The New Kid on the Block

Published by Ramble Virginia
A Limo Company’s Guide to Exploring Virginia

Much like the fabled Groundhog of Lore, aka “Punxsutawney Phil,” I have finally emerged from my long winter slumber. After months of actively avoiding the glacial cold, bitter winds, and surging covid cases, I am venturing back out on the Monticello Wine Trail. My first stop is to the New Kid on the Block, and the closest to Downtown Charlottesville, Eastwood Farm and Winery. I did not get to meet the owner, Athena Eastwood, but I was able to connect with the Outdoor Tasting Room Manager, Diana Nelson. It was much different from my previous interviews with owners and founders of the other establishments that I have visited, but in a completely amazing way that I didn’t realize until after our conversation.

When sitting down with an owner of a winery or brewery, they are talking about their creating – their child – to me – an utter and complete stranger. As someone with a 7-year-old son, I can certainly say that I could not imagine telling some random person what a terror he can be at times. Do not get me wrong. I love my son more than anything in the world and he is not a bad kid or unruly, far from it actually. My wife and I have worked very hard to teach him about right and wrong, to say please and thank you, and, in general, to not be a jerk, but he does have his moments where I wonder about his prospects of actually making it to adulthood without severe bodily injury, either to himself or us. I would not expect a parent to tell me all of the bad stuff about their kid, only to sing their praises. So, getting to sit down with an employee and hear their view of the winery was unexpected and refreshing. After listening to Diana about Athena Eastwood and the Farm itself, I can tell you that they are raising the kid right.

And so, without further gilding the lily and with no more ado, I give you the first Ramble of 2021!

Okay. I lied. Just a touch more ado. Shout out to Paul Bettany as Geoffrey Chaucer before he was Vision. His performance is how I like to imagine Chaucer was in my head. Now that that is out of the way…on to the Ramble!


When arriving at Eastwood Farm and Winery, you will notice their sign shows a Blue Boar clenching a branch within its jaws. Stylistically, it feels very old world European, and, for lack of a better phrase, it looks good, at least to me. However, I felt that there was more going on with this imagery than just artistic design.

I knew that the Boar has long been a symbol of hospitality, but I decided to do a little further digging into this symbol. Historically, boar meat was the feast of choice for honored guests. Boars are notoriously fearless. They challenge all who challenge them, man and beast alike. Because they were so difficult to hunt, serving it to guests was a way to show respect and generosity to your visitors. Plus, it is mighty tasty.

Then there was that branch. Being at a winery, you would be forgiven for thinking that this bough is merely just a grape vine at first glance. Looking closely though, you can see that this is not any old vine, or a vine at all, but that it is an oak branch. Based upon the leaf on the branch, I believe a white oak branch, which is an incredibly significant image in itself. The oak tree is a symbol of strength, independence, and courage throughout many civilizations. In North American culture, they represent peace and calmness. To the Celts, the white oak epitomized both hospitality and bravery. It serves as a constant reminder that humans have the ability to overcome any obstacle in their path, while having the capacity to be kind to others – whether be they friend or foe, stranger or neighbor.

These symbols, the Boar and the Oak, intertwined at the gates of Eastwood, subconsciously prepare you for your visit. Diana was extremely welcoming, giving up her free time to meet me during off hours not once, but twice, so that we could complete the interview. The feel of the newly constructed Barn tasting room, with its gorgeous copper bar and wooden beams, was warm and inviting. The stage at the rear of the building normally reserved for musical talent had a plethora of crafts laid out for any kids that join their parents on a visit.

She also told me about the challenging terrain that Athena had to overcome in order to get Eastwood up and running. They had an enormous amount of landscaping to do in order to create the terraces that lead up to the Outdoor Tasting Room. It is a large property, almost 80 acres in size, but it is at the base of Carter’s Mountain. The effort that was expended in order to transform this property is amazing. Work that continues even to this day. And, they are still hard at it. Crews are working to finish up the Veranda, a covered patio section next to the barn for guests. They are still working on the stairway leading up to the Mountaintop. Throughout my visit, I saw little pockets of activity through the woods and up the hill. What they were working on, I’m not sure, but they were hard at it. After all, there are challenges to overcome, and guests to welcome.

