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How a Sleepy Florida Town Became the Horse Riding Capital of the World

The who's who of the international equestrian set descends on Wellington every winter.

British show jumper Ben Maher in the Wellinton ring. Elena Lusenti

Near the start of this year’s annual winter equestrian season in Wellington, Fla., a playdate for the under-five set is underway at Rushy Marsh Farm, one of the nicest properties in the Grand Prix Village, an exclusive area of luxuriously equipped stables. Since the lush, generous grounds of Rushy Marsh belong to Frank McCourt—a businessman who owned the Los Angeles Dodgers before selling the team in 2012 for a record $2 billion—and his second wife, Monica, this is not your ordinary playdate of Legos and grilled-cheese sandwiches.

Members of the staff, who seem to outnumber the guests and their young children, wear Rushy Marsh polo shirts as well as tiaras fashioned from pipe cleaners. They pass red velvet bundt cakes from the nearby bakery Nothing Bundt Cakes and assist tots making their own pipe-cleaner headwear at an arts and crafts table. There are real miniature horses to pet and inflatable unicorns with which to wrestle across the expansive lawn. A taco truck serves organic tacos and watermelon-lime and tamarind-basil aguas frescas.

In Wellington, a patch of what was once farmland 15 miles from the exclusive enclave of Palm Beach Island and the Atlantic Ocean, every day is kind of a play date—for adults and for their offspring. From mid-December to late April, around 2,500 riders and 7,500 horses descend on Wellington to make the Winter Equestrian Festival the headquarters of the horse set. Some of the world’s wealthiest families congregate here for five or so months before dispersing to less concentrated events around the US and in Europe, where riding and jumping competitions are more popular and televised.

The stables at Ashland Farms in Wellington

The stables at Ashland Farms in Wellington  Elena Lusenti

But entrepreneurs, including one who has arguably made Wellington the equine epicenter it is, are attempting to capitalize on the buying power of the horse world and both draw on and draw away from the town’s enormous popularity. Mark Bellissimo, who turned the village into a lifestyle destination, is attempting to replicate his winning formula in remote Tryon, N.C., while rivals Larry and Roby Roberts are set to open their lavish World Equestrian Center 250 miles north of Wellington in Ocala in 2021. Whether either enterprise will succeed in luring stalwarts remains a much-debated question, so entrenched is Wellington in America’s equine culture.

“I don’t think Wellington is ever going to have a lot of competition from Ocala,” says one serious rider. “Wellington is right there in Palm Beach [County]. Ocala is in the middle of nowhere. [In Tryon], if you leave the showgrounds, there’s no food, and few hotels.”

“When I started going in 1998, the horse show was nothing like it is now,” says Georgina Bloomberg, who, in addition to being a world-class rider, is an investor in the Wellington Equestrian Center. “It’s exploded. I’d say now that 75 percent of people [in the horse world] will give you Wellington as their mailing address.”

And Bloomberg is not talking about only Americans. “You now see a cross section of nationalities and cultures,” says rider Arriana Boardman, who has witnessed Wellington “evolve tremendously” over the 20 years she has been competing here. “It’s male and female, young and old, seven to 70. It’s a group coming together with a shared passion for riding and to be a part of that sport in good weather. It would be hard to achieve that in any other place in the world.”

Junior riders walk and hop in equitation class

Junior riders walk and hop in equitation class  Elena Lusenti

The McCourts met in Los Angeles before trading life there for South Florida. “I fell in love with her first, and then horses,” says Frank, a longtime real estate developer. When they met, the new Mrs. McCourt, a statuesque brunette who grew up in Texas, was interested in riding only as a hobby. “Frank bought me my first jumper,” says Monica, referring to a particularly athletic kind of four-legged animal. (The best jumpers can cost in the millions, but a $50,000 specimen can win any night of the week.) She dragged her husband to Wellington on a scouting trip, and they decided to move there.

Now the McCourts are in the horse business. They own the Miami Celtics, a show jumping team that includes Jessica Springsteen, Bruce’s daughter, who keeps her horses at Rushy Marsh. The Celtics compete as part of the Global Champions League, a leading international equestrian circuit. The McCourts purchased half of the league itself in 2014 with the hopes of transforming it into the World Cup or Formula One of horse jumping. What’s more, the McCourts and their three-year-old daughter, Luciana, all ride together.

“He’s type-A, all business and 64,” says Monica, who alternates between English and Spanish with some regularity. “But I’ve got him jumping!”

And, of course, there is the socializing that happens before and after the riding. “We have parties like this all the time. The kids are so happy,” she says, not seeming to mind that her pristine white Gucci sneakers are in imminent danger of getting ruined by her farm’s muddy fields. “Wellington to me has the social, the sport and the sun. You can’t beat it.”

