Middleburg, Virginia, Has Been Quietly Hosting Old Money Since the Kennedys Rented a Farmhouse There

Middleburg, Virginia, was founded in 1787 by Colonel Leven Powell as a stop midway along the Ashby Gap trading route between Alexandria and Winchester, which is how it got its name. It has spent the two and a half centuries since becoming the unofficial capital of Virginia's hunt country, a low-key equestrian enclave that has drawn old money without ever really marketing itself.

A hunting rivalry that put it on the map

Virginia's hunt country became a genuine centre of American equestrian sport after a celebrated 1905 competition near Middleburg pitting American-bred foxhounds against English imports. The result cemented the area's reputation, and the Middleburg Hunt has run continuously through the surrounding countryside since.

The Kennedys' weekend escape

Jacqueline Kennedy first knew Middleburg from childhood horse shows at her stepfather Hugh D. Auchincloss's nearby estate, Merrywood. After John F. Kennedy's election in 1960, the couple leased Glen-Ora, a farm with its own stables barely a mile from the village centre, and used it for weekends away from Washington. They later bought 39 acres nearby and began building their own house, Wexford, cementing Middleburg's status as the President's retreat of choice.

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Mellons, Harrimans and the Master of Foxhounds

The philanthropist Paul Mellon and his wife, the botanist and garden designer Bunny Mellon, were fixtures of the Middleburg Hunt, as was Pamela Harriman, all of whom at various points served as the hunt's governors. Bunny Mellon was a close friend of Jacqueline Kennedy's and a regular host during her Middleburg weekends, part of a wider circle that also included members of the du Pont and Firestone families.

What it isn't

Middleburg has none of the beachfront glamour of the Hamptons or the ski-town polish of Aspen. It's a village of a few thousand people built around horses, hounds and a handful of old inns, and the old money that gathers there tends to prefer it stay exactly that unremarkable.

Traveller tips

• Middleburg is about an hour's drive from Washington, D.C., with no direct rail service.
• The Red Fox Inn, dating to the 18th century, remains one of the village's oldest continuously operating establishments.
• Fall and spring bring the area's main steeplechase and point-to-point race meetings, when the village is at its busiest.
• Several wineries operate in the surrounding Loudoun County countryside, a newer addition to the area's old hunt-country economy.