At the heart of Virginia’s hunt country lies Middleburg, a one-stoplight town that has changed little since it was founded in 1787, a picture postcard village for spending a quiet afternoon walking the streets.

A central gathering place for the wealthy owners of nearby farms and equestrian operations and students from the region’s private schools, Middleburg contains tack shops, antiques stores, and boutiques as well as a number of restaurants, including the Red Fox Inn, which began as Mr. Chinn’s Ordinary in 1728 and continues to operate as a tavern and inn today, making it one of the country’s oldest, visited in 1748 by a young George Washington.

In late May, farms throw open their barn doors for the Hunt Country Stable Tour (www.middleburgonline.com), revealing the pampered lives of the Loudoun County’s thoroughbreds and point-to-point steeds. The first weekend of October is time for the Virginia Fall Races (www.vafallraces.com)—exciting steeplechase races that have participants taking on huge jumps and water obstacles as well as racing on the flat.

Virginia’s Vineyards

Virginia’s efforts to become a world-renowned wine region can be traced to the failed effort by Jamestown settlers to cultivate grapes and Thomas Jefferson’s more vigorous effort—growing grapes for 30 years at Monticello—that never produced a single bottle of wine.

In the 1870s the state finally received recognition at the Vienna World’s Fair for a vintage made from Virginia’s only fine native grape, Norton, and finally, in the 1970s, a number of wineries began to take root. Today, the state has 140 wineries, several of which are within minutes of Middleburg and Leesburg. The state’s most notable wines are its viognier, cabernet franc, and Norton.

Among the award-winning wineries are Chrysalis Vineyards (23878 Champe Ford Rd., Middleburg, Va., 540/687-8222, www.chrysaliswine.com, daily 10 a.m.-5:30 p.m., tasting $5), known for its Norton, viognier, and albarino varietals; Piedmont Vineyards (2546D Halfway Rd., The Plains, Va., 540/687-5528, www.piedmontwines.com, daily 11 a.m.-6 p.m., tasting $5), one of the pioneers established in 1973 and known for its chardonnay, white wines, and fruit wines, including peach; Boxwood Winery (2042 Burrland Rd., Middleburg, Va., 540/687-8778, www.boxwoodwinery.com), which offers tours and tastings by appointment at the winery and has a tasting room in Middleburg, and is hailed for respectable reds; and Willowcroft (38906 Mount Gilead Rd., Leesburg, Va., 703/777-8161, www.willowcroftwine.com), closer to Leesburg with beautiful views and a variety of white and red wines.

Aldie Mill

On the drive to Middleburg along U.S. 50, visitors pass Aldie Mill (39401 John Mosby Hwy., Aldie, Va., 703/327-9777, www.nvrpa.org/park/aldie_mill_historic_park, mid Apr.-late Nov. Sat.-Sun. afternoon, free), Virginia’s only tandem-waterwheel mill. Restored in 2010, the mill complex consists of the mill, a granary, and a storehouse. During the Civil War, miller John Moore (only one of five men in Aldie to vote against secession) provided grain to the Union; his son, a Southern sympathizer, sold grain to Confederate troops. Now owned by a regional park authority, the mill hosts an art show each weekend in September to benefit restoration of the facility.

Sky Meadows State Park

In the fall, Sky Meadows State Park (111012 Edmonds Lane, Delaplane, Va., 540/592-3556, www.dcr.virginia.gov/state_parks/sky.shtml, Apr.-Oct. Mon.-Fri. 11 a.m.-5 p.m., Sat.-Sun. 10 a.m.-6 p.m., Nov.-Mar. Mon.-Fri. 11 a.m.-4:30 p.m., Sat.-Sun. 10 a.m.-4:30 p.m.) burns in golds, reds, and browns, with views of wooded hills and rolling farmland. In the spring the trees burst forth in new green and wildflowers and shrubs bloom alongside the Appalachian Trail, which crosses the park at roughly 2,000 feet in elevation.

If all the driving around the Virginia countryside has you itching to get out and walk, Sky Meadows has 12 miles of hiking trails ranging from moderate to difficult. Located not far from the charming villages of Paris and Delaplane, Sky Meadows also has a one-acre pond for fishing and offers numerous nature-oriented tours and activities on weekends.