Each summer, the Hampton Classic Horse Show brings together Olympic medalists, national champions, youth amateurs and droves of “horse people” — from celebrities to local fans — for a week long show of jumping, celebrating horses and the equestrians who ride them. Along the way, there’s shopping, food trucks, plenty of glass-clinking and even horse (and dog and cat) adoptions.
However, at some Hamptons stables and ranches, horses take center stage 52 weeks of the year. They offer a variety of ways to bond with our equine friends, from horseback riding experiences ideal for an off-the-beaten-path date to camps and riding lessons for one-day Hamptons Classic hopefuls. There are also chances to learn about proper horse care. From a ranch at The End that throws a horseshoe at the expected beginnings of the American Cowboy to stables that prove it’s never too late to learn to ride, these are the best to horse around in the Hamptons.
Deep Hallow Ranch, 1929 Montauk Highway, Montauk, 631-668-2744
Deep Hallow Ranch isn’t in Texas or the Wild West, but it’s hailed as the oldest cattle ranch in the U.S. and the birthplace of the American Cowboy. Take that, Yellowstone. Now helmed by Patrick and Cate Keough — who met on the ranch — Deep Hallow offers family-friendly fun. Children 5 and under can experience their first pony ride, and children aged 6 and 7 can progress to shorter trail rides. People 8 and up can take a beach ride — a unique way to explore Long Island’s shores. There are also trail rides as well as private experiences ideal for intimate date day trips.

Stony Hill Stables, 268 Town Lane, Amagansett, 631-267-3203
Founded by Liz Hotchkiss more than six decades ago, Stony Hill Stables holds the distinction of being home to one of the Hamptons’ longest-running stables. Liz passed the baton to her daughter, Wick, and Stony Hill Stables continues to offer horse experiences to people of all ages. Riders as young as four can begin taking lessons, and adults are welcome to get back on the horse and learn (or get on one for the first time), too. Stony Hill’s instructors focus on dressage, hunter/jumper and equitation — if competition is your goal. A summer camp caters to both beginners and more advanced youth riders.
Sea-Aire, Inc., 2 Uncle Leos Lane, Water Mill
This show stable houses horses on Water Mill’s Pinnacle Farm from April through November. The horses winter in Florida. The trainers specialize in preparing horses and riders for competitions in a supportive environment. The facility meets the mission — indoor and outdoor arenas allow training to happen, regardless of Mother Nature’s mood. A Grand Prix Field with an Irish bank, liver pool, table bank and open water allows riders and horses to become comfortable with various obstacles, making them competition-confident.

Wölffer Estate Stables, 41 Narrow Lane East, Sagaponack, 631-537-2879
Found on 100+ acres of land, Wölffer Estate’s Stables include more than 80 stalls, 39 individual paddocks, an Olympic-sized dressage ring and a Grand Prix field with natural and traditional jumps. Indeed, it’s come a long way since the day Christian Wölffer purchased it — then, it was a farmhouse with some barns. The riding school is geared toward preparing students for competition and caring for the horses (heat lamps keep them cozy when temperatures dip). Trainer and barn manager Ben Tula competed internationally before pivoting to teaching.
Gray Horse Farm Hamptons, 849 Hayground Road, Bridgehampton, 203-910-6297
This 115-acre farm, featuring three outdoor and two indoor rings, is the culmination of a decades-long journey that has involved risk, tragedy and — ultimately — a triumph for founder Tracy Broxmeyer, rooted in her love for both her human and equine family members. Broxmeyer left her marketing career to open the farm in 2001, restoring a historic brick barn from a bygone era. When her husband, Mark, was diagnosed with and later died from pancreatic cancer, Broxmeyer ultimately chose to open a “Pony Palace.” Today, Erin Stewart, who called horse expert Don Stewart “Dad,” leads the training team’s efforts to foster a lifelong love of riding. A pony camp is also available each summer.
Topping Riding Club, 58 Daniel’s Lane, Sagaponack, 631-537-0948
Situated on 25 acres not far from the village of Bridgehampton and the Atlantic Ocean, Topping Riding Club offers a pony camp, lessons and a pair of horse shows each year. Members (but not the general public) are also able to take beach rides. Fun events — like a Halloween costume contest for humans and horses alike — also keep the good times rolling (or riding, if you will) at the club.

Amaryllis Farm Equine Rescue, 864 Lumber Lane, Bridgehampton, 631-537-7335
This horse farm and rescue began in 2005 in honor of Christine Barrett-Distefano’s first horse, Ben. One rescue, Amaris, inspired the formation of the Sanctuary for Seniors and Special Needs Horses four years later in 2009. Today, you’ll find resident horses in their late teens through their mid-30s, including equine friends saved from slaughter lots and who survived car accidents. From May 1 through October 1, guests can take an hour-long tour of the 10-acre sanctuary and learn more about the horses, their needs, and what brought them there. A $250 donation is required for two adults (with additional adults costing $50). Children can take the tour for free. You can also sponsor minis, horses and ponies for $10+, which helps fund blankets, emergency care and more.
Silver Tide Stables, 41 Narrow Lane East, Sagaponack, 917-903-6141
Silver Tide Stables offers private lessons for riders of all ages with grand Grand Prix goals and those simply looking to have fun. Indoor and outdoor rings allow for all-weather lessons. A daily pony camp each summer teaches young riders about grooming, mounting and the importance of building a trusting relationship with a horse from the jump.