LONDON, ENGLAND - AUGUST 13: Monica Algarra (L) and Frank McCourt attend the 2014 Longines Global Championships Tour party at Claridge's Hotel on August 13, 2014 in London, England.

Monica and Frank McCourt  David M. Benett

Horses are the Wellington community’s lifeblood—so entwined in its everyday rhythms that residents seem to hardly take notice of the perfectly manicured paddocks, bucolic wooden fences and yellow street signs that read: “Slow. Horses have right of way.” “This is not a sport, it’s a life. It’s one of the largest industries hidden in plain view,” says Danielle Levine, who in 2017 started Kaval, an e-commerce company she hopes will become the Net-a-Porter for the horse set.

“We often joke when you live there for the winter, you don’t really leave the five-square-mile radius for weeks on end,” says Adrienne Sternlicht, another world-class jumper who started competing as a child in 2002.

Sternlicht, the daughter of Barry Sternlicht, the chairman and CEO of Starwood Capital Group, spends the spring and fall in New York and usually competes in Europe over the summer, where shows are prestigious and lucrative and can attract 60,000 spectators. Other riders might go to horse shows in Old Salem, N.Y.; Devon, Pa., and Kentucky in May and June; the Hampton Classic in August; then to Kentucky again and to indoor competitions in places such as Washington, D.C., in the fall, before heading back to Wellington to start it all over again. Serious riders “follow the money and FEI qualifying ranking points,” Sternlicht explains. (The FEI World Equestrian Games, managed by the Fédération Equestre Internationale, are held every four years, between Summer Olympics.)

Georgina Bloomberg Winter Equestrian Festival, Wellington, USA

Georgina Bloomberg competes in the Winter Equestrian Festival  Shutterstock/Mediapunch/REX

In the context of that intensely competitive circuit, Wellington “is like Disneyland,” says Bellissimo, the most prominent impresario behind the area’s explosive growth. He grew up in Massachusetts, then went on to attend Andover, Middlebury and Harvard. He became a kind of turnaround entrepreneur: in the family food service; in technology, distributing Japanese back-up truck alarms; in the health-care and medical fields; and eventually with a sales-force company called Brandwise. In the late 1990s, his daughters started horseback riding, which eventually involved weekend trips to compete in Wellington.

When horse shows started in the US, they were on private estates with indoor rings in affluent locales such as Locust Valley on Long Island; eventually they became too large of a business and moved to bigger venues, including Devon and even Madison Square Garden, where attendees wore white tie. Since the 1970s, amateur and professional horse people alike have wintered in Wellington, in part because it is conducive for competition. The weather is warm and the footing safer than the hard soil up north. By the early aughts, the Wellington circuit consisted of a five-week competition without the accouterments of fancy seating or sponsorship funds. Bellissimo saw the potential for growth.

In 2006, along with a few partners, Bellissimo bought the showgrounds alongside 200 acres of land and gained control of the Winter Equestrian Festival. He extended the competition season to 12 weeks, developed an arena with 7,000 seats and 2,500 stables, and encouraged local community attendance with free general admission, a carnival atmosphere and Jumbotrons. It grew to include not only hunter/jumper competitions and polo, but also dressage (a kind of horse ballet). His goal: to develop the area from “a horse show into more of an equestrian lifestyle destination,” he recalls. “When I first mentioned the idea of an equestrian-lifestyle destination, nobody knew what that meant. For me, it meant great hospitality, great entertainment and great commerce.”

Pony riders at the so-called Pony Island await class results

Pony riders at the so-called Pony Island await class results  Elena Lusenti

And, of course, horse lovers eager to have more of the same for neighbors. “It used to be a charming little place to show, but Bellissimo brought it to a global level,” says Kelly Klein, a photographer and longtime equestrian who gave up competing in the ring for a different kind of competition, namely local real estate. Klein, who has chosen to live by the beach instead of in Wellington, has flipped at least three houses in the area. “The market will always remain strong. Now everybody from all over the world comes. He really does it in a big way. It’s not a place to come to la-dee-da around.”

When he started expanding the reach of the horse show, “I thought people would have a greater interest in buying homes and farms,” says Bellissimo, who now owns 880 acres, a publication called The Chronicle of the Horse and Wellington’s International Polo Club. The idea was that the horse show would be the main attraction. Or, as he puts it, “The horse show was really the oceanfront or the golf course: The closer the proximity, the more valuable it would be.”

On a Saturday night in March, a crowd of thousands descends on the Winter Equestrian Festival for the weekly Grand Prix. This one, sponsored by real estate company Douglas Elliman, has a total purse of $391,000. Bloomberg, riding a horse called Chameur 137, eventually places 14th this evening; Springsteen, riding Fleur de L’Aube, places 22nd.

