The Highlands Cup Horse Show, held from October 8–12 at Keane Stud in Amenia, New York, offers five days of elite show-jumping competition, highlighted by the Major League Show Jumping team event on Friday and the $340,000 Highlands Cup CSI5 Grand Prix on Saturday. This event follows the successful second annual Silo Ridge Masters (October 1–5), creating a 10-day equestrian and cultural celebration in the Hudson Valley.

In addition to world-class horse shows, attendees can experience the Bridlemont Concours at Highlands on October 12, featuring over 30 rare cars and motorcycles. The event also includes live music performances by Third Eye Blind with Dinosaur Jr. on October 10, and LeAnn Rimes with Brothers Osborne on October 11, alongside five-star dining, shopping pop-ups, and special events, making the Highlands Cup a premier destination experience.