The View of the Shenandoah Valley From Little Stony Man, Shenandoah National Park, Virginia, USA

Exploring Virginia's Shenandoah Valley

When it comes to bucket-list worthy travel, Virginia’s Shenandoah Valley doesn’t disappoint. Stretching 200 miles from Winchester down to Lexington in the south, and flanked by the Blue Ridge Mountains to the east and the Allegheny Mountains to the west, this scenic corridor attracts more than 1.5 million visitors annually (including me!).

The drive from the Great Lakes region to Virginia’s Historic Triangle takes you through Winchester at the top end of “the Big Valley,” so be sure to schedule a few additional days to explore an area. It's a must-visit and time well spent.

Known as the “Breadbasket of the Confederacy” during the Civil War, the Shenandoah Valley played a pivotal role in supplying troops with food and resources, making it a highly contested area. Even before this devastating conflict, though, the valley played a hugely important role in American Independence, boasting a deep connection to important figures including George Washington and Thomas Jefferson.

Winchester: The Gateway to the Shenandoah Valley

len Burnie Historic House built in 1794 at the Museum of the Shenandoah Valley Photo by Bryan Dearsley .JPG
Glen Burnie Historic House was is included in a visit to the Museum of the Shenandoah Valley (Photo: Bryan Dearsley)

The Museum of the Shenandoah Valley (MSV) in Winchester, is a world-class facility where you can learn more about the region and its people. This magnificent state-of-the-art museum on the outskirts of Winchester chronicles the valley’s fascinating history through its large collection of artifacts from the colonial period, as well as the Revolutionary and Civil Wars. Not only that, during the American War of Independence, Winchester served as a key logistical center supplying troops, but during the Civil War it changed hands over 70 times between Union and Confederate forces, more than any other town during the conflict.

Next, visit Downtown Winchester, and after checking into the historic George Washington Hotel, take a peaceful stroll. Loudoun Street Mall is the centerpiece of Winchester’s Old Town district, a car-free, red brick pedestrian-only throughfare that slices through the 45 blocks of this National Register Historic District. Stretching for half a mile, it’s lined with eateries, boutiques, as well as attractions like the Shenandoah Valley Civil War Museum, as well well-preserved old homes dating back to the town’s early years.

Old Town Wnchester Photo by Bryan DearsleyJPG
Old Town Wnchester's pedestrian zone is perfect for a stroll (Photo: Bryan Dearsley)

Then head to George Washington's Office. Located near the south end of Loudon Street and only a 15 minute walk from the hotel, this historically significant (though modest) log cabin served as Washington’s military headquarters from 1755 to 1756. It was here, in his early twenties, that the future President was tasked with overseeing the construction of a series of frontier forts to protect settlers from raids during the French and Indian War.

Suffice to say, Winchester has so many things to see and do. But don't go without first visiting two recommended local eateries. Knead Bread offers excellent lunch-to-go from charming servers and Bonnie Blue Southern Market & Bakery offers a slap up breakfast in what used to be a gas station. And the New York Times was right: their biscuits and sausage gravy with fried local apples really was fantastic.

The Magnifient Luray Caverns

The Luray Caverns stalilmites photo Bryan Dearsley
The spectacular Luray Caverns are a sight to behold (Photo: Bryan Dearsley)

There’s a long tradition of tourists wanting to visit Virginia’s subterranean world. And no one does it better than the folks at Luray Caverns. An hour drive south of Winchester along the scenic Stonewall Jackson Highway, these spectacular caverns are one of the most visited natural attractions in the state, drawing tourists since its discovery in 1878. The site’s 1.25-mile path through subterranean landscapes takes you past the massive Titania’s Veil, a dazzling white flowstone formation, and Dream Lake, a crystal-clear mirror-like pool of water that produces an altogether otherworldly effect.

Other highlights included the spectacular Double Column, a towering stalactite and stalagmite structure reaching over 40 feet high; and perhaps the cavern’s most remarkable feature, the “Great Stalacpipe Organ,” a musical marvel that produces ethereal tones by striking stalactites of varying sizes.

Great Stalacpipe Organ photo by Bryan Dearsley
The world famous Great Stalacpipe Organ sounds eerily beautiful (Photo: Bryan Dearsley)

Above ground, explore the Car and Carriage Caravan Museum, an impressively large collection of horse-drawn vehicles and vintage cars including an 1897 Mercedes-Benz, one of the oldest in the country. Toy Town Junction, a nostalgic exhibit of model trains and classic toys, is fun for kids, while the Luray Valley Museum presents the cultural history of the Shenandoah Valley through restored 19th-century buildings and historical artifacts.

After spending a day at the caverns, check out Mimslyn Inn for a good night's rest. Located just a short drive from downtown Luray (you could walk, but it’s around 30 minutes each way), this elegant property was built in 1931 in colonial-style and features classy, comfortable rooms. The hotel has an on-site restaurant and Speakeasy Bar, to unwind with a tasty cocktail.