The trophy room in Kent Farrington's barn

The trophy room in Kent Farrington’s barn  Elena Lusenti

Many of the locals come as if dressed for a baseball game, in message T-shirts and baggy shorts. They eat tacos, French fries and pizza from stands and food trucks before taking their free seats in the rafters. But most spectators arrive attired in an understated, low-key elegance—crisp button-downs, Louis Vuitton Neverfulls. One attendee describes the look as “rich people slumming.”

Before the competition, and during lulls, they browse the permanent Hermès shop on the grounds, or for jewelry, such as a $680,000 blue-diamond bracelet at Lugano. (The owner’s brother is in the equestrian world.) Some 1,200 heavy hitters on the circuit have regular ringside tables at the private International Club on-site—costing in the tens of thousands for a season—which offers Saturday evening buffet dinners with such selections as prime rib and crab claws.

Wellington is “the area to be, because there’s no place else,” says Robert Ross, a former Grand Prix jumper turned real estate agent in the area who recently started Robert-Squared, a line of vegan tack wear, with his husband, Robert Dover, an equestrian who competes in dressage. Thanks to local restrictions, hotels in Wellington are only recent developments and limited to a Hampton Inn and a Fairfield Inn at that, so owning or renting real estate tends to be a necessity.

Mark Belissimo

Mark Belissimo 

At the upper echelon of property are farms. Years ago, “there were only a couple permanent farms,” says Bloomberg. That’s no longer the case. Farm owners such as Bloomberg, daughter of billionaire and former New York mayor Michael Bloomberg, have the luxury of practicing whenever they choose and in their own environments rather than on the actual showgrounds.

“It’s like having a private skating rink versus going to the public skating rink,” says Holly Peterson, who recently published a book, with Assouline, called Wellington: The World of Horses. The daughter of the late investment banker Pete Peterson, Peterson’s own daughter is a competitive rider.

Farms in Grand Prix Village—owned and operated by the likes of the McCourts, BET cofounder Sheila Johnson and Athina Onassis—are currently on the market for between $8 million and $14 million. A lot is not big enough for both a 20-stable barn and a large house, so typically an owner keeps only grooms accommodations there and lives elsewhere, such as the Palm Beach Polo Club, a 2,200-acre stretch with a golf course, a clubhouse and 24-hour roaming security. The Polo Club’s various neighborhoods offer everything from modestly priced $250,000 condos to $20 million estates.

For prime properties with both stables and homes, there’s Mallett Hill, where the Bloombergs, the Jobses and the Gateses all own residences. Bill Gates, whose 23-year-old daughter, Jennifer, is a competitive rider, slowly bought out five of his neighbors to own an entire street. Homes in the development rarely come on the market. One four-bedroom is currently listed at $15 million, another at $23 million.

WELLINGTON, FL - MARCH 30: Jessica Springsteen during the $35,000 Bainbridge 1.45M Classic at the Winter Equestrian Festival on March 30, 2018 at The Palm Beach International Equestrian Center in Wellington, Florida. (Photo by Aaron Gilbert/Icon SportsWire)

Jessica Springsteen  Icon Sportswire/Getty Images

And then there are the horses. To be competitive, a rider needs more than one, and a really good horse can cost $100,000 or more. Plus the costs of a trainer, housing, feed, a veterinarian and shipping (sometimes via Fed-Ex) of said horses. (No, riders don’t box up their animals; usually horses travel via chartered planes.) On the low end, the total annual horse expenses hover around $60,000. Most competitors—even those with famous family names—have wealthy sponsors, who then share in competition winnings.

The redevelopment of Wellington has been such a success that Bellissimo has been at work building an area for similar purposes in Tryon, with mixed results. The World Equestrian Games there last fall were beset with problems, some related to Hurricane Florence, some owing to a lack of preparedness. Bellissimo, though, as you would expect, is the voice of confidence. If Wellington is like Disneyland, he says, “Tryon is more of a Disney World. We bought 1,600 acres and have master-planned the environment.”

His hope is that in two years, Tryon will be a resort destination with lodging, trade shows and art festivals. Horse people, however, are very skeptical, to put it mildly. “It’s a disaster,” says one. “No one is going to want to spend July in Tryon.”

Jennifer Smith's dogs at Green River Farm

Jennifer Smith’s dogs at Green River Farm  Elena Lusenti

“I gather the facility is a lovely one, but I found that the location wouldn’t really translate to our life,” says Boardman, a bit more diplomatically.

Bellissimo is also dealing with personal troubles. He recently filed for divorce from his wife of 30 years, Katherine, which apparently surprised few but nevertheless raised concerns about the business’s future. One regular on the circuit says Bellissimo was not seen much around the Equestrian Festival this season, that perhaps his power in the area may be dwindling, though another assures that there are enough influential stakeholders that Wellington will not suffer.

