Scenic road Shenandoah Valley north

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

Things to Do in Winchester and Frederick County

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


With only an hour in town, we barely scratched the surface of all there is to see. You could easily spend a day exploring the Walking Mall and nearby Patsy Cline House, Handley Library, Old Court House, and other attractions.

When you’re ready for a little exercise and a lot of view, drive west of town and hike to Eagle Rock on the Tuscarora Trail. The trail climbs for 1.5 miles on a moderately steep and rocky trail to a series of rock outcroppings with stunning views. One overlook even has a stone bench that would make a good picnic spot on this 3 mile out-and-back hike.

Eagle Point Overlook Winchester VA

Eagle Point Overlook Winchester VA


The trailhead for the hike is a little hard to find via GPS, so here is a map to the turn onto Capon Springs Grade/route 609. Follow the dirt road uphill until you see a small parking area on your left, just before the West Virginia line. The trail begins across the street, marked with a Great Eastern Trail sign.

Stop at Richard’s Fruit Market, on route 628 in Middletown, to pick up farm fresh treats. This 5th generation farm proudly sells their own beef, apples, produce, jams, and other goodies. They also have a pick-your-own flower garden, animals to visit, and a very cool apple grader that buffs and sorts the apples.

Richards Fruit Market apples Shenandoah Valley north

Richards Fruit Market apples Shenandoah Valley north


In summer, you can catch a flick at the Family Drive-in Theater, an old-school drive-in with car-mounted speakers.

Tour the mansion at Belle Grove Plantation, an antebellum farm once owned by Isaac and Nelly Hite. Nelly was the sister of future president James Madison. Tours share details of life on the plantation during the early 1800s, and the period architecture and furnishings of the manor house. Outside, visitors can stroll the gardens and grounds in the pastoral country setting in Middletown.

Belle Grove Plantation view Shenandoah Valley north

Belle Grove Plantation view Shenandoah Valley north


Drink and Eat Local in Winchester and Frederick County

Enjoy breakfast at Steamy’s Cafe, an eclectic local meeting place serving homemade bagels and tasty sandwiches. The owner, Lenny, calls himself “Winchester’s ambassador,” and he’s happy to offer advice on things to do in town.

Steamy's Cafe Winchester VA

Steamy’s Cafe Winchester VA


For a delicious and filling lunch or dinner, you can’t beat the authentic cajun food at Sweet NOLA’s at the north end of downtown. Owner Cheryl Ash prepares authentic New Orleans dishes, tasty po’ boys, and weekly specials. If you have a sweet tooth, try the Krispy Kreme bread pudding. Cheryl also books high energy music, so check their Facebook page for the latest events.

Sweet NOLA's Winchester VA

Sweet NOLA’s Winchester VA


Where to Stay in Winchester and Frederick County

The Inn at Vaucluse Spring is the perfect base for exploring the Winchester area, especially if you’re looking for romance and relaxation. Located in the small town of Stephen’s City, just south of Winchester, there are six different guest houses to choose from.

Inn at Vaucluse Spring, Stephens City Virginia

Inn at Vaucluse Spring, Stephens City Virginia


We highly recommend the historic Mill House, with fireplace, small kitchen, bedroom with expansive windows, jacuzzi tub, and best of all, a private patio overlooking the small pond fed by Vaucluse Spring. Breakfast in the manor house is three courses of farm-to-table deliciousness, and guests rave about the prix fixe dinners.

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.

Things to Do in Shenandoah County

One of the best views in the area is a steep, two-mile hike up to a ridge and rocky summit on Big Schloss in the Wolf Gap Recreation Area (4 miles out and back). During the fall, foliage views from the summit are absolutely outstanding.

Big Schloss Summit

Big Schloss Summit, Northern Shenandoah Valley Virginia


The Woodstock Tower Trail in Woodstock offers dramatic westward views with a much shorter hike. The challenge here is the steep, dirt road that switchbacks it’s way to the tower. Unfortunately, we were stopped short of the summit by a stuck RV (not a good place to bring an RV!) so we’ll have to visit on a return trip.

Enjoy heights of a different sort from a footbridge over the North Fork Shenandoah River on Chapman Landing Road. The 24-foot high bridge, used by locals to reach work and school when the low concrete bridge is flooded, is fun to explore from the Inn at Narrow Passage (info below).

Suspension bridge Shenandoah Valley north

Suspension bridge Shenandoah Valley north


The Shenandoah Heritage History Museum at Edinburg Mill is packed with engaging and diverse displays about the heritage of the valley ($3 admission). Learn about how transportation and travel evolved on the great valley pike, aka route 11, from its early use by Native Americans, to its near destruction during the Civil War, to it’s current use connecting towns throughout the valley.

