicality when choosing your footwear. The goal is to be comfortable walking on a variety of terrains and standing for an hour or two at the rails to enjoy a better look at the jumpers. Have some fun with accessories. A hat, quality sunglasses and equestrian-themed jewelry for the ladies or a cheeky tie for the gentlemen will set off your outfit nicely. While you are likely to see riders walking around in jodhpurs and tee-shirts, the beautifully dressed spectators bring an air of sophisticated excitement to this cherished historic event.

The 1853 Club

For those with a true passion for the sport of showjumping, joining the 1853 Club is a must. The premiere seating arrangements for VIP guests take place next to the main arena in a gracious long tent. Guests enjoy delicious catered meal service and a bar. Named for the founding year, the 1853 Club takes exceptional care of its patrons. Their sponsorship includes premium viewing and service. The 1853 Club is an exclusive experience and tickets sell out quickly. Spectators are eager to rub elbows with equestrian royalty and to enjoy the best seats overlooking Jumper Ring 1 – the Welcome Stakes, Jumper Classic & Hunter Derby ring.

Tailgating for the Grand Prix

Picnic tables and field parking are available at the Upperville showgrounds for tailgating by reservation. Spectators bring beautiful spreads to picnic under the shade of tents. This area is perfectly positioned to watch the popular main Grand Prix event while enjoying a feast. If you’re planning a stylish Wine & Country tailgate with friends and family, here are some recipes for easy tailgating dishes.

Lawn & Grandstand Seating for Attendees at the Grand Prix Arena

Encircling the Grand Prix arena alongside the 1853 Club and the tailgating tents, are two large grandstands, boxed seating, and lawns for spectators. Admission and parking are free of charge. Horse enthusiasts of all kinds are welcome to enjoy the stunning displays of highly-skilled horses and their riders. The Upperville Colt & Horse Show is a rare opportunity to see such athletic talent.

Surrounded by stunning mountain views and hundred-year-old oaks, older children climb onto the low-hanging boughs to enjoy great views of the competition. The UCHS event is a family-friendly day enjoyed by all.

The First Annual Spirit of the Horse Award

After a week of competitions involving nearly 2,000 horses and riders, the Upperville Colt & Horse Show culminates in the Sunday afternoon Grand Prix. The event kicks off with a speech by the Governor of Virginia. In 2022, the Governor also introduced the first annual Spirit of the Horse award. It is presented by the office of Virginia’s First Lady. The Spirit of the Horse Award honors a local woman who has dedicated their life to the promotion and service of the equine industry. The inaugural winner was Dorothy Lee, board member and 30-year volunteer at the show. The award included an engraved silver bowl, a gift certificate to the current Virginia Governor’s Cup winner (Cana Vineyards in 2022) and a $1000 donation to the award winner’s favorite equine charity.

Get to Know the 2022 Upperville Jumper Classic Winners

The first place winner of the 2022 Grand Prix event featuring the $216,000 FEI 4* Upperville Jumper Classic presented by MARS Equestrian was rider and trainer Schuyler Riley on Robin de Ponthual, owned by Katherine Gallagher. They won $71,280 for the Classic as well as $4,440 for placing 5th in the Welcome Stakes. Riley also rode and placed on Quilimbo, owned by E2 show jumpers and Stakkatos Dollar and Ohara VD Wateringhoeve, owned by Wolfstone Stables & Sales Inc. Riley was both the rider and trainer for all four mounts.

Riley and “Robin” have jumped some big venues around the world, including the FEI Jumping World Cup and Nations Cup Finals. Riley especially loves the spectators at Upperville.

“This arena and this venue are amazing,” she explained. “It reminds me of competing in Europe, where you get a really educated crowd. They know when things go right, they know when things go wrong; they ride every step with you.”

Katherine Dinan placed 2nd in the Jumper Classic on Brego R’N B for $43,200. The team also placed in the Welcome Stakes and the Upperville Two-Phase Stake. Dinan rode & placed on Akita Des Hauts Vents, Athos D’Ell, and Amiro B Z, all owned by Grant Road Partners LLC and trained by Johanna Krӓmer.

