This under the radar town in Florida has become a playground for the richest of the rich

New York Weekend Edition /
Jan.January 15, 2017 10:30 AM

Every winter, the small town of Wellington, in southeast Florida, experiences a tremendous influx of some of the wealthiest people in the world.

From the Springsteens to the Bloombergs, to the families of Steve Jobs and Bill Gates, to Arab sheikhs and South American billionaires, it’s a congregation of people with spectacular quantities of money.

No, they aren’t gathering for some sort of business affair. They’re coming for WEF: the Winter Equestrian Festival, which takes place every year from January to April on the hallowed grounds of the Palm Beach International Equestrian Center. The 12-week WEF has been the longest equestrian event of its kind for several years running, and it attracts riders at all levels of the sport.

Because of the costly nature of all things equestrian, it’s no surprise that rich people and horses go hand in hand. But while some wealthy riders and owners are just in it for the glamour and prestige, some — like Georgina Bloomberg and Jessica Springsteen — are serious and successful competitors.

As WEF has grown over the years, it has turned Wellington into a winter oasis for the upper crust, who come to ride, mingle, and bask in the warm weather. But while the human amenities are nothing to sneeze at, the real luxuries are reserved for the horses. Here’s an inside look at this star-studded fantasy world, where celebrities come to play and their four-legged companions reign supreme.

Wellington, Florida, is a community of about 60,000 people in southeast Florida, about 15 miles west of West Palm Beach. And without a doubt, horses rule in Wellington.


Bill Gates owns several properties in the area, and in 2016 he reportedly completed a $38 million purchase of An Entire Wellington Street, totaling six properties and about 20 acres. His daughter Jennifer is a seasoned WEF competitor.


In a fitting continuation of the rivalry between Gates of Microsoft and the late Steve Jobs of Apple, Laurene Powell Jobs reportedly purchased a 3.5-acre ranch on Wellington’s Quarter Horse Trail for $15 million in July 2016. Her daughter Eve is also an accomplished rider and has competed against Jennifer Gates.


Grand Prix Village, an exclusive, horse-focused development within walking distance of the show grounds, is famous for stables that look like this.

Gorgeous stables… #GrandPrixVillage #Wellington #Florida #USA

A photo posted by Magali Perez (@mag_prz) on

The festival takes place on these sprawling grounds, which include 18 competition arenas and 256 permanent horse stalls.

More than 5,000 horses with a net value of well over half a billion dollars compete within the circuit.

Congratulations to this week’s WEF Champions… #wef2016

A photo posted by Winter Equestrian Festival (@esp_wef) on

Jeremy Jacobs, billionaire owner of the Boston Bruins and chairman of Delaware North, used to effectively rule the Wellington scene from his 21,000-square-foot mansion on the sprawling Deeridge Farm.

Amazing #aerial shot of #deeridgefarms, home of the brand new venue for the #wellingtonmasters in Feb. 2016!

A photo posted by Palm Beach Masters (@pbmastersevent) on

But then, in 2006, a wealthy Boston developer named Mark Bellissimo arrived on the scene and bought the Palm Beach International Equestrian Center for $135 million. He’s still the owner and has expanded the festival into the grand event it is today.

Looking forward to the Grand Prix tonight #pbiec #wellingtonflorida #igerswestpalmbeach

A photo posted by Karin (@famousstylist) on

Fancy boutiques can be found along the horse paths that connect competition rings and practice areas on the show grounds.

Flashback to our Spring pop-up store @winterequestrianfestival. #SS16′ #jacandjay

A photo posted by JAC + JAY (@jac_and_jay) on

Events at WEF are often sponsored by luxury brands. Hermes’ line of horse products includes saddles that cost around $8,000.

The horse with no name #SautHermes

A photo posted by Hermès official account (@hermes) on

Famous names and faces are common in the competition rings. Here, Georgina Bloomberg celebrates a good round in a Nations Cup event. Bloomberg is the 33-year-old daughter of former New York City Mayor Michael Bloomberg and Susan Brown.

Jessica Springsteen, daughter of rocker Bruce, and her horse Cynar VA sail over a fence while judges watch.

Actor Tom Selleck’s daughter, Hannah, dresses up as Alice in Wonderland to ride in a competition for charity.

As if the majorly rich weren’t wealthy enough, prize money for some of the events at WEF can top $500,000.

Riders in traditionally glamorous white competition clothes prepare for their class by walking a course of jumps. A high-end competition outfit can easily cost upward of $1,000.

The horse show grounds are not the only place to host high-profile guests in Wellington. Prince Harry has been known to play in polo matches at the nearby International Polo Club.

Even President-elect Donald Trump has tried to get in on the action. In recent years, he has hosted the Trump Invitational show jumping event at Mar-a-Lago, his Palm Beach property that’s located within a few miles of the Wellington community. Here, he poses in front of a jump with country singer Hunter Hayes.

Hunter Hayes gets the Trump thumbs-up from the Donald himself. #trumpinvitational

A photo posted by Horse & Style Magazine (@horseandstylemag) on

As crazy as “Welly World” is, though, the horses really do come first. Owners spend a tremendous amount of money to ensure that their equine companions can perform their best in competition. Here, a horse and rider train in front of an equine palace.

Tina’s kinda a big deal tho ✈️ PC: @sofiepousette

A photo posted by Sport Horse Lifestyle™ (@sporthorselifestyle) on

Related Articles

Matt Lauer exposes Hamptons estate to the market
Matt Lauer exposes Hamptons estate to the market
Matt Lauer exposes Hamptons estate to the market
 Fredrik Eklund and the property (Getty, Steve Frankel)
Fredrik Eklund lists Bel Air mansion for rent as family moves to “forever home”
Fredrik Eklund lists Bel Air mansion for rent as family moves to “forever home”
Gordon Ramsey and his Lucky Cat restaurant (Lucky Cat)
Gordon Ramsay to open first South Florida restaurant in Miami Beach
Gordon Ramsay to open first South Florida restaurant in Miami Beach
From left: Ace Hotel’s Brad Wilson and Omnia Group's David Paz along with 225 Bowery (Getty, Google Maps, Ace hotel, Omnia Group)
Bowery micro-hotel facing foreclosure files for bankruptcy
Bowery micro-hotel facing foreclosure files for bankruptcy
200 Park Avenue and Tishman Speyer's Rob Speyer(Tishman Speyer, Getty)
MetLife Building gets the luck of the Irish
MetLife Building gets the luck of the Irish
A photo illustration of Blackstone's Jon Gray (Getty, Blackstone)
Blackstone ramps up tenant evictions
Blackstone ramps up tenant evictions
10 Riverside Boulevard (One Waterline Square, Getty)
Holiday hangover: Manhattan’s luxe market is stuck
Holiday hangover: Manhattan’s luxe market is stuck
3 Riverside Drive (Google Maps)
Won’t anyone buy this Upper West Side mansion?
Won’t anyone buy this Upper West Side mansion?

The Deal's newsletters give you the latest scoops, fresh headlines, marketing data, and things to know within the industry.