Edinburg Mill Museum Shenandoah Valley north

Edinburg Mill Museum Shenandoah Valley north


Continue south on Route 11 to Mount Jackson and turn left on route 720 to reach the beautiful Meem’s Bottom Covered Bridge, a 204-foot single-span Burr arch truss across the North Fork. The bridge has been burned and rebuilt several times, but it retains it’s architectural charm. Visitors like to drive and walk through the bridge, so approach with caution.

Meems Bottom covered bridge Shenandoah Valley north

Meems Bottom covered bridge Shenandoah Valley

Meems Bottoms covered bridge interior Shenandoah Valley north

Continue under highway 81, and turn left on 950 to reach Route 11 Potato Chips, which moved from its earlier route 11 location. You can’t tour the factory, but you can watch the process through large windows. Best of all, chips are available to sample and purchase.

Route 11 Potato Chips Shenandoah Valley Virginia

Route 11 Potato Chips, Shenandoah Valley Virginia


Drink and Eat Local in Shenandoah County

Woodstock Garden Cafe is a nice stop for lunch, especially when the weather is warm and you can enjoy a table in the greenhouse. Enjoy sandwiches, salads, and daily specials in a relaxed, casual setting.

Woodstock Garden Cafe Northern Shenandoah Valley

Woodstock Garden Cafe, Northern Shenandoah Valley


In the center of town, Woodstock Brewhouse, offers a nice selection of Virginia craft beer along with huge pretzels and tasty flatbread pizzas. The open space is hopping on Thursday nights when live music amps up the volume and the energy.

Woodstock Brew House Northern Shenandoah Valley

Woodstock Brew House Northern Shenandoah Valley


Beans Barbecue serves huge plates of pulled pork, ribs, and beans in a barebones setting in an old firehouse in downtown Edinburg.

Beans Barbecue Edinburg Shenandoah Valley north

Beans Barbecue Edinburg Shenandoah Valley north


Another stop on the Shenandoah Spirits Trail is Shenandoah Vineyard, one of the earliest wineries in Virginia. Jim and Emma Randel first planted their vines in 1976 and Emma still presides over the business. Enjoy a tasting in the barn or take a seat on the patio and soak in the view.

Shenandoah Vineyard Woodstock Virginia

Shenandoah Vineyard Woodstock Virginia


Further southwest in the little village of Quicksburg, Third Hill Winery at De Mello Vineyards operates out of a beautiful barn with expansive patios and vineyard views. The warm climate produces tasty red wines like Chambourcin and Cabernet Franc, and we are fans of their Viognier. Try one of the Chambourcin-filled chocolates for a delicious treat.

DeMello Vineyards Northern Shenandoah Valley

DeMello Vineyards Northern Shenandoah Valley


Where to Stay in Shenandoah County, Virginia

Edinburg makes a nice home base for exploring Shenandoah County, and the Inn at Narrow Passage has been welcoming guests for many years. The inn offers 12 rooms, many with fireplaces and canopy beds, plus larger bedrooms that are ideal for families.

Inn at Narrow Passage lawn, Edinburg VA

Inn at Narrow Passage lawn, Edinburg VA


The patio and lawn are perfect for relaxing, and you can walk down the road to try the footbridge above the North Fork river.

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.

Things to Do in Harrisonburg and Rockingham County

Start your visit at the Hargesty Higgins House Visitor Center, which has an excellent orientation center, a small museum about the historic Valley Turnpike (route 11), a gift shop, and a small cafe. Pick up a map and explore the historic downtown on foot. Harrisonburg was the Great American Main Street Award Winner in 2015.

Visitor Center Harrisonburg VA

Visitor Center Harrisonburg VA


Be sure to get a picture at the Harrisonburg LOVEwork, behind the Virginia Quilt Museum. The LOVEwork highlights four cultural themes of diversity, agriculture, recreation, and arts.

LOVEwork Harrisonburg Virginia

LOVEwork Harrisonburg Virginia


Harrisonburg is a popular biking area, and one of the local bike shops in town—Shenandoah Bicycle CompanyRocktown BicyclesBluestone Bike & Run—can offer advice and gear for your own bike outing.

If you prefer a hike, ask the Visitor Center for advice and trail maps. We drove west  to the Hone Quarry area of the George Washington National Forest for a short but fairly steep half-mile hike to a spectacular viewpoint.

