Bespoke Living Travel, Food & Drink

A Guide to Three of the World’s Top Equestrian Events

Plus five spectacular estates for celebrating or preparing to compete in such elite competitions

Around the world, equestrian competitions take place in a wide range of settings, from the elegant Kentucky Derby at Churchill Downs, to the rugged Nevada and California wilderness of the Tevis Cup. Horsemanship can be choreographed and precise, as in dressage; thrilling and lightening-fast, as in the Kentucky Derby or the Belmont Stakes; and it can be almost acrobatic, as in competitive show jumping. Each of these different kinds of equestrian disciplines has its own architecture and design, and the horses who compete in them require different kinds of facilities: some benefit from hydrotherapy and walking on cushioned treadmills, while others need to practice galloping on uneven terrain for cross-country eventing. There are exceptional estates with facilities for every different kind of horse and rider, and all riders find inspiration in the world’s most important equestrian competitions, from the Derby to the Olympic Games.

The Kentucky Derby 
The first Saturday in May, all eyes in the equestrian world are trained on Churchill Downs in Louisville, Kentucky. Since 1875, the famous track has hosted the
Kentucky Derby, possibly the most famous thoroughbred race in the world. Each year, the Derby winner has a chance to claim the coveted Triple Crown—a rare honor bestowed on the horse that wins the Kentucky Derby in Louisville, the Preakness in Baltimore, and Belmont Stakes near New York City.

In 2015, American Pharoah won both the Triple Crown (the first to do so since 1978) and the Breeders’ Cup Classic in Lexington, Kentucky, making it a banner year for equestrian enthusiasts. The winner each year usually finishes in just over two minutes—what some have called “the most exciting two minutes in sports.”

For many who watch the event from the comfort of home, throwing a Derby party is an annual tradition. Castle Post in Versailles, Kentucky, is a spectacular estate that provides a prime setting for a truly memorable Derby party. Located about an hour west of Louisville near Lexington, Castle Post is nestled in a region that’s home to some of the world’s top horse farms. Its history as a renowned inn has led members of royalty as well as celebrities to stay in its well-appointed rooms. Two full residences are also on site. A grand staircase, banquet room, and rooftop with stunning views plus professionally landscaped grounds combine to make Castle Post a magical place for gatherings of just about any size and type. Horse boarding and training facilities are available at numerous equestrian outfits in Versailles and Lexington.

The Olympic Games in Rio de Janeiro
In August 2016, more than 10,000 athletes from 206 countries will compete in Rio de Janeiro, Brazil, at the first Olympic Games ever held in South America (the only other Latin American host was Mexico City in 1968). Each of the three equestrian sports, dressage, show jumping, and three-day eventing, showcase different skills on the part of both horse and rider.

Dressage has its roots in military exercises dating back as far as horsemanship itself. Before the advent of modern warfare, horses played a crucial role in battle that required precise movements and strict obedience. In contemporary dressage competitions, riders are judged on their ability to lead their horses through complex tests of agility with grace and coordination.

While casual observers might think a horse is doing all the work in a dressage demonstration, the rider is actually communicating subtle cues and instructions through shifts in weight and almost imperceptible heel taps. At the Olympic Games, riders compete at the Grand Prix, which involves delicate maneuvers like the pirouette. 

Dressage training requires the right setting and special facilities. Red Horse Farm in Mashpee, Massachusetts, situated on nearly 7.5 picturesque acres, was designed and built with dressage in mind. In addition to its large outdoor arena, it boasts a heated indoor arena with skylights and custom riding surfaces, stables for several horses, an automatic watering system, grooming areas, and hay and grain storage.

Designed around equestrian pursuits, Red Horse Farm in Mashpee, Massachusetts, has the facilities to train champion horses.

Show Jumping
In show jumping, horses and riders must leap over high fences, sometimes in quick succession. Practice gyms are important in the training of show jumpers, who are at risk of serious injury when they encounter uneven terrain. These elaborate gyms include the sort of equipment one might expect to find at any state-of-the-art fitness center including shock-absorbent treadmills with inclines and even swimming pools—all scaled for four-legged athletes.

In Mexico City’s Federal District, the Cuadra San Cristobal estate is a brightly colored oasis designed by Pritzker Prize–winning architect Luis Barragán. The grounds—which are full of unexpected visual delights featuring bold, saturated colors—house stables as well as a professional training ring. There are also two swimming pools, the larger of which was designed just for horses. Hydrotherapy is an increasingly popular method of providing horses with low-impact exercise, which is especially beneficial in cases of injury or joint pain.

With an architectural plan that seamlessly connects the interior of the home with its lush exterior grounds, this four-bedroom residence is ideal for nature lovers with a flair for contemporary design.
With an architectural plan that seamlessly connects the interior of the home with its lush exterior grounds, this four-bedroom residence is ideal for nature lovers with a flair for contemporary design.

Three-day eventing is the triathlon of the equestrian world. It includes events drawn from the repertoire of both dressage and show jumping, with the addition of a tough outdoor course full of natural obstacles as well as water and uneven terrain. Successful event horses have a mixture of the qualities that make champion jumpers and dressage competitors, plus the endurance to gallop long distances between jumps, focus, and then gallop on to the next jump with throngs of competitors lining the course, as in a golf tournament, and cheering them on. Eventing is the preferred Olympic equestrian event of the British Royal family, and two members of the House of Windsor have represented Great Britain at the Olympics in this respect. Princess Anne competed in the 1976 Olympic Games in Montreal, Canada, and her daughter, Zara Phillips, won a silver medal as part of the British eventing team at the London Games in 2012. She will also compete in Brazil later this year.

June Farm in Surrey, England, about 45 minutes south of London, includes a 17th-century home that has been fully updated while retaining its English country charm. With fully irrigated gardens, a greenhouse, and a pool with pool house, June Farm also has superb equestrian facilities that include an American-style barn, multiple paddocks, a hay barn, and a sand school for training.

The Tevis Cup
A far cry from the genteel traditions of the Kentucky Derby, the Tevis Cup, also known as the Western States Trail Ride, is a rugged, 100-mile race on horseback across the Sierra Nevada mountains that follows a trail originally taken by silver and gold prospectors in the 1850s. Riding 100 miles in 24 hours would be challenging under any circumstances, but the Tevis trail takes horse and rider through untamed wilderness with steep hills to navigate.

Wildlife encounters are also common. The Tevis Cup is usually scheduled to coincide with the full moon in late July as nearly half of it takes place at night. Competitors ride at almost 9,000 feet above sea level and sometimes traverse narrow trails with sharp drop-offs. Because of the physical challenges of the Tevis Cup, prospective riders must meet the endurance riding qualifications set out by the Western States Trail Foundation, which organizes the race. More than a dozen veterinary checkpoints along the way ensure each horse is fit to continue. Each competitor who completes the trail within 24 hours is awarded a well-earned silver Completion Award Buckle.

For riders who love the rugged beauty of the California desert, the Stone Canyon Ranch set on 10,000 acres in Paicines, California, offers both state-of-the-art equestrian facilities and natural surroundings. Unobstructed views of the nearby mountains of Pinnacles National Park and the property’s unique stalls, paddocks, and training rings complement the house itself, a modern masterpiece by architect Ugo Sap.