Highlands Cup Horse Show Brings World-Class Jumping to the Hudson Valley

The October event in Amenia, New York, united elite equestrian competition, luxury automobiles, art, gourmet dining and philanthropy against the scenic backdrop of the Highlands and Silo Ridge.

October 19, 2026
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The Highlands Cup Horse Show was a totally world-class event. Held over two glorious October weekends, it featured the best horse show jumpers on earth as well as a display of exclusive automobiles, art exhibitions, gourmet hospitality, exclusive boutiques, the Autumn Invitational Discovery Land Co., Masters Highlands Cup and Bridlemont Concours. Collectors, competitors and guests from across the country gathered in Amenia, NY, just across the border from Connecticut and adjacent to Silo Ridge.

Spectators on the hillside and in the exclusive Legacy Club watched world-class jumpers compete for a $340,000 grand prize. Browsers voted for favorites among meticulously preserved classic automobiles. Children jumped in a bouncy castle, guests listened to tennis great Ilie Nastase and other illustrious panelists, and generous patrons bid on art in an Evening of Giving auction benefitting charities Angels Road to the Top. Everyone dined on delicious cuisine, from classic favorites cooked in the haybale decorated Concession Stand to the gourmet fare served in the luxurious lounge spaces of the Legacy Club, its hospitality experience created and curated by architect and designer Andrew Franz.

Showcasing the vision of CEO and Founder Pedro Torres, the 1000 acre Highlands Hudson Valley site and neighboring Silo Ridge are emerging as a summertime alternative to Wellington, FL. These premier community settings allow horse lovers and families to flourish in privacy amid stunning landscapes, top sports and modern luxury.

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