Presented in partnership with Virginia Tourism. The opinions expressed here are entirely my own and the content has not been reviewed by the destination.

I’ve become a well-balanced traveler in my 40-ish years. I enjoy the big city life, smaller yet sill captivating mid-size cities and in the case of a handful of pockets of North Virginia, the quaint ones. I do, however, lean towards the mid-size ones, such as Alexandria and smaller ones, Winchester, as there’s a certain unmistakable charm to them.
Over a couple of days, my travelling companion, Nancy, and I discovered some shining gems on our travels that took us from below ground to a mountain crest and a few fun spots in between.

Fire up your favourite driving playlist, make sure your water bottle is full and snacks are packed as you embark on a fabulous road trip in this gorgeous part of the world.

Home Base: Tru by Hilton Winchester

Before any adventure starts, you’ve got to establish a home base and here, it was Tru by Hilton Winchester. Tru is their fun brand with a free hot breakfast, games in the lobby, the rooms are full of function with cool storage spaces and pet-friendly, and includes a local lobby mural.
I don’t usually get jazzed about hotels but this one is excellent. Add in free wifi and superb customer service with a very comfortable bed and it gets full marks from me.
It’s about an hour/90 km from Dulles using VA 7.

Walk This Way in Old Town Winchester

I’ll keep saying until there’s nobody left to listen; having a pedestrian-only part of a city/town is an excellent way to boost tourism and have locals enjoy their surroundings. They’re free to roam without the risk of an auto collision. Full marks to Old Town Winchester and their brick pathway, housing a marketplace older than 250 years, know officially as the Loudoun Street Pedestrian Mall. It’s even secured a place on the National Register of Historic Places Travel Itinerary.

There are shops galore, restaurants, entertainment and my personal favourite, a new cat cafe that opened in April called “Biscuits & Beans,” the best name I’ve heard of for these fine establishments. And yes, I went inside and admired these hopefully-soon-to-be-adopted kitties.

Biscuits and Beans Cat Cafe, Old Town Winchester, Virginia.

Even though part of my career is driven by 15 years of reviewing 100 new cars a year, having a this non-car zone is refreshing and gives you a different vantage point of the area.

Fantastic fries at the winchester tavern.

You’ll be hungry after racking up all those steps and I’ve got two options for you.
First, within the Mall is Winchester Tavern, down a few steps and into an ambient space with multiple dining areas. Only open for dinner, the burger and fries hit the spot and like the Tru, the service was splendid.

Fuego Tacos & Mezcal brings you marvellous Mexican fare in a jovial atmosphere, a mere one block away from the Mall. The Fajitas were as delicious as the menu described, as was the margarita and nachos.

Go Deep at Luray Caverns

Get in the car and head south for an hour to Luray Caverns, a majestic attraction that they’ve self-proclaimed as “Geology’s Hall of Fame.” When you go, you’ll see why it’s a fitting title.
This underground marvel features ceilings as high as 10 storeys, a mesmerizing maze of stone formations, draperies and my favourite, Dream Lake, a nearly optical illusion that can easily fill your camera roll.
The pathways are well lit with information plaques to help you learn about what you’re seeing.
This Registered Natural Landmark is enveloped with all formations being calcite, a crystalline form of limestone.

Remember to look behind you every few minutes for a different vantage point. As you move through this piece of living history, take your time as you realize that the formation of a stalactite takes 120 years to grow but a single one inch.
As a musician, I love this piece of information from their website: “The Great Stalacpipe Organ is the world’s largest musical instrument. It literally makes stalactites sing by gently tapping them throughout three acres of the caverns. It’s a musical masterpiece that can’t be found anywhere else in the world … or under it.”

Car & Carriage Caravan Museum at Luray Caverns.

Once you’ve emerged from the caverns, your ticket also grants you access to other on-site attractions, including the Car & Carriage Caravan Museum, Toy Town Junction, and the Shenandoah Heritage Village.

Small, Mighty and Meaty with Triple Crown BBQ

Across and oh-so slightly down the street from the caverns is home to one of the best BBQ joints I’ve been to. Ever. Triple Crown BBQ dishes out spectacular BBQ through family recipes flanked by fresh classic side dishes.
Owned by John and Joanne Coleman, they’re simmering in almost 20 years of award-winning BBQ, friendly service and they firmly believe in doing things right instead of rushed.
They’re seasonally based out of a food truck with picnic table seating on-site. The Sampler platter is where it’s at, along with their famous Crown sauce.

Lift Your Spirits on the Skyline Drive

skyline drive in shenandoah national park, virginia.

After spending a couple of hours underground, balance it out by doing one of the most delightful drives in the country.
Within Shenandoah National park is the famous Skyline Drive, a 169 kilometre/105 mile north south route that’s dotted with terrific twists and turns following the crest of the regal Blue Ridge Mountains.

Blue Ridge Mountains on the Skyline Drive Virginia.

As we were approaching from neighbouring Luray, our entry point was the Thornton Gap Entrance Station, approximately one third of the way down.
We opted to head south for Skyland, 18 km/11 miles from our entrance, then turn around and go to the top, being Front Royal Entrance Station. Our total distance would be approximately 68 km/42 miles of driving bliss.

Being in my 40’s, I grew up on paper maps and can handily read and navigate one. The one provided by the park is well laid out, with milk markers, overlook locations and elevations.
We stopped at a handful of lookouts and admired just how special these mountains and views are.

A quick nod to our road trip chariot, the 2026 Mazda CX-90, the largest vehicle they make. This three-row SUV drove more like a car than a mid-size. There was plenty of acceleration for the ascents, sharp handling and the ride quality was well-balanced. Throw in Mazda’s upscale, premium interior and the only Mazda I’d take over this would be the MX-5 roadster for this route. Ok, maybe the Mazda 3 because it comes in manual. Overall, the CX-90 is both a functional family hauler with a healthy does of fun behind the wheel.

Each twist and turn gave us something different to admire, a different perspective on where we were and you know I’ll be back to drive the entire of it sooner than later.
And yes, there are lookouts on both sides of the road.

Family Matters at Briedé Vineyards

While I’m not a wine drinker, Nancy is, which works out well because I’m a much better designated driver.
A short 10 minute drive from the Tru lands you at the family owned Briedé Vineyards, owned by Loretta and Paul Briedé. The walls are tastefully adorned with awards they’ve earned, the property is stunning and most importantly, we were treated like family, even though it was our first time visiting.
The winery was established in 2013 and their concept of a French-style boutique winery started to grow. Now, they have reds, whites, rosé, sparking and champagne for varieties of wines, there’s fresh-made food options and the atmosphere they’ve created is warm and welcoming.