Virginia is for Lovers of Road Trips

Published May 31st, 2024

Virginia is for lovers and there’s a lot to love here from Charlottesville to Wytheville and plenty in between. From divine driving routes, history, small town charm, traditions, excitement, creativity and more, these parts of Virginia need to be on your experience list. 
For this road trip that started in Toronto, the 2024 MINI Cooper JCW was our chariot. Yes, it’s a small vehicle with a long legacy of exciting driving dynamics but this was a special model; it’s the last manual transmission model for the MINI Cooper.

We loved every moment of our overall mileage of 2,683 km (1,667 miles) and as we kicked the clutch and rowed our own gears, it was certainly the right vehicle for this Virginia road trip. 
Our trip was anchored around the Back of the Dragon and we spent time in Charlottesville, Floyd and Wytheville as well.
Whether you use this as a map, guide or inspiration, this is a trip that we’d absolutely do over again at least a few more times. 
Buckle up, put your favourite road trip tunes on and come along for a drive!

Charlottesvillle

Ix Art Park & The Looking Glass


As a prominent community hub in Charlottesville, the Ix Art Park is an exquisite public space overflowing with creativity. Enveloped in murals and art installations, it’s also the home to festivals, events, workshops and the seasonal Saturday Farmer’s Market.
Their mission is “to spark creativity and inspiration in people’s everyday lives.”
Impressively, this year-round attraction is Virginia’s first permanent immersive art experience. 
Within Ix is The Looking Glass, a spectacular space created by dozens of local artists. The first portion is a collection of installations and vibrant colours that’ll dazzle you along every step. The second half is a space that enables your creativity with hands-on opportunities to exercise your creative side through creation.


Charlottesville Historic Downtown Pedestrian Mall

After experiencing hundreds of cities throughout my travels, having a pedestrian-only space is something every city should have. I’m not anti-car. Rather, I’m pro-community and smart use of public space. Boasting over 120 shops and an excess of 30 dining options within historic buildings that have been modernized, there is a trolley service here and a plethora of parking options surrounding the Charlottesville Pedestrian Mall. 
The Bebedero is an outstanding authentic Mexican restaurant that features occasional live music and Revolutionary Soup serves up stellar soup, sandwiches and snacks. Whether you’re strolling through or spending time here enjoying the additional entertainment options, this is a blueprint of how to design a pedestrian space in a bustling urban environment.

Thomas Jefferson’s Monticello

This World Heritage Site that’s minutes from downtown Charlottesville, was the home to the third president of the United States and is a living piece of history. Adorned with historical artifacts from Jefferson’s life, including hundreds of books, trinkets and more, this gives you a look into his life and who he was. 
Through transparency, Monticello does not hide that this was once a plantation with enslaved people, which is a smart approach because despite all of the influential aspects of his life (authoring the Declaration of Independence, the Statue of Virginia for Religious Freedom and founding the University of Virginia) there are still parts of history that should not be overlooked. 
Enjoy a guided or self-guided tour and learn more about the life and times of this polarizing character.

Michie Tavern

Down the hill from Monticello is where you’ll find splendid Southern food through a bountiful buffet. Fried chicken, buttermilk biscuits, BBQ pork and much more are on the menu, all wrapped in an 18th-century style pub. Interestingly, it was initially located 17 miles away and once bought in 1927 by Josephine Henderson, she moved it to its current location to where it is today and capitalizing on the people visiting Monticello. The food is fantastic and story is superb - definitely find time to get here.

Jefferson Vineyards


Also in close proximity to Monticello is Jefferson Vineyards, complete with 400 acres of vines. Some say Jefferson was America’s original wine expert given his time living in France. Regardless, this vineyard produces a variety of wines, with Chris Ritzcovan at the helm as winemaker for 11 years. Come for a tasting, stay for the views and relaxed vibes.

Carter Mountain Orchard


Take a 10 minute upward scenic drive from the vineyard to see panoramic views at Carter Mountain Orchard. Yes, the fresh apples, baked goods, gift shop and winery are quite good but it’s the vibrant views here that provide a wonderful backdrop as you enjoy everything apples here. 



Set your home base at The Quirk Hotel in the heart of the city. This upscale yet approachable hotel offers well-appointed rooms, a large lobby, an on-site art gallery and during warmer months, head to their rooftop patio for food, drinks and of course, the views. If you’re interested in a bit of artsy flair in a modern setting for your hotel, this is it. 


