Photo by Howard Allen

Photo by Middleburg Photographer Howard Allen

Jackie Kennedy’s style and grace epitomized Loudoun County’s horse country and its capital, Middleburg. Today marks the 16th anniversary of her death, so in memoriam, I thought I’d share a little bit about her time in Loudoun, a place she visited on and off for nearly 40 years.

In the early 1960s, President John F. Kennedy and his family used Middleburg as a retreat from the pressures of the presidency. The Kennedys leased a 400 acre 19th century farm, Glen-Ora, to relax, foxhunt, and socialize with friends. Later, they built their own weekend country retreat, “Wexford,” on 39 acres in Middleburg which they purchased for $26,000 from a local farmer. JFK even held rare press conferences in the Jeb Stuart Room at The Red Fox Inn in town.

Jackie was a favorite with local residents, and while in Middleburg she treasured “normal” time with her children, John Jr. and Caroline, reading bedtime stories, shopping, and teaching them to ride their ponies. JFK, also a regular visitor, would fly in by helicopter to attend Sunday mass at the Middleburg Community Center. Local photographer Howard Allen captured Jackie and the kids riding – the photo shown here became their official 1962 birthday portrait and made the cover of Life Magazine. On the day that photograph was taken, he recalled witnessing a group of men (including JFK) quickly exiting the house and loading into a waiting helicopter, followed by someone running out of the house waving a briefcase. Allen laughed as he described the quick grab that was made by an outstretched hand, just before the helicopter took off, “just like a businessman whose wife hurries after him with his forgotten briefcase!”

In the 1990s, Jackie Kennedy Onassis often returned to spend foxhunting weekends in the Middleburg countryside, which was filled with happy memories from her time as First Lady. She stayed at The Red Fox Inn’s McConnell House, not far from Wexford. On your way into the Inn’s restaurant, look for the handwritten letter from Jackie preserved below the glass on the counter. Today, the public pavilion and garden next to Middleburg’s “The Pink Box” Visitor Information Center are dedicated to Jackie in honor of the contributions she made to the town during her residence. Also, don't miss the chance to pick up a “Cow Puddle” cookie at the Upper Crust Bakery. It’s “a local take on a gooey toffee-ish cookie,” according to The Washington Post. Reportedly, they were Jackie’s favorite. They’ll be on your list of favorites, soon, too!