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 Courthouse, 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.

Exploring Leesburg -- The free Leesburg Town Service Trolley (tel. 877/77-2708 or 703/777-2420; www.vatransit.org) runs between the Loudoun County Government Center (on Harrison St. in downtown Leesburg) and the Leesburg Corner Premium Outlets via Market Street (Va. 7 Business) every 30 minutes Monday to Friday from 7am until 6:30pm, Saturday from 10am to 9pm, Sunday noon to 6pm. It passes the Leesburg Visitor Center.

Waterford Village

A favorite Sunday drive for us northern Virginians is to the enchanting hamlet of Waterford, with so many 18th- and 19th-century buildings that the whole village is a National Historic Landmark. Surrounded by a rolling landscape of 1,420 acres, it offers vistas of farmland and pasture that unfold behind barns and churches. You'll feel as though you've entered an English country scene. A Quaker from Pennsylvania, Amos Janney, built a mill here in the 1740s. Other Quakers followed, and by 1840, most of the buildings now on Main Street and Second Street were in place. In 1870, the railroad bypassed Waterford, and because the pace of change slowed, much of the town was preserved. Affluent professionals who work in Washington, D.C., and the bustling northern Virginia suburbs now own many of the homes. In other words, it's a real town, not a theme park like Williamsburg, so please don't traipse through their front yards.

Usually counted in the few hundreds, the population swells to the many thousands on the first full weekend in October, when local residents stage the annual Waterford Homes Tours and Crafts Exhibit, one of the region's best. Concerts and other events are held here throughout the year.

Be sure to get a walking-tour guide booklet at the Leesburg Visitor Center or from The Waterford Foundation, Inc., P.O. Box 142, Waterford, VA 20197 (tel. 540/882-3018; fax 540/882-3921; www.waterfordva.org). The foundation's office is in the Corner Store at Main and Second streets and is open Monday to Friday 9am to 5pm. Ask the foundation about walking tours, which are given on some Sundays.

Waterford is about 6 miles northwest of Leesburg. Don't take Old Waterford Road; it's not paved. Instead, follow Va. 7 west, turn right onto Va. 9, then right on Clark's Gap Road (C.R. 662) into Waterford.

On the Loudoun Wine Trail

Loudoun County has several vineyards worth visiting. Be sure to pick up a free copy of "Touring Guide to DC's Wine Country" at the Leesburg Visitor Center. It has a map and describes each winery's specialty, location, and business hours.

Rather than risk a DUI charge, you can join Reston Limousine (tel. 800/LIMO-141 [546-6141] or 703/478-0500; www.restonlimo.com) on one of its all-day weekend tours to four local wineries. They cost $35 per person. Reservations are required by 5pm Thursday prior to a Saturday or Sunday tour.

Virginia Wine Adventures LLC (tel. 877/VA-GRAPE [824-7273]; www.vawineadventures.com) also will tailor a tour to your specifications.

Driving myself, I would start at Tarara Vineyard & Winery, 13648 Tarara Lane (tel. 703/771-7100; www.tarara.com), overlooking the Potomac River, where wines are aged in a 6,000-square-foot cave. Their 2002 viognier won the Virginia Governor's Cup gold medal, not that they will have any left for you to taste. It's open daily 11am to 5pm, to 6pm on weekends from June through December. Tours and tastings run continuously. From Leesburg, drive north on U.S. 15 to Lucketts, then east on C.R. 662.

Near Tarara and the river on Spinks Road is Lost Creek Winery (tel. 703/443-9836; www.lostcreekwinery.com). It's open Thursday to Monday from 11am to 5pm.

Northwest of Leesburg are Loudoun Valley Vineyards, on Va. 9 (tel. 540/882-3375; www.loudounvalleyvineyards.com), which has tours April to December Saturday and Sunday from 11am to 5pm; and Breaux Vineyards, north of Hillsboro on C.R. 671 (tel. 800/492-9961 or 540/668-6299; www.breauxvineyards.com), whose Mediterranean-style tasting room is open daily from 11am to 5pm. On C.R. 690 is Doukénie Winery (tel. 540/688-6464; www.doukeniewinery.com), which is open daily from noon to 6pm.

In the southern part of the county near Middleburg, the most interesting of the local wineries is Piedmont Vineyards, on Halfway Road (C.R. 626) about 3 miles south of town (tel. 540/687-5528; www.piedmontwines.com), a former dairy farm whose barn now houses a tasting room and gift shop. The tasting room is open daily 11am to 6pm.

Off U.S. 50 a mile east of the village, Swedenburg Estate Vineyard, 23595 Winery Lane (tel. 540/687-5219; www.swedenburgwines.com), occupies part of Valley View Farm, founded about 1762. We can thank the late Juanita Swedenburg for bringing the lawsuit in which the U.S. Supreme Court ruled that interstate wine sales over the Internet are okay. It's open Saturday and Sunday 11am to 5pm, weekdays by appointment. Farther east on Champe Ford Road (C.R. 629), between Middleburg and Aldie, is Chrysalis Vineyards (tel. 800/235-8804 or 540/687-8222; www.chrysaliswine.com), noted for its Albariño variety from Spain. It's open daily from 10am to 5pm.


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 complain they are often on "paddock princesses" -- who seldom ride but who like to look the part. 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 multimillions, 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.

Appropriately, Middleburg is home to the National Sporting Library, 102 The Plains Rd. (tel. 540/687-6542; www.nsl.org), a research center housing more than 16,000 books and periodicals about horse sports and fishing, some of them dating to the 17th century. It's open Tuesday to Friday 10am to 4pm, Saturday 1 to 4pm.

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, which purveys "home embellishments." I also grab a shot of caffeine at Cuppa Giddyup.

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."

Nearby Attractions -- Drive 1 1/2 miles north of Middleburg on C.R. 626 and you'll come to Glenwood Park (tel. 540/687-5662), Virginia's oldest racecourse in continuous use and home to many meets during the year, including the Virginia Fall Races in early October. Follow the gravel road uphill to the bleachers (look for the gazebo) for a gorgeous view of the Blue Ridge Mountains.

Nearby wineries are worth testing.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.