Devin Ryan won 3rd on Eddie Blue for $32,400 and placed 10th in the Welcome Stakes. Ryan also rode and placed on Laisha W and Alejandro FCF, all three owned by LL Show Jumpers LLC. He also rode and placed on Hangover owned by Sascha Abramson. Ryan trained all four mounts.

Famous Equestrians at Upperville Colt & Horse Show

The Upperville Colt & Horse Show has a cadre of returning competitors. As the oldest show in America and an important qualifying event for equestrians, UCHS hosts world-famous and Olympic-caliber riders. Notable patrons include the famous General George Patton. Legendary philanthropist, financier and racehorse breeder Paul Mellon regularly attended from his nearby Oak Spring Estate. Joseph Fargis, an Olympic gold medal winner and Hall of Fame member is a lifelong Upperville attendee. Fargis, now in his 70s, is the president of the show. Other award-winning regular attendees have included Kathy Kusner, Rodney Jenkins and Katie Prudent.

The United States’ gold-medal-winning team from the 2018 FEI World Equestrian Games has members that make the Upperville show an annual tradition. This includes the illustrious Devin Ryan (the 2022 UCHS Jumper Classic third-place winner,) McLain Ward, Laura Kraut and Adrienne Sternlicht.

What to Know About the Upperville Colt & Horse Show

Map of the UCHS

upperville colt and horse show

Brand new in 2023, the UCHS is unveiling their brand new Show Office. Located between the Parker Arena and the historic Grandstand, this addition marks only one of several ongoing improvements to the historic Grafton Showground.

Schedule of Events at the UCHS

You can find the schedule of events for the Upperville Colt & Horse Show on their web page. It varies from year to year, but always takes place the first full week of June. For more information, check this page as the date draws near. We will update the gold bar at the top with a current link to the class schedule.

Experience Middleburg While at the Upperville Colt & Horse Show

Middleburg, Virginia, the center of America’s original hunt country is just 5 minutes down the road from Upperville. Competitors and spectators enjoy exploring the quaint town. There are many charming boutiques, farm-to-table restaurants as well as luxury lodging. The National Sporting Life Library and Museum and the Master of the Foxhounds Association are also in Middleburg.

Wineries to Visit Near Upperville

If you’re a wine aficionado, you’ll want to explore some of the 50 wineries that are in the Middleburg area. Start with Greenhill Winery & Vineyards. This winery has its own polo team and participates in Virginia United Polo. Another must-visit destination for oenophiles is Cana Vineyards & Winery, the winner of the 2022 Virginia Governor’s Cup. Melanie Natoli is the first female winemaker to win the modern-day Governor’s Cup competition. She won the grand prize with her 2019 Unité Reserve while the 2019 Le Mariage racked up a gold medal and five other Cana wines earned silver medals. Also worth a wine-tasting trip is 50 West Vineyards—their 2019 Ashby Gap earned a gold in the 2022 Virginia Governor’s Cup. RdV Vineyards is another exceptional winery to visit in the area.

Shopping Near Upperville

If you prefer shopping to sipping, head to the charming village of Middleburg to find one-of-a-kind treasures. Mystique Jewelers offers custom designs, several elegant jewelry brands and a beautiful equestrian jewelry collection. Antiques on Washington Street features English, European and American furniture and a large selection of Staffordshire dogs. The Middleburg Antique Gallery curates English and Scottish furniture and a little bit of everything else with more than 40 dealers under one roof. For unique home décor and stunning gifts from around the world, visit style maven Terri Pakravan’s Atelier Design and Décor. You will find everything from fine art to statement jewelry.

