Highlands Cup Horse Show at Keane Stud in Amenia

The Highlands Cup Horse Show features three action-packed days (Oct. 9–11, 2026) of elite show-jumping, including the fan-favorite Major League Show Jumping team competition on Saturday and the $340,000 Highlands Cup CSI5 Grand Prix on Sunday.

This event is the second of two major equestrian competitions running back-to-back at Keane Stud. The Discovery Land Company Masters is set for Oct. 2–4, 2026, making Amenia the place to be for two straight weekends of sport and culture!

Along with the horse shows, you'll enjoy the Bridlemont Concours at Highlands, a world-class showcasing of more than 30 rare and iconic cars and motorcycles, set for Oct. 11, 2026.