A Northern Shenandoah Valley road trip offers incredible scenery, delicious local food and drink, rich history, unique places to stay, and a chance to unwind, not far from Washington DC. Allow three to five days to explore the scenic area from Winchester to Harrisonburg, Virginia, avoiding the busy highway and enjoying beautiful country roads.
Explore and Escape in Winchester and Frederick County, Virginia
Begin your Northern Shenandoah Valley road trip in the historic downtown of Winchester. The Old Town Winchester Walking Mall is a lovely pedestrian area lined with unique stores, restaurants, museums, a nanobrewery, a theater, and historic buildings, including a tavern that George Washington frequented.
When you’re ready to explore further, take a slow drive along the country roads of Frederick County, stopping at local farms and wineries, or enjoying a hike along the West Virginia border. In summer, you can catch a flick at the Family Drive-in Theater, an old-school drive-in with car-mounted speakers. In fall, farms offer apple-picking, pumpkin patches, and other family-friendly fun.
Here are 15 fun things to do in and near Winchester Virginia:
Back Road Fun in Shenandoah County, Virginia
Heading south along Route 11 or smaller country roads, the next area to explore on a Northern Shenandoah Valley road trip is Shenandoah County, Virginia. Beautiful scenic roads, excellent hiking along the West Virginia border, local wine and beer on the Shenandoah Spirits Trail, small towns, and interesting museums give visitors plenty to do. We recommend at least two nights in the area if time allows.
Here are our 10 fun places to explore, eat, and drink in Shenandoah County:
Town and Country in Harrisonburg and Rockingham County Virginia
Our final stop in Northern Shenandoah County is Harrisonburg, home of James Madison University (JMU) and the county seat of Rockingham County. The Main Street Award winner has an historic downtown that is fun to explore on foot. Local restaurants and craft brewery offer relaxing places to stop and refuel before heading out for hiking and biking in Rockingham County.
Be sure to get a photo with Harrisonburg’s fun LOVEwork. Here are fun things to do in Winchester Virginia:
Northern Shenandoah Valley Road Trip Tips
Many people, like us, have traveled through the Shenandoah Valley on busy highway 81 without ever enjoying all that the region has to offer. To make the most of your visit:
- Get off the highway. Route 11 is the obvious alternate to route 81, since it parallels and criss-crosses the highway. But there are plenty of smaller, beautiful country roads that take you into the heart of the valley. Make time to explore a road less traveled
- Take it slow. The beauty of a road trip through Northern Shenandoah Valley is the change to see and experience something new. Enjoy the country roads; stop at a farm stand; visit a winery; poke around a small town.
- Extend the fun. If you allow extra time you can extend your road trip into Southern Shenandoah Valley or east onto Skyline Drive.
Have you explored the Northern Shenandoah Valley area of Virginia? We’d love to hear your tips on favorite stops for our next visit.
For more Shenandoah Valley tips and things to do, check out these related articles:
- Southern Shenandoah Valley Road Trips: Staunton to Lexington
- 8 Great Things to Do in Shenandoah Valley
- 8 Great Things to Do in Roanoke Virginia
- 8 More Wonderful Overnight Getaways Near Northern Virginia.