4 Best Sights in Northern Virginia, Virginia

Founded in 1758 at the crossroads of two Native American trails near the Potomac, the hub of Loudoun County retains its historic charm but is totally immersed in the present day. Funky and fun boutiques, coffee shops, stylish bars, and farm-to-fork restaurants housed in historic buildings line its picturesque streets. The interactive Loudoun Museum has rotating exhibits, tours, and talks on everything from the Revolutionary War in Loudoun to the origins of the Virginia wine industry. Leesburg is a good base from which to explore Loudoun’s historic sites, small towns, and wineries.

In the heart of Virginia’s hunt and wine country, Middleburg is a welcoming country town that Elizabeth Taylor and Jackie Kennedy (and plenty of other illuminati) have called home. It dates back to 1728 when a cousin of George Washington established a fieldstone tavern on an old Native American trail; that tavern, Red Fox Inn, is still going strong. Boutiques, antiques stores, restaurants, taverns—and a craft distillery—line the enchanting Main Street (US 50), while a bevy of wineries and breweries sprinkle the surrounding countryside. The Middleburg Film Festival is a major stop on the Oscar trail, while in December the town turns into a scene from a Charles Dickens novel, with carolers, actors, and musicians.

Two-lane roads—and plenty of dirt and gravel lanes—lace Loudoun County, connecting a bevy of picturesque small towns full of historic charm. Don’t miss Purcellville, graced with Victorian homes dating back to 1874 when the railroad came through; Hillsboro, known for its quintessential stone buildings; Round Hill, where wealthy Washingtonians once escaped the summer heat; and Waterford, settled by Quakers and the site of a long-running fall arts festival. Along the way, you’ll discover pick-your-own farms, grazing horses, antique shops, breweries, wineries, country B&Bs, and more.

Dating back to 1733, this National Historic Landmark village is a good example of 19th century life in Loudoun County. The Waterford Foundation has a self-guided walking tour of the town—stop by the Visitor Center at the Corner Store for town information. The walking tour is also available online.