By Britney Grover

Though horse showing in Gulfport, Mississippi, may be off the beaten path for some, it’s a cherished annual tradition for others. Coastally located on the Gulf of Mexico, Gulfport has been home to the Gulf Coast Winter Classics for 20 years, with classes from lead line to grand prix and now over $1,000,000 in prize money. Cheryl Rubenstein visited the show at Gulfport in one of its inaugural years after a 20-year hiatus from riding, and has been showing there every year since 2002.

In her youth, Cheryl rode ponies and through juniors to one year as an amateur owner. Then she lost two horses in a row. “I stopped showing for school and a career until my husband asked if I wanted a horse again. He clearly had no idea what that really meant,” Cheryl said. “I’ve been showing again now for 15 years.”

Cheryl was a corporate finance and investment banker, but now fills her time with volunteer work — including being on the board of directors and executive committee of the USHJA, the board of the USHJA Foundation, and the National Breeds and Disciplines Counsel and Awards Committee for US Equestrian. “So, in other words, I was an income-producing asset and now I am an expense and a liability on our personal financial statement,” she joked.

Cheryl knows the South. She lives in Houston, Texas, but rides out of Memphis, Tennessee, with Phoebe Sheets, “who has been a friend and my trainer for more years than either one of us would like to admit,” Cheryl said. Her time-tested showing relationship with Phoebe regularly pays off in the adult amateur hunters 50+, including during her annual trip to Gulfport.

The Gulfport experience is what you make of it — from nightlife, big-name performances and numerous parades at Mardi Gras to simple ocean views and quiet hotels. “If luxury, spas, gambling and shows are the preference, I would recommend a casino hotel,” said Cheryl. Gulfport and nearby Biloxi host many large casino resorts with fine dining, all-night gaming and well-known performers.

“However,” Cheryl continued, “if proximity to the horse show due to an early wake-up call is one’s priority, I would look for a hotel closer to Highway 49.” Located just north of Gulfport’s action, the Gulf Coast Winter Classics are held at Harrison County Fairgrounds, within 15 minutes of highly-rated chain hotels.

When not at the horse show, Gulfport offers something for everyone, from golf, beaches and hiking to museums, gambling and shopping. “There are attractions like the Center for Marine Education & Research, breweries, and the Stennis Space Center,” said Cheryl, “but what I think most attracts people is the proximity of nice casinos with known entertainers. The Beau Rivage, part of the MGM network, has a piece of the skyline and clearly attracts top entertainment.”

At the Center for Marine Education & Research, guests can explore a museum as well as see ocean life like stingrays, sharks, fish and even dolphins. Take a tour of NASA’s Stennis Space Center from its visitors’ center and museum, the INFINITY Science Center, where the entire family can also enjoy hands-on learning experiences. Shopping can be one-stop at the Gulfport Premium Outlets, featuring Polo Ralph Lauren, Under Armor, Lacoste, Sunglass Hut and more. With so many top performance venues, checking the calendars might seem daunting — but makes it easy to check all upcoming events at once, and to plan your entire trip at once.

With time for a relaxing cocktail, Cheryl recommends anyplace with a waterfront view. “Chimneys or Salute, but I’m not the best person to ask because I’m going for the food — I’ll take a drink, but I want the food!” Cheryl admitted. No matter how you fill your itinerary, Gulfport has dining options for every palate. If you don’t leave the show grounds for lunch, as Cheryl admits, food vendors offer a variety of salads, burgers, smoothies and more. But dinner away from the fairgrounds is really something to look forward to.

“I really enjoy Chimneys for a good meal, good service, a relaxing ambiance and a place I can actually talk to others I’m with,” said Cheryl. At Chimneys, experience an upscale plantation home-style meal either indoors or on the wrap-around porch. Classic Southern and seafood are sure to make your mouth water, with menu options such as Cheryl’s personal favorite, Oysters Chimneys: oysters baked in a house version of creamy Bienville sauce with shrimp, mushrooms and onions, with fresh-baked bread, house salad and your choice of side.

Speaking of oysters, Cheryl also enjoys Half Shell Oyster House for oysters or traditional gumbo in a French Quarter-inspired setting. “Koi has never let us down,” she said of Koi Sushi, an authentic sushi restaurant conveniently located nearer to the horse show along Highway 49. Visitors and locals alike take seats at the entertaining hibachi bar, or at a more peaceful table to enjoy teriyaki, tempura and other classic Japanese flavors. And don’t worry if you’re headed straight from the barn. “Koi has been gracious to let us in when we have been our dirtiest from the horse show,” Cheryl said.

While Gulfport has much to offer, the Gulf Coast Winter Classic shows may still be the highlight of your trip. The series emphasizes the adage that all of Gulfport seems to echo: something for everyone. When asked what makes showing at the Gulf Coast Winter Classics special, Cheryl was quick to respond. “Easy! Good management, exhibitor-friendly decisions, kind office staff and multiple options for showing whether the horse or rider is inexperienced, needs to build confidence or wants a high-performance opportunity,” she said. “Anytime I have had a wish, a request or a concern, all I have ever had to do is say ‘knock, knock.’” As Cheryl said, the door to the Gulf Coast Winter Classics — and Gulfport — is always open.

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