I’ve lived in eastern Pennsylvania for the past 20 years, but I grew up in a small town in southwestern Virginia that is located along the I-81 corridor just south of Roanoke. A few times a year, we travel across the PA Turnpike and down I-81 through the lush Shenandoah Valley to visit my family. Every time we travel that route, we drive right past Winchester, Virginia, but we never stopped for more than a quick bite to eat or a gasoline fill-up.
I recently had an opportunity to explore this area of the Shenandoah Valley and its living history, thanks to a partnership with family travel site Trekaroo and Go Blue Ridge. We are one of five families that were invited to experience the Shenandoah and Piedmont Valleys and report back, plus we are giving away a family vacation at the Massanutten Resort!! Stay tuned for more information on that at the end of this post.
Many of you followed along on our adventure via Facebook and Instagram, but I’ve finally had time to sort through all of my photos and put my thoughts together, and I’m excited to share them with you.
Until this trip, I had no idea that Winchester holds such historical significance for our country. While we were there, we learned that Winchester was the training ground for George Washington during the French and Indian War as well as a location for prisoners during the Revolutionary War. But Winchester was also a strategic prize in the Civil War, changing hands some 70 times during those four years. There are several historic sites related to both wars that you can tour, and many of the buildings in town have fascinating stories to tell. The area also offers a variety of outdoor adventures, amusement parks, children’s museums, farm experiences, and underground caverns to explore.
Go Blue Ridge Travel and their Shenandoah Kids Trail website is a wealth of information for families traveling to the area. Bucket is their friendly little mascot and tour guide, helping you make your bucket list for visiting the region.
They left a flat Bucket in our hotel room so we could incorporate him into our adventures. My 9-year-old daughter, R, took ownership of him and took him with us on our adventures.
If you go to the Shenandoah Kids Trail website, you can search for things to do by region or activity type. It’s very well organized, and the information is robust. This is a great resource for families traveling to the region, and I would highly recommend using it as a guide if you ever visit the area.
If you ever visit Winchester or find yourself passing through, here are some fun family-friendly things to do.
Things to Do with Kids in the Shenandoah Valley
1. Go to a Drive-In Movie
My kids experienced their first drive-in movie at the Family Drive-In Theater in Stephen’s City, which is just a few miles outside of Winchester. Everyone had a blast. It was just good, old-fashioned fun. They loved that they could enjoy the movie from the car, but they were still able to get out and walk around if they got antsy. It was nice to be able to move around, and by the end, half of us were asleep, but that was half the fun.
You have the option of listening to the movie through your radio (with the air conditioning on) or through a speaker that you set inside your window. I also appreciated that they had smoking and non-smoking rows. There were drinks, snacks and candy for purchase.
The owner came out and greeted us, and everyone was friendly and happy to be there. It is a great way to spend a spring weekend evening.
2. Visit Stonewall Jackson’s Headquarters
Because we toured his home in Lexington, Virginia last spring, our family was eager to visit Stonewall Jackson’s house in Winchester that he used as his headquarters during the winter of 1861-1862.
It was the last place he stayed with his wife before he suffered an untimely death at the prime of his career due to friendly fire. While this wasn’t his primary home, it contains the largest collection of Jackson memorabilia and personal objects from members of his staff.
The tour guides were knowledgable and engaging. They were able to bring the presentation down to the level of our children (ages 9, 12 and 15) without sacrificing content. At the end, we had a chance to peruse their small gift shop, which had a great selection of books and mementos of the Civil War. If you’re an American history buff, this is an attraction you don’t want to miss.
3. Explore the Old Town Winchester Walking Mall
With its shops, restaurants, and seasonal farmer’s market, this is a great little area of town to explore. We happened to be there the weekend of their KidzFest, so there were all kinds of fun activities for kids, such as face painting, balloon animals, water slides, and more.
This isn’t the kind of event I’d go out of my way for, but if I was a local, I’d definitely pay a visit. That said, the Walking Mall would be fun at any time of year, KidzFest or not. There were several cute shops, some nice looking restaurants, an ice cream shop that comes highly recommended, and it’s a pretty area to explore.
There were several cute shops in Winchester, but my favorite was Flavor Pourfection — an artisan oil and vinegar tap room. I KNOW!!! Who even knew there was such a thing!??
We tasted a few of the olive oils and brought a bottle home as a thank you to a friend for watching our fur baby while we were gone.
