In The Saddle With Elliman's Kay Lawson

Kay & The Classic

Kay Lawson of Elliman at The Hampton Classic Horse Show in Bridgehampton. Independent/Gordon M. Grant

Douglas Elliman’s equestrienne Lawson combines real estate and riding to form a specialty all her own

“No hour of life is wasted that is spent in the saddle.” Winston Churchill.

For those who grew up here, going to the Hampton Classic is like seeing a dear old friend.

With 1600 horses, a VIP tent that holds 3000 guests, and 50,000 spectators over the course of the show — which this year runs through September 2 — as well as over 100 vendors, the Hampton Classic has a major local economic impact of over $95 million annually, and since 1977 has contributed $2 million to its official partner, Stony Brook Southampton Hospital.

Unlike many horse shows, the Hampton Classic is a 501(c)3 non-profit organization and broadens its charitable mission by partnering with local nonprofits and equestrian-related charities in everything from its Animal Adoption Day — where you often see animal rights ambassador Georgina Bloomberg and other riders interacting with the dogs, cats, and rescue horses to find them homes — to the Jump For Charity, where riders are paired with different local charities, competing for prize money on their behalf.

All of this would not be possible without the sponsors, a total of 90 with a wide range of businesses eager to interact with this highly desirable demographic. For Kay Lawson, a real estate agent with Douglas Elliman, the Hampton Classic is the perfect combination of business and pleasure.

Lawson is an equestrian herself who competes in the Adult Amateur Jumping series at 1.15 meters. Her horse, Bombadella, is her trusted partner-in-crime.

“I have a very competitive horse, and if I make a mistake, she can usually cover it up for me,” admitted Lawson with a laugh. With Douglas Elliman as a major sponsor, the Hampton Classic is not just a place to compete but a networking haven, whether it’s in the saddle or in the VIP tent.

“It’s fun to be here,” said Lawson. “I see clients and friends and there are a lot of social things happening. Elliman is such a huge sponsor and our president, Scott Durkin, is a dressage rider.” For those unfamiliar, dressage is a discipline on the flat where horses are almost like ballet dancers performing to choregraphed music. “His presence solidifies the company’s support of the horse community,” she added.

From Humble Beginnings

This is the 43rd Hampton Classic Horse Show, which had its humble beginnings in 1971 as the Southampton Horse Show at the Topping Riding Club in Sagaponack. Back then, it was a DYI project where riders would polish their tack, braid their ponies’ manes (mine was Aphrodite), and earn the best reward, an Italian ice.

Now, the Classic is one of the largest horse shows in the country and has the proud status of a United States Equestrian Federation Heritage Competition, a prestigious title conveyed on certain shows over 25 years old that have provided for their communities, as well as the horse community as a whole, in an unprecedented fashion.

Aside from world-class equestrian competition, the Hampton Classic is the pinnacle of the summer social season with leaders in business, fashion, finance, and entertainment turning out to enjoy. You may see Christie Brinkley, Sarah Jessica Parker, Jennifer Lopez, Jerry Seinfeld, Sofia Vergara, Billy Joel, or Mary Kate Olsen.

Spectators can see all levels of competition from the Lead Line class with adorable toddlers and ponies to Olympic champions competing in the $300,000 Hampton Classic Grand Prix presented by Douglas Elliman, which takes place on Sunday, September 2. While the well-turned-out riders and horses may look similar, there are many different divisions and categories for all age and skill levels, including the finals of the Long Island Horse Show Series for riders with disabilities. The show also includes a chic boutique garden, petting zoo, international food court, a champagne bar, and luxury cars and boats on display.

It is the only time men and women compete directly. The winner of the FEI World Cup Jumping title is a woman, Beezie Madden, who is at the top of her game, at 54, and is competing here this week. What other sport would see women in their 50s and even 60s excelling at the top level? It is this longevity that also attracts women amateurs, like Kay Lawson, to the sport.

Lawson points out that in both real estate and equestrian sport, women have traditionally been dominant leaders. She commented, “Because of the history of show jumping, you’ve had women Olympians for so long it’s part of the fabric of the sport. Like real estate, a lot of the top brokers are women, and it’s historically been that way and no one is surprised at that. That perception in other industries is shifting which is great.”

Real Estate Plus Riding

Lawson grew up around the corner from her current barn, Twin Oak Stables in Bridgehampton, where she now trains with the successful Grand Prix rider from Ireland, Jonathan Corrigan. “I begged my parents to ride, and at seven, they finally let me,” said Lawson, “And it was hopeless after that.”

Lawson got back into riding after college and law school when she bought her first horse, an off-the-track thoroughbred which she trained to compete as a hunter. Her dedication was unwavering as she would rise early to ride before heading into her law firm. But a perfect solution to balance her passions arrived in the form of real estate.

“Real estate plus riding is a great marriage,” she reported, with her specialty in equestrian real estate. “Working with riders and their families is one of my favorite things to do because it’s so specialized and I’m so close to that community. Because I ride, I understand barns, locations, footing, fencing, stalls, and all those details. I can also service my clients in Wellington, FL at the Winter Equestrian Festival, where I compete. But the process and journey of finding a house for anyone, equestrian or not, is always exciting.” Lawson recently sold a dressage barn, but to a non-equestrian family who just loved the land.

When asked how she sees the state of the Hamptons real estate market, Lawson responded, “My dad was a broker here with an office next to Candy Kitchen in Bridgehampton. He always said this is two hours from Manhattan with the most beautiful beaches and views and main streets, and it’s always going to be a place people want to be.”

Sag Harbor is home for Lawson but her barn also functions as her adjunct home. She said, “My family is my dog and my horse and my barn and my friends.” The barn can be a haven for all sorts, including a top oncologist from Sloan Kettering who rides with Lawson. “Riding is her favorite thing,” Lawson said. “She just loves horses and connecting with everyone at the barn. That’s why it’s so special.”

Lawson also pointed out how the horse world gives back to the broader community, like the recent fundraiser she attended for the Center For Therapeutic Riding on the East End, which services special needs children and adults at their riding program out of Wölffer Estate Stables in Sagaponack.

Lawson wanted to relay an important message about riding. “It’s more of an accessible sport than the perception,” she said. “I had a lot of opportunity growing up but I never owned a horse until I bought it myself, and I’ve done this myself for the last 15 years. It’s the real estate that enables me to do this and I feel so fortunate. I have the contacts and connections now because I’m part of the community.”

So, for all the parents out there, that first pony ride at the Hampton Classic might just lead to a lifelong passion.

To contact Kay Lawson, call 631-725-0200 or email