A solo trip for the boozy books: Discover Virginia wine country in a weekend

No Napa? No problem. The Monticello Wine Trail is a nice option for us East Coast dwellers.

Published 10/13/2023 5:30 a.m. EDT

Barboursville Vineyards is on the Monticello Wine Trail in Virginia.

I was a road trip away from Napa Valley when I lived in California, but there was one problem: Like quite a few of my exes, my palate wasn’t mature yet. My evolution from sweet and bubbly to a dry, red wine lover didn’t happen until I moved back to the East Coast.

Nonetheless, I refuse to believe that Napa Valley is the only wine wonderland in the states worth experiencing. I’ve been to New York’s Finger Lakes and fell in love with Rieslings seemingly whisked together by the wine gods. When a co-worker mentioned Virginia’s own wine trails, I was intrigued.

I set my eyes on the Monticello Wine Trail, which is advertised as the “birthplace of American Wine” and has at least 40 wineries, which was plenty to choose from for a solo trip during the first weekend of fall.

Where I stayed

I booked an Airbnb in the lovely home of Kathy and Roy in Charlottesville, Virginia, which is three hours and change from Baltimore. I prefer Airbnbs over hotels because they’re more personal and usually affordable. A $50 Airbnb gift card I had went toward the $245 I paid for a two-night stay.

Many of the wineries were at least a 30-minute drive from the Airbnb, but coming in and out of the home was a breeze, and a comfortable couch and streaming services for when I needed a break from sipping and needed to recharge did the trick. The Airbnb is in a finished basement so I could hear footsteps above, but it was nothing overwhelming. The pitter-patters of a dog made me miss my two corgis. App superhosts Kathy and Roy also gave some amazing suggestions for breakfast, dinner and wine tasting.

Day 1: Gone with the wine

What I did

Pippin Hill Farm and Vineyards is a winery on Virginia's Monticello Wine Trail.

I couldn’t check into my Airbnb until 3 p.m., so I drove straight from Baltimore to my first winery, Pippin Hill Farm & Vineyards. A light search had proven this place Instagram worthy, and the scenery didn’t disappoint. On my drive up, the rolling hills looked like those intricate puzzles that take forever to put together but are so worth it in the end.

I recommend making a reservation if you go. The moment I arrived, a bridal shower group was strolling in taking photos by a path of flowers. It was the perfect day to be outside on the grassy lawn overlooking the vineyards.

I got a table inside, which was very rustic with light wood making up most of the interior and natural light flooding the dining area with a serene view of the mountains. I ordered the red wine flight ($20), which included Cabernet Franc, Red Pump, Cannon Red and Wild Common.

This flight influenced the rest of my trip. I’d never had Cabernet Franc before, but once I took a sip the wine lover in me wanted to do cartwheels. The taste was juicy like a plum and not too sweet, with a hint of black tea. The waitress told me it is a popular wine in the area, and I accepted the challenge of trying as many as I could throughout my trip.

What I ate

A red wine tasting flight and parmesan fries with herbs are just a few of the items on the menu at Pippin Hill Farm and Vineyards.

At Pippin Hill Farm and Vineyards, I kept it light and ordered hand-cut fries ($10) with parmesan and herbs. They proved to be a yummy and filling option. Eating was a top priority since those one- or two-ounce tasting pours can add up. By the time I got back to the Airbnb, the travel had caught up with me. I ordered in sushi from a local spot, put on snuggly socks and let Netflix take the wheel.

Day 2: When it rains, wine pours

What I did

McGuffey Art Center is a gallery in Charlottesville, Virginia housed in a former school.

The weather was cloudy and rainy Saturday. I had an early-morning start, and many of the wineries didn’t open until after 11 a.m. To kill time, I went to McGuffey Art Center, a gallery housed in a former school built in 1916. Some of the classrooms are now artists’ studios. I’m a big thrifter, so I also headed to Twice Is Nice, a local resale boutique, and found a forest green Talbots coat advertised for over $300 online. I paid $28 for it.

My first winery stop was Eastwood Farm and Winery for a simple reason. It was raining, and Eastwood was one of the first to pop up when I searched wineries with indoor seating. I got there just as a band called Cake Fight started covering songs such as “Kiss Me” by Sixpence None the Richer and “Colors” by Black Pumas. I had the Red Reserve Tasting ($18) with Merlot, Cabernet Franc, Meritage and Petit Verdot. Though I ended up still liking the glass of Cabernet Franc best, the Petit Verdot was a close second with floral notes and a jam-like, black cherry finish.

