Leesburg
Founded in 1758, Leesburg is the largest town in the Hunt Country and a good base for exploring the region. Although not as picturesque as Middleburg, it has considerable charm, with architecture ranging from pre-Revolutionary to late 19th century. The center of Leesburg and its historic district is at the intersection of Market Street (Va. 7 Business) and King Street (U.S. 15 Business), where you'll find the brick Loudoun County Court House, built in 1895, which contains a mix of Roman Revival and classical elements. Most of what you will want to see is within 2 blocks of this key crossroads, including one of the largest collections of antiques dealers in Virginia.
Getting Around Leesburg -- The free Leesburg Town Service Trolley (tel. 877/777-2708 or 540/338-1620; www.transitservices.org) runs between the Loudoun County Government Center, on Harrison Street in downtown Leesburg, and the Leesburg Corner Premium Outlets via Market Street (Va. 7 Business) daily every 30 minutes from 7am until 6pm. It passes the Leesburg Visitor Center on Catoctin Circle.
Middleburg
One of Virginia's most charming small towns, Middleburg is home to those who can afford to indulge in horses, horse breeding, steeplechase racing, and fox hunting. I am not kidding; you will see jodhpurs and riding boots worn here, although locals claim that only "Paddock Princesses" -- who seldom ride but who like to look the part -- actually wear the gear in town. Whoever's wearing it, this village is so unusual that the weekly rag calls itself the Middleburg Eccentric. In addition to real estate notices for farms selling for multi-millions, the paper carries ads for firms offering horse clipping and mane pulling. Keep an eye peeled because in addition to being very, very wealthy, the person walking next to you could be very, very famous, too.
Even if I do turn into a chicken when I get near a horse, I thoroughly enjoy pretending I'm filthy rich while strolling Middleburg's shady brick sidewalks -- in a polo shirt and khaki trousers, quite appropriate attire here. I like poking my head into high-end shops with names like Crème de la Crème that sell "home embellishments," stopping for a cone at Scruffy's Ice Cream Parlor, and grabbing a shot of caffeine at Cuppa Giddyup. If I'm lucky, Books & Crannies is popping champagne corks to honor a local author's new work.
Middleburg is included on the National Register of Historic Villages, and with 600 residents, it's about the same size today as when it was settled in 1731. You can't get lost here, for the village occupies just 6 blocks along Washington Street (U.S. 50), with just two streets -- Federal and Marshall -- running parallel on either side. Start your tour at the Pink Box Visitor Information Center, on Madison Street a block north of the one traffic signal on Washington Street. The public pavilion next door is dedicated to the late Jacqueline Kennedy Onassis, in honor of the contributions she made "during her happy years in the village."
