A 45-mile drive west on U.S. Route 50 brings you to Middleburg, a nook in Virginia’s horse country that boasts vineyards, shops and hiking trails enjoyed by locals and Washingtonians looking for a one-day getaway.
Notable escapee first lady Jacqueline Kennedy kept horses on a Kennedy family farm in Middleburg during her years in the White House, and her jaunts to the quaint little town often stirred frustration among White House staff counting on the first lady to appear at ribbon-cuttings and official lunches. The equestrian first lady, however, often preferred fox hunting.
The equestrian scene is still very much a part of Middleburg’s appeal. The annual fall race has attracted presidents and lures more than 7,000 patrons every year.
Restaurants bear names like the French Hound, in an ode to the town’s sport of fox hunting, and oil paintings of horse stables and green pastures appear even in the ice cream shops.
One of the more famous restaurants in town is the Red Fox Inn, which is a collection of small cottages for overnight stays anchored by a cozy dining spot that serves warm quiche for brunch and small game for dinner. Kennedy once stayed at the inn, which still proudly displays her thank you note along with — of course — an equestrian display.
The inn sits on Washington Street, the main drag through Middleburg’s downtown where visitors can peruse boutiques and gourmet food and gift shops (a recent visit to the Christmas Sleigh yielded no sighting of shop owner and famous former Clinton staffer Linda Tripp).
Closer to Middleburg off Route 50, small wooden signs noting local wineries pop up like pleasant billboards. Tourist groups, bridal showers and weekend warriors pour into the various wine watering holes for tastes that are usually priced at $10 to $15.
Swedenburg Winery and Valley View Farm, owned by a transplanted Midwestern couple and just off U.S. Route 50 a mile from downtown Middleburg, has a pleasant staff and gorgeous views of the Blue Ridge Mountains. The working farm also raises Black Angus cows, which greet you as you drive into the estate.
Chrysalis Vineyards, just outside Middleburg, has garnered a following among Virginia wine enthusiasts for its Sarah’s Patio white wine and its wine cellar tour.
Seasonal activities like apple picking in the fall or hunting down the perfect freshly cut Christmas tree in the winter are equally popular.
Middleburg was established in 1787 on a 50-acre parcel of land as the halfway — or “middle— — spot between Alexandria and Winchester in the Shenandoah Valley. Alexandria, of course, is now an extension of Washington, Winchester is the county seat of Frederick County, and Middleburg is somewhere in between with beautiful scenery enjoyed by wine drinkers and hikers.
At just an hour’s drive away, the little historic town makes for a pleasant Saturday jaunt.