4. Tour the Museum of the Shenandoah Valley
On the last day of our trip, we spent a few hours at this scenic museum and the Glen Burnie House located on its property. We enjoyed perusing the artwork, touring the historic house, and exploring the picturesque gardens.
The Glen Burnie House was owned by the Wood and Glass families since the 1700s, and it’s furnished with a remarkable private collection of decorative arts. We enjoyed exploring these collections, and I appreciated how they encouraged us to touch and enjoy the pieces. It felt more like we were visiting a home than touring a museum.
While we could only tour the first floor of the house, we enjoyed studying the fully furnished miniature model of the Glen Burnie house that is on display in the dining room, providing visitors with an exact look at how the house was furnished as a private residence.
Beyond the house, six acres of formal gardens beckon, including the Pink Pavilion and Fountain Courtyard that are frequently used for entertaining.
The tour is self guided, and my kids enjoyed carrying their walkie-talkies and listening to the commentary along the way. The property was undergoing renovations when we were there, so it wasn’t the ideal time to tour the grounds, but we enjoyed our visit and would definitely recommend visiting if you are ever in the area, especially if you enjoy touring historic homes.
5. Visit historic Fort Loudoun
Fort Loudoun was the site of Washington’s regimental headquarters during the French and Indian War, and we were in Winchester on the morning of their Fort Loudon Day, an event that commemorates the start of building Fort Loudoun in May 1756. This year, a living history interpreter of the 18th century colonial frontier dressed in backwoodsman attire presented a first person account of life on the ‘American’ frontier in the years 1754 to 1775.
We happened along towards the end of his presentation, but we listened for a while, until we were distracted by the revolutionary war reenactors rehearsing their march into town. The kids got quite a kick out of that.
Tours of the property are available. Find out more at FIWF.org.
6. Take a Historical Cemetery Tour
This is another thing we wanted to do, but we ran out of time. This tour takes you on a journey through two historical cemeteries tucked away in the beautiful Shenandoah Valley, Winchester National Cemetery and Stonewall Cemetery.
7. Visit the Shenandoah Valley Discovery Museum
This is a 4-floor children’s museum that boasts a variety of interactive and hands on exhibits that focus on science, mathematics, humanities, and the arts. I heard great things from Perry (see below) and it was highly recommended by Blue Ridge Travel. We hope to stop in sometime when we are passing by Winchester on a trip to Roanoke.
8. Eat at Just Like Grandma’s (a.k.a. Perry’s)
We found this restaurant on our own, and we are so glad we went. It looks your typical hole-in-the-wall with a single counter running the length of the restaurant, but the food and service is anything BUT hole-in-the-wall. The owner, Perry, does all the cooking right in front of you. He’s also a wealth of information, and he was really sweet with our kids.
The food was A-MAZING. He shredded a whole potato and dropped it into the deep fryer for our hashbrowns, broke fresh eggs into a bowl for our omelets, and made my 12-year-old daughter (who dislikes traditional American breakfast foods) fried chicken and french fries at 10am. Oh, and the sausage? To. Die. For. Do NOT come to Winchester without visiting Perry’s. This will now and forever more be our breakfast stop when we travel from Roanoke to Philly.
As for our accommodations, we stayed at the Wingate by Wyndham in Winchester. It is conveniently located right off of I-81. Everything was clean, the staff was friendly and accommodating, and a continental breakfast is included with an overnight stay. They provided us with a cot since we are a family of five, which worked out fine. This was our first experience with a Wingate hotel, and we will definitely consider them for our future travels.
Winchester is about three hours from Philadelphia and less than two hours from Washington D.C. or Baltimore. The area offers a wealth of historical sites as well as outdoor adventure activities, museums, and amusement parks to explore. For more information, be sure to check out Shenandoah Kids Trail.
WIN a Family Vacation!!
Enter to win a family vacation at the Massanutten Resort! This vacation includes a 5-night trip (6 days) in a 2-bedroom condo at the luxurious Massanutten Resort in McGaheysville, Virginia, along with 4 Indoor/Outdoor WaterPark tickets and a $50 Resort Gift Card. That’s a $1682 value! Someone is in for a very good time!! Enter to win on the Trekaroo website. Good luck!!
Disclosure: I received a complimentary stay at the Wingate Hotel via Go Blue Ridge, and some of our activities in the region were comped in order to facilitate this post. The opinions stated are my own. This is a sponsored post for the Trekaroo Influencer Network.