Places to Stay Near Upperville

There are plenty of places to stay and dine in Middleburg, from the Red Fox Inn to the Salamander Resort and Spa, a five-star equestrian-themed luxury lodging. Not only is The Salamander a sponsor of the Show, but they house many of the visiting out-of-town equestrians, as well as their horses in the on-site stables. There are ample Virginia horse trails nearby to explore with your mount. The historic Goodstone Inn & Restaurant, just ten minutes from the center of Middleburg, is a lovely property to relax and unwind between competition days. The luxury inn offers private cottage stays, traditional inn rooms, a spa and exceptional fine dining. The expansive farm property provides many experiences, growing much of the flowers, vegetables and fruits they use in their restaurant.

More Equestrian Events in Virginia


Virginia steeplechase races are a popular annual tradition. Learn more about the Virginia Gold Cup Horse Race, the The International Gold Cup Races, Foxfield Races and the The Montpelier Hunt Races from Wine & Country Life. Virginia is also home to the Virginia Horse Center in Lexington. The Center hosts diverse events from dressage to vaulting and barrel racing.


Virginia showjumping may have started at the Upperville Colt & Horse Show, but it didn’t stop there. In September, the Middleburg Classic Horse Show and the Piedmont Jumper Classic are also held at the Grafton and Salem Farms Showgrounds. Smaller events are found around the state and include established shows in Warrenton, Bluemont and Culpeper.


Polo makes its home in both Northern and Central Virginia. Teams of 4 athletes and their mounts race across the field attempting to score points by hitting balls through the goalposts. This sport requires endurance, strength, and pinpoint training. Read more about Virginia polo by following the links for Roseland Polo at King Family Vineyards, championship-winning college teams at the University of Virginia Polo Club, and the United Virginia Polo League in Northern Virginia.


Colonel Dulany’s contribution to the horse world did not stop with the Upperville Colt & Horse Show. He also founded Upperville’s Piedmont Fox Hounds. This was a similar attempt to bring attention to a sport and bloodline that were in danger of becoming unappreciated. Today, Piedmont Fox Hounds is a private hunt club, but many other such clubs have rallied to continue the tradition of foxhunting. Although originally these hunts were to keep invasive predatory species such as foxes, bobcats and coyotes in check, these days there no actual intent to bring in a catch at the end of the day. For those who dislike even that aspect, there are also “drag hunt” meets. At a drag hunt meet the dogs will follow a false trail laid down by a volunteer pulling a scented sack over the prescribed route.

Upperville Grand Prix 2022

There is something for everyone at the Upperville Colt and Horse Show. Even the most novice of spectators enters into the spirit of grace, enthusiasm and sportsmanship displayed. Upperville is referred to as the oldest and most unique horse show in the United States, and also as the one with the most “heart”. Upperville is the place where riders treat each other like family while staff, volunteers and spectators welcome each other back with joy. There is nowhere quite like Virginia Horse Country and the Upperville Colt & Horse Show, and they give us the chance to remember that Under The Oaks for a full week each year. ~

MAI LIONNI GUSS is an associate editor at Wine & Country Life. She holds multiple degrees in literature and Shakespeare and has a boundless enthusiasm for exploring the life and style of Virginia’s wine country. 

R. L. JOHNSON is our co-publisher and creative director. She began her career after graduating ArtCenter College of Design as a professional photographer in Los Angeles before moving into graphic design and art direction when she relocated to Charlottesville in 1994. As our company’s co-founder and visionary, she enjoys all aspects of the publishing process from story conception to graphic design to photography.

Virginia Wine & Country celebrates elevated living in Virginia Wine Country. Virginia Wine & Country Life is a semi-annual luxury print magazine with a full digital presence. The Virginia Wine & Country Gold Book is an annual guide to the top award-winning wines, wineries and experiences in Virginia Wine Country. The annual Virginia Wine & Country Wedding Planner is an art book of elegant Virginia weddings. Virginia Wine & Country tells the stories of Virginia wineries, the farm-to-table movement, luxury travel, entertaining, art and the elegant country lifestyle. Ivy Life & Style Media also provides branding, web design and PR services for the wine industry.