Shenandoah National Park and Skyline Drive

Shenandoah National Park and Skyline Drive Photo by Bryan Dearsley
Tackling the Skyline Drive is a Shenandoah mmust-do (Photo: Bryan Dearsley)

Day three of exploring the Shenandoah Valley was a 39-mile section of the iconic Skyline Drive. While only a portion of the 105-mile scenic road that spans the entire length of Shenandoah National Park (from Front Royal in the north to Swift Run Gap Entrance Station in the south), it was to prove an incredible introduction to one of Virginia’s best scenic drives.

This fun route is a feast for the eyes, with spectacular views at every turn. In this three hour drive, there are well over 20 overlooks to stop at. Some of these include Mary’s Rock Tunnel Overlook and Pinnacles Overlook, both boasting great views of the Blue ridge Mountains. Some favorites, though, are those that include views over Shenandoah Valley itself, with highlights including Franklin Cliffs Overlook, where you can clamber over some rocks for an unobstructed view of the “Big Valley,” and the Oaks Overlook, especially beautiful as fall colors beautifully frame the valley far below.

Shenandoah National Park and Skyline Drive Overlook  Photo by Bryan Dearsley
Be sure to make the most of the many overlooks along Skyline Drive (Photo: Bryan Dearsley)

For those wanting to spend longer in Shenandoah National Park, park services have you covered. Wander around Skyland Resort, a lovely mountain retreat that provides accommodations from rustic lodges to more modern hotel units, the best of which have private balconies overlooking the valley.

Available activities include horseback riding along scenic mountain trails (suitable for novice and experienced riders), and plenty of hiking, while there’s also a conference center available for functions. Prefer camping? Big Meadows Campground offers developed campsites with amenities (think washrooms and showers), as well as resort style accommodations.

Harrisonburg and Massanutten

Edith J. Carrier Arboretum and pond photo by Bryan Dearsley
The Edith J. Carrier Arboretum is a great spot for a quiet stroll (Photo: Bryan Dearsley)

The Shenandoah Valley's Harrisonburg is a wonderful place to explore on foot. Founded in 1779, this delightful university town has a year-round population of just over 50,000 citizens along with some 23,000 students. Located on the grounds of James Madison University, the Edith J. Carrier Arboretum is a peaceful public park that is great for a stroll, especially as the leaves are peaking.

In downtown Harrisonburg, visit Hardesty-Higgins House, built in 1848. It is a centerpiece of the town's historic district and once served as the home to the town's first mayor. Now a visitor center offering useful info and ideas to travelers, it’s also home to the Civil War Orientation Center detailing the area’s wartime past.

Court Square om Harrisonburg Photo by Bryan Dearsley
Harrisonburg's photogenic Court Square (Photo: Bryan Dearsley)

The star of the show, though, is Court Square with its charming setting and historic buildings. Anchoring the city's historic district, this picturesque space has been the community's central gathering point since the town's founding and features the striking Rockingham County Courthouse, an architectural gem that you can view from every angle by walking around the square’s perimeter. Located nearby, the Virginia Quilt Museum showcases both historical and modern textile artistry and is well worth popping in to.

Spend the night in nearby Massanutten Resort. Spread across 6,000 acres and just 15 miles from downtown Harrisonburg, this sprawling four-season resort is a destination in itself. Accommodations consist of a luxurious two-bedroom townhouse with a fully equipped kitchen, a huge living room with fireplace, a dining room, and a good-sized porch with a BBQ and spectacular views of the surrounding hills. Topping it all is a luxurious master bedroom with a sumptuous king bed and a huge bathroom with a bathtub. Add to this a glorious sunset, and it is the perfect end to perfect day.

The sunsetting over my digs at Massanutten Resort Photo by Bryan Dearsley
The spectacular sunset from my digs at Massanutten Resort (Photo: Bryan Dearsley)

While it make take a few extra days to see everything at this resort (it’s vast), be sure to enjoy a wonderful breakfast at the Campfire Grill. Located in the same building as the clubhouse of the Mountain Greens Golf Course, this buffet-style feast will leave you set for the next leg of your adventure: a morning stop in the lovely small town of Lexington before heading to Virginia’s Colonial Triangle.

Tips And Tactics

For ideas and inspiration about travel to these and other beautiful spots in the Shenandoah Valley region of Virginia, check out these useful resources:

Visit Virginia: www.virginia.org/places-to-visit/regions/shenandoah-valley/

Visit Winchester: https://visitwinchesterva.com/

Museum of the Shenandoah Valley: https://www.themsv.org/

Luray Caverns: https://luraycaverns.com/

Shenandoah National Park: https://www.nps.gov/shen/index.htm

Visit Harrisonburg: www.visitharrisonburgva.com/

Massanutten Resort: https://www.massresort.com/

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