Things to do around Shenandoah National Park

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Things to do around Shenandoah National Park

If you live in the south it is not unusual to feel extremely jealous of the northeast’s fall foliage colors and the adorable towns that are enveloped therein. However, on an impromptu road trip through Shenandoah National Park with a dear friend I was able to find an abundance of activities and autumn colors in some of the southern states, namely Virginia. This is a list of only a few, of many, things to see and do.

Travel Tip: The best driving route is from south to north so that while driving the sun is not directly in your eyes. I learned this lesson the hard way. Following is my specific itinerary which ran north to south. Feel free to modify this plan; start by reversing the route!

Winchester, VA

Thinks to do around Winchester, VA

Start your Shenandoah National Park fall foilage journey in Winchester.

f you have the time, stop by this community and walk around the downtown mall.  Check out the Stonewall Jackson’s Headquarters Museum. The building showcases memorabilia from the Civil War.


We had dinner at Village Square Restaurant, which is aptly named. The food was delicious, and the seasonal drinks were perfect for a crisp fall night.

Restaurant in Winchester, VA

Shenandoah National Park, VA

Discover nature's symphony at Shenandoah National Park, VA

A road trip through Virginia during the fall would not be complete without driving through the Shenandoah National Park. Start at either the southern or northern entrance station; to keep things moving along it is best to purchase your passes online before arrival. 

Skyline Drive, the main road through the park, can get very crowded during the weekend, so if you have the availability, chose a weekday to avoid the crowd. We visited on a Wednesday and encountered very few vehicles. This made sudden stopping for photo ops much easier!

Shenandoah National Park, VA

A stop at the Dark Hollow Falls turnoff cannot be forgotten!  Do not forget to pack appropriate footwear for a mere 1.4-mile roundtrip trek.  The descent is steep and somewhat arduous with slippery rocks and rough terrain.

Shenandoah National Park, VA

Upon your arrival, you will be rewarded with a stunning and picturesque waterfall. Take it all in and enjoy every bit of what nature has to offer.  You will need fond memories to recall as you conquer your approximate 3-tenths of a mile ascent return. Be sure to have electrolytes staged in your vehicle for refueling!

If you are traveling during the fall months, an updated foliage map can be found on the Shenandoah National Park Service website.

Shenandoah National Park, VA

Fun Facts

  • While no one knows for sure how the park received its name, it is believed that it could have been called Shenandoah after the fallen chief Sherando.  Or, possibly for the Indian tribe Senedoes, who called the valley home until 1730.
  • If you are an avid hiker, try your hand at the Appalachian Trail that clocks in around 100 miles.
  • Overlooks and stops were named for various reasons. For example, some of the points were named after the families that once lived there. Others were named for their purpose, such as Limberlost Trail which crosses through a forest that was saved from logging by Addie Nairn who paid $10 for each old-growth hemlock tree. The hemlocks were later destroyed by insects and replaced with beautiful laurels. Additional trails are named after rock formations, such as Chimney Rock, and animals or plants that occupy the park. In the case of Mary’s Rock, a legend states that a girl named Mary climbed up the mountain when she was young and returned with a bear cub. Other theories include that it was named after the wife of William Randolph Barbee, or that she married Francis Thornton and he brought her up on the cliff to show her the land that they would eventually own together. No one is sure of the name’s origin, but there is a 670-foot tunnel with her name on it.
Shenandoah National Park, VA

Other Things to do around Shenandoah

Showalter Orchard

(exit Shenandoah National Park to visit)

Other Things to do around Shenandoah

About 45 minutes outside of the Shenandoah National Park there lies a beautiful orchard, inn, and cider mill.

The farm was started in 1965 when Joe Showalter established a fresh market for local residents. In 1975 the cider press was added to repurpose the blemished apples into cider. Grab a bottle while you are on the property.

Other Things to do around Shenandoah Shenandoah National Park, VA

We had a wonderful time picking four different types of apples around the beautiful property and enjoying the surrounding views. Peaches are also available to pick in season.  

If wandering around picking your own fruit is not your idea of a good time, no problem!  Grab the already selected produce from their store.

Other Things to do around Shenandoah Shenandoah National Park, VA
L.L. Bean boots make the best apple picking shoes!!!

This is such a gorgeous property that you may consider staying overnight. The wonderful old cider house offers guests an updated and comfortable stay with access to the cider house kitchen that is fully stocked with all of your cooking or baking needs.

Other Things to do around Shenandoah Shenandoah National Park, VA

Make sure to arrive in time to take part in the cider tasting. The website will provide updated hours of operation.

Cider Mills and Vineyards

What could be better during a fall road trip than wine, mead, and cider tastings? Here are just a few, of the many, options available in the area.

Cider Mills and Vineyards

Other Amazing Mills and Vineyards:


          234 Vineyard Lane, Afton, VA 22920


          5022 Plank Road, North Garden, VA 22959


          2800 Berry Hill Road, Nellysford, VA 22958


          1020 Rockfish Valley Hwy, Nellysford, VA 22958


          200 Mosbys Run, Roseland, VA 22967


Other Things to do around Shenandoah Shenandoah National Park

Worth a stop before or after your drive

Truharvest Farms is a stop for all things hemp and pumpkin picking in Christiansted. I stumbled on to this during a drive on the interstate.

Other Things to do around Shenandoah Shenandoah National Park, VA

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