Eastwood Farm and Winery is tucked away along the Monticello Wine Trail.

The next winery, Blenheim Vineyards, can only be described as a cool, cone-shaped clubhouse. It’s a very intimate setting with glass portions along the floor so you can see the wine processors at work below. And the best part? People could have their dogs inside! I met an adorable mini goldendoodle named Mango who was the perfect pairing for yet another red wine flight ($15).

Blenheim Vineyards sits on the Monticello Wine Trail with portions of glass in the floorboards to view the winemaking  process.
Mango, the mini Goldendoodle, eagerly approached guests at the Blenheim Vineyards in Virginia.

Where I ate

For breakfast, Kathy and Roy highly recommended Farm Bell Kitchen in Charlottesville’s downtown area. I can get very hangry and impatient in the morning, so I made an 8:45 a.m. reservation. I’d highly recommend booking ahead of time; even during the rainy period people still shuffled in back to back. I ordered the smoked salmon on baguette pieces with bruschetta ($13). Lox is love in my book, so I couldn’t turn it down. I also had brioche French toast with berries and maple syrup ($16) and a side of bacon ($5), which was my favorite part of the meal. I topped the lovely meal off with a mimosa ($7) because wine not?

Farm Bell Kitchen in Charlottesville, Virginia serves brioche French toast with maple syrup and berries.

By nightfall, I was in the mood for Italian and moseyed into downtown again against the wind and rain. I found a small spot called Sal’s Caffe Italia and ordered a grilled chicken and sun-dried tomato pasta dish called the Gianluca ($26), which I pointed to on the menu instead of attempting to pronounce to spare embarrassment. The waiter was very kind and easily explained how to say it. I also ordered mozzarella sticks ($13) and a carafe of red wine ($21). The pasta needed a little extra love (salt and pepper), but it was a quick fix.

Day 3: Sip back and enjoy the views

What I did

The Barboursville Ruins is a structure designed by Thomas Jefferson that was destroyed by a fire in 1884.

I inadvertently saved my two favorite spots from the trip for last. Barboursville Vineyards, another splendid suggestion from Kathy and Roy, was about 30 minutes from my Airbnb and on the way home. The scenery was absolutely beautiful with warm, roasted orange and red color schemes indoors that were so calming and fitting for the first days of fall.

I did a tasting in Library 1821, a section of the winery that houses some of its older vintages. I had the classic flight ($25), but I adore red blends and it is known for one called the Octagon, so I added it as one of my tastings. I couldn’t quite put my finger on the distinct tastes of the 40th-anniversary edition the server let me try, but it exploded with flavor.

The vineyard is also home to historic ruins: a structure designed by Thomas Jefferson for Gov. James Barbour in 1814 and destroyed by a fire in 1884. I ordered a half glass of the Cabernet Franc (yes, it’s my favorite now) and walked to the site, passing a field of wildflowers still trying to find the last days of summer.

The Barn at 678 Vineyard in Virginia has a greenhouse seating option with flowers and picnic tables.

When I left Barboursville, I found another winery, the Barn at 678. The different settings for sipping drew me in. I got a flight of four wines ($16) – Chardonnay, Cabernet Franc, Reserve Red and Petit Verdot – and enjoyed them in a majestic greenhouse surrounded by flowers and picnic tables. Oh, and the music from the greenhouse speakers was an awesome touch to ensure a laid-back vibe. There were also seats around a couple of fire pits and other covered sectional seats adjacent to hammocks. I enjoyed the crisp Chardonnay, and the Cabernet Franc was another certified winner.

What I ate

Library 1821 has a cheese and meat charcuterie tray option to pair with their selections of wine. The goat cheese is a must try.

Kathy and Roy’s oatmeal in the Airbnb had me covered for breakfast, but I couldn’t end my trip without a charcuterie board, so I ordered a small tray of cheese from Barboursville Vineyards ($20). If you take nothing else from this article, I am telling you to order the cheese board and eat the goat cheese with olive oil, salt and pepper. Let it change your life.

Flying solo to a new place can be nerve-wracking, but a slightly anti-itinerary trip to Virginia’s wine country is doable and worth a try. Cab Francs now make my wine-loving world go around, and I can’t wait to go back and try the places I missed.

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