Just 1.5 hours from Washington, DC is one of Virginia’s most scenic counties, a lush and peaceful valley filled with history, caverns, and wineries. Bordered by the Massanutten Mountains to the east and the Alleghenies to the west, and bisected by the winding curves of the Shenandoah River, Shenandoah County was first settled by Pennsylvania Germans in the mid-18th century, and you can find history everywhere, from the preserved cemeteries of former slaves to 18th-century courthouses possibly designed by Thomas Jefferson. 

Consisting of six towns and cities that include Woodstock and Fort Valley, Shenandoah County played a role in both the American Revolution and Civil War. Some even say that George Washington ordered the building of the first road into Fort Valley during the American Revolution, and he named the city of Woodstock too, the historic heart of the valley known for its unique shops and hiking trails.

It’s not just history that defines the valley; it’s known for its outdoor adventures, particularly since Shenandoah County is a gateway to the George Washington National Forest, a massive 1.8 million-acre area stretching across Virginia and West Virginia. Shenandoah County contains over 75,000 of those acres, with 178 miles of trails winding through the pristine beauty of the Blue Ridge Mountains. Besides that, you can float or fish the river in the Seven Bends State Park or head down into the majestic Shenandoah Caverns, one of the many caves you can find in this karst-filled landscape that is partly what has made Virginia’s cave system so world-famous.

Besides its natural beauty, Shenandoah County is becoming more and more recognized for its wine-making. The county is part of the larger Shenandoah Valley, whose viticulture goes back to the 19th century, as people realized that the cooler climate of the Blue Ridge slopes and microclimates of the valley were ideal for wine-making. Thomas Jefferson was the first to make wine in Virginia, and while he did so in the Monticello wine region, another one of Virginia’s breathtaking destinations, it’s certainly not the only place in the state to offer top-notch wines. Shenandoah County has a handful of high-quality vineyards, which offer a variety of flights and views of the Blue Ridge Mountains, plus sustainable practices.

One of the favorite vineyards in the county is Star in the Valley Winery in Strasburg, whose 4.9 rating on Google comes from its quieter, off-the-beaten-path vibe, warm hospitality, and stellar mountain views. The owners of Star in the Valley are a husband and wife who were lawyers for the Department of Justice’s Environment and Natural Resources Division, so sustainability is a high priority for this vineyard, which grows its grapes on its estate and has a tasting room where you can purchase wines, all of which removes the carbon footprint of transporting grapes and bottles. 

Cave Ridge in Mount Jackson has a 4.7 rating on Google, with visitors praising its unlimited views, dog-friendly atmosphere, and the fact that it has “one of the best food menus around with such a satisfying charcuterie board.” Customers have given Muse Vineyards in Woodstock 4.6 stars on Google for its trail-filled estate that even includes a swinging bridge. This vineyard opts for hand-done practices where possible instead of using heavy machinery as part of their sustainability effort.

While you could visit Shenandoah County at any time of year to experience its seasonal beauty, some believe that the best time to experience the area is from the late spring through the early autumn. Springtime of course brings its blooms, while summer is a good time to partake in the county’s variety of outdoor recreational activities. Visitors in the summer can enjoy the live music at the Shenandoah Valley Music Festival, whose symphonic beginnings in 1963 have transformed over time to rock, pop, and bigger acts like the Village People, Beach Boys, and Judy Collins.

The closest major airport is Dulles International Airport, about 1.5 hours away, although there’s also the regional option of Shenandoah Valley Airport below the southern part of the county, about 35 minutes from New Market. United Express serves the Shenandoah Valley Airport, and SkyWest will begin flying there in 2026. Once there, the best way to explore this scenic area is by car. This way, you can take advantage of all it has to offer and see sites like the Meems Bottom covered bridge, one of Virginia’s most famous covered bridges that you can still drive through, and get your piping hot fresh potato chip on with a visit to the Route 11 potato chip factory.