8 Great Things To Do In Shenandoah Valley Virginia • McCool Travel

Some of the most memorable and best things to do in Shenandoah Valley include gorgeous scenic drives and breath-taking hikes on ands near Skyline Drive and Blue Ridge Parkway, staying in romantic hotels, and sampling USA’s best craft beer.

Shenandoah Valley Virginia is an area of astounding natural beauty and amazing history. For your next Virginia vacation, consider the following cool, happy, and fun Shenandoah Valley attractions.

Where is Shenandoah Valley? Shenandoah Valley is located between two mountain ranges—Blue Ridge mountains to the east and Allegheny (Appalachian) mountains to the west—and stretches 200 miles—from the Potomac River in the north to the James River in the south.

This custom map of Shenandoah Valley shows places mentioned in this article.

More than 45 million US residents can trace their family history and heritage to ancestors who lived or migrated through Shenandoah Valley Virginia. I can! How about you?

Oh, and I do not even include any things related to one of USA’s most famous rivers, the mighty Shenandoah River.

Things to Do in Shenandoah Valley Virginia

Did you know that George Washington had his first job, won his first election, and had his earliest military encounters in Shenandoah Valley?

Shenandoah Valley is also the birthplace of the most educated US President (Woodrow Wilson) and a country music legend (Patsy Cline), along with the final resting place of Lord Fairfax (owner of 5.5 million acres of pre-Colonial Virginia) and Civil War generals Robert E. Lee and Stonewall Jackson.

Using Visit Virginia current regions, Shenandoah Valley stretches 150 miles from the Virginia border (north of Winchester) to just south of Natural Bridge, and includes the Virginia counties of Augusta, Clarke, Frederick, Page, Rockbridge, Rockingham, Shenandoah, and Warren. Historically, Shenandoah Valley stretches south to Roanoke but I am following the current Visit Virginia designation.

Thank you to various tourism departments for inviting the McCool Travel team to experience Shenandoah Valley. I was not otherwise compensated and this content represents my independent thoughts.

These Shenandoah Valley attractions are listed as you travel from north to south. 

1. Tuscarora Trail

While the AT—Appalachian Trail that is—is still the king of hikes, the Tuscarora Trail is a worthy substitute throughout Shenandoah Valley. In fact, the Tuscarora Trail has been in development for many years and is now a complete AT bypass, covering 220 miles from Shenandoah National Park to Harrisburg, Pennsylvania.

As Visit Winchester says, “The Tuscarora Trail is truly a hidden gem, but may not remain so once people realize there’s alternative for Old Rag to get beautiful valley vistas.” We hiked to Eagle Rock, from a nondescript parking lot on the VA/WV border and had the trail and beautiful valley vistas to ourselves. In October. This trail is truly a Virginia hidden gem. As local legend Patsy Cline crooned, CRAZY. Tuscarora Trail is managed by Potomac Appalachian Trail Club.

After hiking the Tuscarora Trail, a magnificent place to eat in Winchester Virginia is Sweet NOLA’s. NOTE: Sweet Nola’s is now closed but the owner/chef now works over at The George Washington in Winchester.

2. Skyline Drive and Blue Ridge Parkway and Shenandoah National Park

Only in Shenandoah Valley can you visit Skyline Drive and Blue Ridge Parkway in the same day (or even hour). You can also walk for days—or an hour—on the most famous hike in the United States (Appalachian Trail), visit several caverns, and explore endless gorgeous small, scenic, country roads.

— Shenandoah National Park

Shenandoah National Park is one of the most accessible US National Parks, located only 75 miles from Washington, DC. Skyline Drive runs 105 miles, along the entire length of Shenandoah National Park. There are dozens of majestic scenic stops with access to hundreds of miles of hiking trails in the Shenandoah Mountains.

Plan your Shenandoah Park visit: Shenandoah National Park Day Trip Planner.

— Skyline Drive / Blue Ridge Parkway

Many have called Skyline Drive the greatest scenic drive in America, especially in fall when the colors are changing. At the southern end of Skyline Drive and Shenandoah National Park, continue your glorious long road trip on Blue Ridge Parkway for another 469 miles. During many Skyline Drive and Blue Ridge Parkway road trips, we have seen bicyclists, motorcyclists, classic cars, and vehicles of all types. If you drive all 574 miles of Skyline Drive and Blue Ridge Parkway, congratulations, you have covered about 25% of the Appalachian Trail—which parallels and meanders along both scenic roads. Oh, we have also seen black bears bumbling across the road and trails.

3. Shenandoah Spirits Trail / BeerWerks Trail

Sticking with the trail theme, after some Tuscarora Trail hiking and Skyline Drive driving, Shenandoah Valley has dozens of places to quench your thirst. While some places have been operating for many years, the newly launched Shenandoah Spirits Trail and Shenandoah BeerWerks Trail links them together for a better tourist experience.

The Shenandoah Spirits Trail offers something for every adult. The trail includes 27 wineries, breweries, cideries, and distilleries between Winchester and Harrisonburg. Most also offer food (local Route 11 potato chips, if nothing else) along with non-alcoholic beverages (like craft root beer or ginger beer). Check their website before visiting because new places are opening every week.

Watch this hilarious video of Irish comedians sampling Shenandoah Valley’s Route 11 potato chips.

