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Horses, Hats, and Summer Fun at Hampton Classic

Thu, 08/27/2026 - 10:29
At the Hampton Classic’s opening day Sunday, Olivia Smart, riding Prada from Wolffer Estate Stables, competed in the leadline division, and also (not related) lost a tooth that morning.
Durell Godfrey

“The horses, the sport, the community, the summer day, the shopping — it’s so much fun.”

In one sentence, Erica Velasquez summed up the magic of the Hampton Classic, which spurred into action on Sunday in Bridgehampton. The weeklong event, now in its 51st year, typically runs through Labor Day weekend, but falls a week earlier on the calendar this summer, wrapping up on August 30. Velasquez, an Amagansett native and owner of EvolveEast Yoga, has been coming to the Classic for at least a decade. This year, she set up her V.I.P. table on opening day in the pouring rain.

At left, Adleigh Callahan, right, competed in her first show Sunday, riding Oopsie-Daisy and finishing a section champion in the 2-to-4-year-old leadline group. At left, Emilia Dolan gave the pony Batteries Not Included, a heartfelt hug.  Durell Godfrey

“It was tough to set up our table, but once the rain stopped we were fine,” she said, pointing out their glassware and flowers from Osborn Girls Flower Stand in Wainscott, wine from Wolffer — of course — and Jamagansett pop tarts.

The morning storm put the show on hold for about 30 minutes, but long before noon the children’s leadline competition was in full swing, with precious pony riders, ages 2 to 7, parading around the Grand Prix ring.

Danielle and Carolyn Upward of Brookville in the V.I.P. tent on opening day. Carolyn won a third-place ribbon in her first-ever walk-trot, riding Qantar’s Chico, on Monday. Alison Morris Roslyn

Carolyn Upward of Brookville was one of those young riders just a year ago, and a section winner of the 5 to 7 leadline class, on her pony, Twilight’s Whisper. On Monday, she won a third-place ribbon in her first-ever walk-trot, riding Qantar’s Chico.

“He’s a bay pony. He has a black mane and tail and he has a brown body,” she said. The two have been riding together, three days a week since the winter, adding a training day this summer, which clearly paid off. “I learned how to canter a little bit.”

“We’re really proud,” said her mother, Danielle Upward.

The Hasson family from Brooklyn poses with their purchases in front of the Aspinall Ring. This was their first visit to the Hampton Classic. They are, from left, David, Hanna, Albert, and Aida. Alison Morris Roslyn

Over by the Aspinall Ring, Albert Hasson, his wife, Hana, and their children David and Aida had traveled from Brooklyn to enjoy their first Hampton Classic. 

“Just a fun great day — beautiful weather, nice outing,” he said. “A little shopping, a little eating, watching the horses perform. It’s a great way to end the summer, being at a horse show.”

Tommy Pickles was one of their favorites — available on a stick, as a flight of four flavors, or cut into chips and served in a bowl. Thomas Grimes of Massapequa makes them from scratch with seasonings like Cajun dill, horseradish, and pineapple jalapeno. If it sounds inelegant to eat pickles on a stick at a horse show, nearly everyone parked on the picnic tables across from the Land Rover tent and Hermès boutique was chomping on one.

Jennifer Parker, a celebrity chef, Tammy Gatto, a real estate agent with Signature Premier Properties, Maggie Delany, co-founder of the Entrepreneurs and Professionals Network, and Carina Tom, owner of V&P Events, were in the V.I.P. tent on opening day. Alison Morris Roslyn

Marders had its usual sparkling array of colorful hats on display this year — with bugs and butterflies a prominent theme. Just a few boutique stalls away, Min Santandrea, the founder of SantM, was selling slightly more scandalous attire.

“They’re Furlane. They’re traditional Venetian shoes that were originally made about 250 years ago for the Venetian upper class as their house shoes. However, the Venetian royalty discovered they could sneak out in the middle of the night to meet their lovers in their house shoes and ever since, it’s been a status symbol to wear them outside because it means you’re of the royal blood and you have lovers,” she said. “I call them the Italian version of “The Scarlet Letter,” which is a lot more fun and forgiving than the American version.”

On Tuesday, Irene Neuwirth and Gucci Westman crowned DandyLion Designs the winner of the boutique contest. Founded by Ashley Farland in Vermont three years ago, DandyLion features home goods, handcrafted in Vermont.

Over in stable row, Wolffer Estate had a brand-new ribbon to display, thanks to Joey Wolffer and Rockstar’s 10th place finish in the $30,000 Jumper Challenge, which raised $4,500 for the Kevin Babington Foundation. Mr. Babington, an Irish Olympian, was paralyzed from the neck down when he fell from his horse during the Grand Prix at the Hampton Classic in 2019. His foundation provides funding and support for equestrians who sustain spinal injuries.

On opening day of the Hampton Classic Sunday, Troy Powell, the head horse show secretary, in white at center, was given the inaugural Jean Lindgren Memorial Trophy named for the show’s longtime co-executive director, who died this spring. Along with the staffers on hand were Ms. Lindgren’s son Baylis Greene, second from left, his daughters, Bennett and Penelope, and his wife, Julie.  Durell Godfrey

The inaugural Jean Lindgren Memorial Trophy was also presented to the Hampton Classic’s Troy Powell, the head secretary of the horse show. Lindgren, a Sagaponack resident and one of the original co-executive directors of the Hampton Classic, died in May at 85 years old. Each year, the award in her name will go to a member of the Classic staff who demonstrates outstanding dedication and behind-the-scenes service.

Horses participating in Monday’s Animal Adoption and Welfare Day — some adorably small — were also on hand Sunday. At left, Valerie Angeli of RedHorseStar Productions, who organized the event, and Kelly Stackpole of Rising Starr Horse Rescue in Connecticut, introduced Gerkin, Cucumber, and Graham Cracker. Durell Godfrey

Animal Adoption Day was Monday, with horses, dogs, and cats on display. Admission and parking were free that day. Georgina Bloomberg, a rider, owner of the New York Empire equestrian team and daughter of former New York City mayor Michael Bloomberg, sponsored the event, welcoming spectators to the Aspinall Ring to learn more about rescue horses and animal welfare.

“This is the most important day. The Hampton Classic has been so meaningful to me growing up,” Bloomberg said in a press release. “I know how lucky I am to have horses to compete here, and it’s our way of giving back and educating on how one can help.”

There is plenty of fun to come this weekend. Saturday is Kids Day, featuring pony rides, dance parties, circus performers, face painting, and more.

Sunday is the mane — ahem, main — event: the $400,000 Longines Hampton Classic Grand Prix is scheduled for 3 p.m. Jessica Mendoza of Great Britain won the title last year and will return to defend it. Her toughest competition will likely be the current world number one, Kent Farrington of the United States, who won the event in 2012 and 2013.

Expect elaborate V.I.P. tables, extraordinary hats, big crowds, and traffic backups, especially on Sunday.

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