Trail Hone Quarry overlook Rockingham County VA

Hone Quarry overlook trail Rockingham County VA

Hone Quarry Overlook Rockingham County VA

Hone Quarry Overlook Rockingham County VA


For a short walk through nature in town, visit JMU’s Edith J Carrier Arboretum. The network of paths, with benches for relaxing, is a nice place for a break.

Arboretum Harrisonburg VA

Arboretum Harrisonburg VA


Drink and Eat Local in Harrisonburg and Rockingham County

Bella Luna serves delicious wood-fired pizzas using fresh, local ingredients in the historic Livery Building downtown. They also offer a nice selection of fresh salads and sandwiches, and the vibe is warm and relaxed. If you’re in the mood for a treat, head across the street for some of Bella’s tasty gelato, made with milk from a local dairy.

Bella Luna pizza Harrisonburg VA

Bella Luna pizza Harrisonburg VA

Bella gelato Harrisonburg Virginia

Bella gelato Harrisonburg Virginia


Another option for dinner in town, Clementine’s Cafe brings food, music, and art together. The outdoor downstairs patio was quiet during our dinner, but trivia nights and live entertainment bring a crowd on weekends. Closer to JMU, we like Corgans Publick House for Irish specials, good burgers, and a pint.

Downtown Harrisonburg is home to four of the craft breweries on the Shenandoah Spirits Trail and the BeerWerks TrailPale Fire Brewing CompanyBrothers Craft BreweryThree Notch’d Brewing Company, and Wolfe Street Brewery. Pale Fire Brewing opened in 2015 in the renovated Ice House, a cool industrial building, and has a nice open tasting room and patio. We tasted 5 of the 11 brews on tap, and particularly liked the Red Molly and the Lucille Irish Stout.

Pale Fire Brewing Harrisonburg VA

Pale Fire Brewing Harrisonburg VA


Where to Stay in Harrisonburg Virginia

The comfortable Fairfield Inn and Suites is a good option for a stay in Harrisonburg. It’s located near James Madison University and the Arboretum, just a short drive from downtown.

Fairfield Inn and Suites Harrisonburg VA

Fairfield Inn and Suites Harrisonburg VA


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 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:

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

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.

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21 Responses to “Northern Shenandoah Valley Road Trip: Winchester to Harrisonburg Virginia”

  1. Susanna November 15, 2016 at 3:03 pm #

    Great article! However the Library in Winchester us the Handley Library not Hanley. 😀

    • Fun in Fairfax VA November 15, 2016 at 3:48 pm #

      Thanks so much for catching that typo (now fixed)! Thanks for the positive feedback too, Susanna. 🙂

  2. Doreen Pendgracs November 15, 2016 at 7:30 pm #

    I have never been to Virginia, but would love to visit. Your post makes everything look SO scrumptious! I’m sure I would gain 10 pounds.

  3. suzannestavert November 15, 2016 at 8:24 pm #

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

    • Fun in Fairfax VA November 15, 2016 at 10:00 pm #

      Thanks for the positive feedback Suzanne. It really is a beautiful area.

  4. Ed November 15, 2016 at 9:55 pm #

    Great article showing what we have to offer in our valley. Thanks 3rh hill winery@ DeMello vineyards

    • Fun in Fairfax VA November 15, 2016 at 10:02 pm #

      Thanks Ed. We loved our visit to 3rd Hill Winery at DeMello Vineyards. That’s quite a tasting barn you built! The Shenandoah Valley is lovely.

  5. Polly November 17, 2016 at 8:05 am #

    Lovely! I’m originally from Berryville, so this is making me so homesick! Can’t wait to come back and visit.

    • Fun in Fairfax VA November 17, 2016 at 8:36 am #

      Thank you Polly. I can understand being homesick for such a beautiful and fun area. Hope you get back to visit soon.

  6. McCool Travel November 17, 2016 at 4:06 pm #

    Shenandoah Valley is road trip heaven. Scenic roads that are hilly and curvy, leading to all kinds of local food and beverage experiences. I may go back sooner than expected.

  7. Liz @ I Heart Vegetables November 18, 2016 at 11:44 am #

    Wow it looks absolutely gorgeous! I’m ready for a road trip!

    • Fun in Fairfax VA November 18, 2016 at 2:04 pm #

      Thanks Liz, hope you have a great road trip!

  8. emma November 18, 2016 at 4:26 pm #

    If I’d had it my way, I would have moved out here instead of Fredericksburg 🙂 These photos are amazing!

    • Fun in Fairfax VA November 20, 2016 at 9:21 am #

      Thanks Emma! Fortunately, it’s close enough for a day trip (though we suggest an overnight or more). Happy exploring!. 🙂


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