Virginia is for lovers, and people fall head over heels for the Old Dominion itself in the fall. As leaves blaze red, orange, and yellow, the historic communities seated in the mountains and countryside fire up their event calendars, giving visitors tons to see and do. Get your fill on a road trip packed with gorgeous views, scenic drives, little towns, farms, and vineyards.
Just a 45-minute drive southwest of Washington D.C. lies Skyline Drive. The 105-mile-long stretch of public road snakes through Shenandoah National Park and gives way to breathtaking views of fall foliage atop the Blue Ridge Mountains. Pause at one of many overlooks for leaf peeping and glimpses of deer and black bear.
Squeeze a little kitsch into your schedule at the roadside attraction of Foamhenge. Fiberglass artist Mark Cline created the Styrofoam replica of Stonehenge that sits adjacent to Natural Bridge, a 20-story solid rock bridge surrounded by wooded trails.
Ramble slightly further south to the sleepy but recently revitalized town of Staunton, known as the birthplace of Woodrow Wilson. The small valley town – fancifully dappled with rows of two- and three-story brick buildings erected before the Civil War – brims with cute stores and restaurants like Staunton Grocery, serving locally-sourced ingredients in Southern dishes like rhubarb-glazed quail.
For a different trek, head west from D.C. and follow Route 50 about 40 miles right to charming Middleburg and surrounding horse country. Small, early-American buildings flank the pastoral town’s main drag, Washington Street. Here you’ll mingle with nattily dressed equestrians as you peruse art galleries and shops for the horse-loving set. Fill a picnic basket with seasonal nibbles at casual yet decidedly gourmet lunch spots, including Market Salamander.
Jockey for position (aka: front-row seats) at The Virginia Fall Races, the esteemed horse runs held yearly in early October at Glenwood Park. Capping off the racing season is the Gold Cup Race on October 16. Everyone from college students to DC power players to local farm owners gets decked out to tailgate and watch the steeplechase action.
Tucked in the outskirts of Middleburg rest local vineyards that have made a name for themselves and pushed Virginia wines to the top of the list. Our favorite: The Boxwood Winery in Piedmont, for its accommodating tasting room and luscious Hunt Country Chardonnay (handily available by the case).
Written by Washington D.C. contributor Annie Lou Bayly Berman