— Shenandoah Vineyards

Shenandoah Vineyards, in Edinburg, is the second oldest Virginia winery. Not only is the wine really good but the views are magnificent.

— Pale Fire Brewing

Also on the Shenandoah Spirits trail is Pale Fire Brewing in Harrisonburg. Pale Fire has a classic music theme, so their brews have cool names like Lucille Oatmeal Stout and Major Tom IPA.

— Basic City Beer

The Shenandoah BeerWerks Trail includes only breweries and the list grows every week. Basic City Beer is in Waynesboro, which, co-owner Bart Lanham told us, won the title of cleanest water in Virginia. No wonder Miller Coors (definitely NOT a craft brewer) opened a plant nearby.

— Stable Craft Brewing

Also in Waynesboro, Stable Craft Brewing is owned and operated by an award-winning chef so the food might even be better than the beer (shhh, do not tell Chris, the brewmaster). The restaurant/draftroom are located in a magnificent repurposed stable and the grounds are gorgeous.

Visit five Shenandoah Valley wineries with local experts Shenandoah Wine Tours. Their $49 rate covers transport and a lunch, in addition to the five winery tasting. How fun!

4. Shenandoah Valley Scenic Roads

Shenandoah Valley can be driven through in a couple of hours on I-81, which many people consider the most scenic interstate highway in the United States. But, it is still just a highway, with belching trucks, lumbering snowbird RVs, and dazed-eyed drivers in a hurry to get nowhere. US Route 11 parallels I-81 through Shenandoah Valley, is a more fun alternative to the super highway, goes through most of the Shenandoah Valley commercial centers (mostly small towns), and even has a couple of drive-in theaters along it. Just off Route 11 in Mount Jackson, drive through the covered bridge on the way to the Route 11 Potato Chip factory.

During my recent nine days in Shenandoah Valley, we continually found ourselves on incredibly gorgeous small roads with hardly any other vehicles. Dozens of roads numbered in the 600s and 700s were super fun in my loaner Mazda Miata MX-5 (one week test drive) and later in our own McCool vehicle. Many wineries, farm stands, orchards, hiking trails, and attractions must be accessed from smaller roads.

5. Shakespeare in Shenandoah Valley

The American Shakespeare Center in Staunton, Virginia, gives audiences some of the pleasures that Elizabethan playgoers would have enjoyed during Shakespeare’s era. Its Blackfriar’s Playhouse is the world’s only re-creation of William Shakespeare’s indoor theatre. It is a special treat to attend a performance.

McCool Travel tip: try to buy a seat right on the stage and be part of the show. To visit or not to visit? VISIT! 

6. Edinburg Mill Museum

Being on the road, seeing museums nearly every day, I become jaded toward them. I was really impressed with the Edinburg Mill Museum. The historic mill was saved when most buildings were destroyed during the Civil War. Museum exhibits focus on the culture and history of the Shenandoah Valley, including transportation, agriculture, education, home life, military, and more.

I loved the collection of old American Red Cross posters.

7. Lee Chapel and Stonewall Jackson House

Sure, these two attractions in Lexington, Virginia focus on the most famous Southern generals of the US Civil War but I list them together because of the unexpected storylines they weave.

*** Spoiler alert. If you do not want to know those surprising storylines, skip the next paragraph and proceed to the next photo.

Lee Chapel is on the campus of Washington & Lee University. General Robert E. Lee is buried in the lower level, along with most of his family. The Lee Chapel museum focuses on the connection between Lee and George Washington, which surprises many people. Visit and learn more. The Stonewall Jackson House is the only place that focuses on the life of General Thomas J. Jackson prior to the Civil War. This was the only house Stonewall Jackson ever owned and the house tour focuses on Jackson’s work, civil, and family life up until the Civil War.

*** Spoiler alert complete!

8. Natural Bridge State Park

Allegedly explored by George Washington as part of his surveying work for Lord Fairfax, Natural Bridge was later owned by Thomas Jefferson and officially became a Virginia state park in October 2016. The natural stone arch is 215 feet high and supports US Route 11 which goes right across it.

Allow extra time to walk to the waterfall and visit the Monacan Indian Village.

Allow an extra hour to visit nearby Natural Bridge Caverns. Bring a sweatshirt because it is always 52 degrees underground; even when it is 95 degrees outside. McCool Travel tip: buy a combo ticket for both attractions and save $8.

Where to Stay in Shenandoah Valley VA

The George Washington, Winchester

Part of the Wyndham Grand collection, The George Washington Hotel Winchester VA is a relaxed luxury resort with a fabulous indoor pool and many other creature comforts. The property received the 2018 certificate of excellence from TripAdvisor and is located less than 75 miles from Washington DC.

The Inn at Vaucluse Spring, Stephens City

Located less than 15 miles from the above The George Washington Grand Hotel in Winchester is an absolute gem property. The Inn at Vaucluse Spring is a relaxed luxury B&B situated on 44 gorgeous acres in the northern section of Shenandoah Valley. If you have the opportunity, stay in the Mill House which might just be the best setting anywhere in Virginia.

Thank you for reading 8 Great Things to Do in Shenandoah Valley Virginia. Plan a road trip to the sites listed here with these guides from Fun in Fairfax VA :

Have you visited Shenandoah Valley? What other Shenandoah Valley places do you recommend?

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8 Great Things to Do in Shenandoah Valley Virginia was first published for McCool Travel on 1 November 2016.

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