48 State U.S. Road Trip – Exploring Kentucky, West Virginia & Virginia

48 State U.S. Road Trip – Exploring Kentucky, West Virginia & Virginia

It was hard to leave Nashville but there were so many other places to explore on my solo 48 state road trip. So, I headed North to Kentucky [state 18 out of 48!].

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises!

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Not having an itinerary made exploring Kentucky, West Virginia & Virginia an extra great time! I was headed to meet my oldest bestie in Maryland but had a couple of days to check out the sites.

The late evening drive up Kentucky made for some pretty visual entertainment. There were gorgeous sunset colored clouds filling the sky and those illuminated rear-ended bugs showering my windshield with their glowing carcasses.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Not only that but, upon arriving in Lexington, their ball field put on a firework display that put the 4th of July one in Alabama nights earlier to shame! My eyeballs were quite regaled.

I located a spot to park/sleep and the next morning went exploring. Kentucky is full of big fancy mansions! The old-school colonial style that sit on large plots of land. It was so fun driving up and down the tree lined residential streets admiring these beautiful homes.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Horses are definitely the main theme in this state but coming in close second is bourbon. Scrumptious Kentucky bourbon.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

As a red wine lover, I could go wine tasting for days but never have I gone bourbon tasting. Luckily, they have a bourbon trail that leads to all the distilleries so that I may check this off my list. Now only if Priscilla (my Prius) could drive herself. (just kidding they offer plenty of transport options in this area just for this reason)

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

The next day, and yes completely sober from Kentucky bourbon, I headed to West Virginia [my 19th state].

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Historic buildings lined the river’s edge and wound their way through the downtown distracting me from the proper bridge entrances/exits. So, I basically got to see the downtown quite a few times throughout this capital city, Charleston.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Due to this I did discover an amazing bakery with fresh Parmesan sourdough loaves. The Charleston Bread Company was delicious! I may or may not have eaten every crumb. #NomNomNom

Grabbing some breakfast and wandering around the downtown streets was lovely. This small state was a lot cuter than expected.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

Before I knew it, I was in Virginia [State #20!] and headed to Shenandoah National Park. I heard it was a beautiful park and couldn’t wait to explore it! Here are some must-dos while exploring Virginia:

I was delighted to find that Kentucky, West Virginia AND Virginia were full of fun & lovely surprises! Here's why all 3 should be a part of your next road trip.

While driving the windy road that my GPS instructed me to take [again it is a British male voice (I call him Watson) so I unfortunately blindly trust what he says because I LOVE his accent] I passed a couple of winery signs. Then there were more. I felt it was my duty to investigate further.

Thanks for leading me here Watson…this is why I trust you! 😀

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

1. Go Wine Tasting in Virginia

I am fascinated by the grape growing/wine making process and am that girl that asks five million questions whenever I get the opportunity to visit a vineyard. All vineyard owners provide me with the same advice when I confess that it would be a dream to own one someday:

“Want to make a million dollars by starting a winery? Then start with two million!” Lol. Noted.

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

Although I love the bold reds, the humid region of Virginia can’t quite grow that varietal, but there were some tasty options regardless. It constantly reminded me of Cambria, Templeton and Paso Robles in California that I frequent often. Beautiful green hills, small tree lined back roads, and friendly people out and about tasting Virginia wine just because it is so much fun.

I met some awesome people who provided fabulous referrals and even ran into a couple WWOOFers (World Wide Opportunities on Organic Farms). I secretly want to be a farmer someday so this organization has always been on my list of things to do.

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

Each country has their own database and you can provide manual labor (farming/gardening/animal care and more) in exchange for room & board on farms across the globe. It’s a great way to explore the countrysides of foreign lands while spending next to no money.

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

Make sure to check out Grace Estate Winery [the beautiful panoramic views above were shot there] and Stinson Vineyards.

2. Explore Charlottesville 

I wrapped up my endless question asking and made my way to Charlottlesville. Oh Charlottlesville. It is so sad to think that I could have completely missed this adorable town if a local had not steered me in this direction.

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

I searched for parking but found everything quite full. A long line of people stretched through the main walking path and I discovered it was due to a Sara Bareilles concert that evening.

Oh that would be fun…she has an amazing voice, I thought. So I continued walking and googling the cost for tickets when I made it to the Spanish Tapas place, Mas, that was recommended in Historic Downtown Belmont. OMG. Amaze!!!

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

I decided a concert ticket was not in my budget but I would wander back thataway and just see if any other options presented themselves. As I approached the venue, I spotted a bridge behind the stage. There was a small row of locals sitting along side a small row of very intoxicated homeless dudes.

It seriously was the best seat in the house!

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

Not only were we closer to the stage than the front row inside, but the locals and homeless were friendly and entertaining respectively. I meet some great people and got even more referrals. And thus, my decision to stay the night was made.

Sara put on a fabulous show…I highly recommend partaking in one of her concerts.

4. Go To A Polo Match

The next morning I visited a winery that has polo matches on Sundays. Impromptu wine AND polo?! My kind of day!

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

It was such a treat! The wine was delicious and polo match was so fun to watch. It was my very first divot stomping! Nikalus (my paparazzi-like camera lens) was so pleased I was finally putting his ridiculous zooming skills to proper use.

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

 I may or may not have located the area where the riders change. #dontjudge #hottiepoloplayers

I was delighted to find out how awesome Virginia was while driving through on my solo 48 state road trip

Overall, Virginia IS for lovers but even when solo…you will fall in love with this very lovely state and it’s neighbors Kentucky & West Virginia!

AHC Shout Outs: To the super sweet Mariko! Thanks for sharing your awesome town with me! [& for the fabulous referrals]

Thanks for reading! Have any favorite spots in Kentucky, West Virginia and/or Virginia? Thinking of road tripping there? I’d love to hear from you in the comments below. 😀

P.S. Read about Amy’s solo 48 state road trip [on a small budget] here

My solo 48 state road trip route - I can't recommend more that you explore as many states as possible! :D

Amy’s 48 state road trip route [starting @ home = Southern California] to: Arizona, New Mexico, Colorado, Wyoming, Nebraska, Kansas, Oklahoma, Texas, Arkansas, Louisiana, Mississippi, Alabama, Florida, Georgia, South Carolina, North Carolina, Tennessee, Kentucky, West Virginia, Virginia, Washington DC, Maryland, Delaware, Pennsylvania, New Jersey, New York, Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire, Vermont, Ohio, Indiana, Michigan, Missouri, Illinois, Iowa, Wisconsin, Minnesota, South Dakota, North Dakota, Montana, Wyoming [again], Idaho, Oregon, Washington, California, Nevada & UTAH!

Use these handy links to save on your next trip to Virginia:

Exploring Virginia and it's awesome wineries is such a lovely experience that you need to try stat!

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