One complaint about the Equestrian Festival is that its outward-facing image may be one of luxury and wealth, but behind the scenes, it’s bursting at the seams and could use some improvements. Parking is a “nightmare,” says one observer. Some dirt roads are so overpopulated by cars, motorcycles, horses and dogs that it’s like a chaotic city center, adds another, who also feels the on-premises stables need a makeover.

Polo ponies cool off after playing in the Florida heat

Polo ponies cool off after playing in the Florida heat  Brittany Brett

Meanwhile, a three-week competing mini-circuit called the Palm Beach Masters at the 300-acre Deeridge Farms (owned by Jerry and Peggy Jacobs) has begun to steal a bit of Bellissimo’s Wellington thunder. Entries there are limited to 350 horses, and footing in the two rings is state of the art. The facility is “not being overused,” says a knowledgeable insider. “So it tends to be a little more, I guess, luxurious.” The food, he adds, is also much better: “Last year they had Iron Chef Morimoto.”

The goal, according to Dan Carr, the CEO of the Palm Beach Masters, is to attract a more European crowd. “It’s very upscale; it’s very horse-minded,” he says. “You need to earn your spot to be there. It gives the sensation to the rider and the exhibitor that it’s special.”

The Wellington community is also paying attention to expansion in Ocala, a city an hour from Orlando that bills itself as the “Horse Capital of the World.” A show run by H.I.T.S. (Horses in the Sun, which also manages shows from Virginia to California) boasts purses in the million-dollar range, much higher than Wellington’s. Another nearly week-long horse show called the Live Oak International, sponsored, like many of these events, by the Swiss watchmaker Longines, provides points for World Cup qualification. Over one March weekend, some riders competed in Wellington, then hopped on private jets to compete in Ocala that same day.

Arriana Boardman and her daughter, Olympia

Arriana Boardman and her daughter, Olympia  Elena Lusenti

Come 2021, the city will welcome the World Equestrian Center, adjacent to the Golden Ocala Golf & Equestrian Club. Modeled after another World Equestrian Center in Wilmington, Ohio, it will feature a five-star hotel, 1.5 million square feet of indoor and outdoor riding space and an on-site chapel.

“We’re not looking to compete [with Wellington]. We’re setting our own standards,” says Roby Roberts, the WEC’s CEO. “We think the facility will speak for itself and tell its own story.”

Even with climate-controlled barns and an on-site veterinary clinic, the WEC will be challenged to replicate the exclusivity of Wellington, where members of the community often zip over to the showgrounds on golf carts inscribed with their first names or family logos.

The country-club atmosphere and perpetual social calendar is part of the allure, as is the primacy of horses. “We don’t want families to feel like they’re under a microscope,” Bellissimo says. “The fabric of that is very important so that major businesspeople and celebrities can feel like it’s a safe haven, that they’re enjoying their family. That’s a product in and of itself.”

The Hermès boutique at the Wellington showgrounds

The Hermès boutique at the Wellington showgrounds  Elena Lusenti

There’s an almost homespun feeling. “One of the things that’s interesting about Wellington is that things here don’t really change,” says Alexa Weeks Pessoa, an American show jumper whose equestrian husband, Rodrigo, is an Olympic medalist from Brazil.

Could Tryon or Ocala grow into the next Wellington? Sure, it’s possible, says Bloomberg. “But it would take a long time. Wellington is 30 years in the making. You can’t just throw it down somewhere.”

It also offers easy access to New York City. Plus, there is the benefit of swanky Palm Beach. Wellington is only a short drive to the ocean. (Ocala is an hour and a half to the nearest body of water.) There is, indeed, still a divide between insular Palm Beach society on the island and the insular Wellington scene. The twain don’t often meet. “I tell my friends on the island that we’re over in Wellington, and they say, ‘Where’s that?’” jokes the film producer Daniel Crown, whose daughter, Alexandra, studies at the University of Miami so that she can practice and compete in Wellington all week.

Real estate broker Carol Sollak, of the local branch of Engel & Völkers, has been in the area since 1978 and says it’s not unusual for a client to own a farm in Grand Prix Village, a home in the Polo Club and a separate house on the island. “This is a clientele that has houses all over,” she says. “Often the husband will say he likes the ocean.”

That’s why the McCourts also bought a home on Palm Beach’s Billionaire’s Row, which, according to reports, includes 320 feet of beach frontage and set them back $77 million. “This way,” Monica McCourt explains, “we get the best of both worlds.”

Wellington: The World of Horses‘

The images in this feature are from the book ‘Wellington: The World of Horses‘ (Assouline, 2019), by Holly Peterson, photography by Elena Lusenti.

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