Floyd


2.5 hours southwest of Charlottesville brings you to Floyd, which has a quaint and charming feel to it. Make your way to the Floyd Country Store on a Friday night for what adds an exclamation point to this small town. Celebrating 40 years this year, the Friday Night Jamboree is an event everyone should experience at least once. The community comes together, including some from out of town, to be entertained and dance the night away by talented musicians that play bluegrass, gospel and old-time music. This long-standing tradition brings together people of all ages, serves delicious food and has an unmistakeable energy. 
Plus, the community is mighty friendly, welcoming both Steph and I with open arms and making us feel immediately at home. 
Rest and recharge at the nearby Floyd Hotel, which offers clean rooms, great service and a pretty good breakfast.

Back of the Dragon


100 miles west of Floyd and a bit over 200 miles from Charlottesville is the famed Back of the Dragon drive route, complete with 438 curves twisted over 32 miles of sheer driving joy. 
I’ve driven through California and British Columbia’s mountains. I’ve driven wonderful winding east coast Canada routes. This roaring dragon is right up there and in fact, is now one of my top five driving routes ever. As someone who’s driven over 1 million kilometres and is professional automotive reviewer, this is spectacular. 
Driving the last manual MINI Cooper performance edition was absolutely the right car for this experience. It’s got outstanding handling, ample power and handled everything the Back of the Dragon threw at it with ease and precision. My rating is a solid 78/10.


Before driving the route in southwest Virginia going from Marion to Tazewell, start at the Visitors Centre and grab some food and drink before you set off. Once on the road, it’s crucial to be safe and smart as you navigate the twists and turns. There are a few places with pull-offs to enjoy the views but while you’re in motion, please be careful. 
We did the route three times; that’s how much of an impact it had. It takes around 50 minutes to do the entire route one-way without stopping and moving at a safe, moderate pace.

Wytheville 


Interestingly, there’s only one Wytheville in the world and here it is! Located at Interstate’s 77 and 81 in the Blue Ridge Mountains, chances are you’ve been through it if you’ve taken road trips in this part of the world.

Big Walker Lookout

There’s quite a bit happening here for its small footprint. 
Starting with the 100 foot high observation tower, on a clear day you can see five different states, which are Virginia, West Virginia, Kentucky, Tennessee, and North Carolina. The views at the top are wonderful so make sure you’re smartphone has some juice in it to capture video and photos. Once you’re back down, visit the BW Country Store which has all sorts of trinkets, souvenirs, food, drink and most importantly, a history of the area and the tower.

West Wind Winery

Prioritizing small-batch wines, this fourth-generation homestead is worth visiting. 
They offer a selection of red, white and sweet wines from Riesling to Cabernet Sauvignon to Galena Creek Blackberry and more. 
The store is cute and spacious, with knick-knacks galore, plus plenty of wine to take home.
Come for the sampling, stay for the welcoming atmosphere.

New River State Park & The Inn at Foster Falls


If you enjoy being outdoors, definitely get here and enjoy all of its goodness. Starting with the New River, which is one of the oldest in the world and as a rarity, flows south to north, this nearly 100 km long river is flanked by over 60 km of trails. Enjoy the rail trails by walking, hiking or biking and know that these were donated by Norfolk & Southern Railway nearly 40 years ago.

The Inn at Foster Falls is the only hotel amongst all Virginia State Parks. Built in 1886 for the mining community and then a girls school, then orphanage before it lay empty for 50 years.
In 2023, it reopened as a unique hotel with 10 boutique rooms.
Enjoy easy access to the trails, water, impressive dining in a truly special space.

Log House 1776


It’s primarily a restaurant but it’s also a destination. With all sorts of nooks and crannies to be seated at, plus traditional large dining rooms, each visit can be a cool experience here. Food-wise, there’s a decent selection (much better than a menu that has over 10 pages!) and traditional American food is on the menu. 
This special place for both locals and tourists boasts a delightful garden to stroll through, plus two gift shops with all sorts of this and that, with something guaranteed to strike your fancy.

Trinke Mansion Bed & Breakfast

Previously earning one of the 10 best B&B’s in America, Trinkle Mansion is utterly enchanting. From its majestic stance, historically decorated and cozy rooms, to various sitting rooms on the main floor, I can easily see the strong appeal here. Owned by a wonderful couple, Patti and Bernie since 2007, this over 100 year old house exudes charm throughout. Oh, and the breakfasts is an experience showcasing the height of southern hospitality.