Northern Shenandoah Valley Road Trip: Winchester to Harrisonburg Virginia

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.

Scenic road Shenandoah Valley north
Scenic road Shenandoah Valley north

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.

Winchester Walking Mall Virginia
Winchester Walking Mall Virginia

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:

15 Fun Things to Do on a Winchester Virginia Getaway or Day Trip

For more information about things to do in Winchester and Frederick County, visit:
Winchester Frederick County Tourism | Facebook | Twitter

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.

Exploring fun things to do in Shenandoah County Virginia
Exploring fun things to do in Shenandoah County Virginia

Here are our 10 fun places to explore, eat, and drink in Shenandoah County:

10 Fun Things to Do in Shenandoah County Virginia

For more information about things to do in Shenandoah County, visit:
Visit Shenandoah County Tourism | Facebook | Twitter | Instagram

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.

Things to do in Harrisonburg Virginia
Things to do in Harrisonburg Virginia

Be sure to get a photo with Harrisonburg’s fun LOVEwork. Here are fun things to do in Winchester Virginia:

Favorite Things to Do in Harrisonburg Virginia and Rockingham County

For more information about things to do in Harrisonburg and Rockingham County, visit:
Harrisonburg Tourism | Facebook | Twitter | Pinterest | Instagram

Northern Shenandoah Valley Road Trip Tips

Country road Frederick County VA Shenandoah Valley
Country road Frederick County VA Shenandoah Valley

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 information about things to do on a road trip through the Shenandoah Valley, visit:
Visit Shenandoah Valley | Facebook | Twitter | Instagram

For more Shenandoah Valley tips and things to do, check out these related articles:

Follow Fun in Fairfax VA on FacebookTwitterPinterest, and Instagram for more fun places to visit and things to do in Northern Virginia and surrounding areas.

Portions of our Northern Shenandoah Valley road trip were hosted by Winchester Frederick CountyVisit Shenandoah County, and Harrisonburg Tourism. All opinions, text, and photos are our own.

A Northern Shenandoah Valley Virginia road trip offers scenery, hiking, local food and drink, history, unique stops, and time to unwind, not far from DC.

17 thoughts on “Northern Shenandoah Valley Road Trip: Winchester to Harrisonburg Virginia”

  1. This is not an area I am familiar with! Thank you for such a thorough tour! I saved it to Pinterest for future reference.

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