We’ll return to the Boar and the Oak a little bit later, but I do want to talk a little bit about Eastwood’s fearless leader, Athena, first.


Athena Eastwood is the founder of Eastwood Farm and Winery, and, to hear Diana talk about her, she very well may be the favorite daughter of Zeus reincarnated. In my previous interviews with winery owners, I was surprised to learn that neither one was a planned endeavor. I asked my host if Eastwood Farm was an intentional undertaking or a happy accident like the others. She told me emphatically that it was most certainly planned. There was a reverence in her tone as she described it to me. Diana was looking slightly away as she spoke, almost as if her employer was standing just over my shoulder. I even had to look back once or twice to see if she was actually there. Athena decided to create a winery and made it happen. She made it happen in spite of all of the challenges that come with starting any business from scratch. She made it happen even though she had never been in the wine or winery business before. She made it happen regardless of the fact that there are almost 40 other wineries in the area, with more coming every year. She made it happen even with the terrain of Carter’s Mountain itself railing against her. Athena made it happen. You could feel that this was a strong woman whom Diana was speaking of – a woman that she held in high regard. A literal Goddess brought to life.

With as much respect and admiration Diana showed for her leader, she showed an equal amount of adoration and tenderness for The Sprite of Eastwood Farm. This would be Josephine, the golden-haired granddaughter of Athena Eastwood, who has an infectious ebullience about her that can be felt whenever she is on the property. When Diana spoke about Josephine running around the Barn, or climbing to the Mountaintop, or creating crafts while others are working, you could see the smile light up her face even behind that mask she was wearing. It was obvious that this little girl provided the childlike energy needed to perfectly balance the strength of the leader of Eastwood Farm. Unfortunately, I did not get to meet this little pixie for myself, but I thought that if I closed my eyes I would see her weaving in and out of the tables that surrounded us, her blond hair trailing behind like a dancer’s ribbon.

Strong women are the rule rather than the exception at Eastwood Farm and Winery. Just take a look at their website and you will see that the Eastwood Team is almost entirely female. It all starts with their leader, Athena. Having just finished Women’s History Month, it seems appropriate to be highlighting this woman owned, women led, four generation family business here at Ramble. However, that is more good luck than any sort of superior planning on my part.


As I stated earlier, there were challenges to overcome from the very beginning in order for Eastwood to become a reality. One of the hardest hills to climb was a mountain. Specifically, Carter’s Mountain. Eastwood sits at the base of Carter’s Mountain and the incline is steep. In order to be able to grow anything at the site, terraces were installed to prevent erosion and allow water to be distributed to the plants. This was a massive undertaking, but the end result offers spectacular views from the Mountaintop where the Outdoor Tasting Room is located. I was able to see all the way to Afton Mountain from there, which is rare being so close to Downtown Charlottesville. There are almost two miles of hiking trails to enjoy, both short loops and long, and they offer outdoor yoga classes at the Mountaintop.

Sadly, the soil does not allow for vines to be grown, they are on the wrong side of Carter’s Mountain for that. But, as with all challenges, other opportunities can be found. While the soil isn’t appropriate for grapes, it is great for the apples that the mountain is famous for, as well as their green oddly shaped cousins, the pear. They are planted on the Terraces that lead up to the Mountaintop and were blooming while on my visit. It was calming and artistic, a lifelike Bob Ross painting, as I stood amongst them, my eyes closed, a gentle breeze bringing the scent of spring to my nose, and the sun warming my face. I could have stood there for hours that day and been perfectly happy not to encounter another soul.

Alas, I did have to return to work. But, not before sampling some of their wines.

I returned to the Barn and Diana asked if I would like to have a tasting. I normally do not do wine tastings on my visits, or much at all really, but I made a sort of New Year’s resolution to try more wine this year, so I happily accepted her offer. I did ask that she go extremely light on the pour. It was early in the day and I needed to return to my office. I noticed as she prepared the flight that it did not appear as though she heard my request. I was going to have to muster all of my limited will power to not drink all that was poured in each Eastwood glass, as I abhor wasting good alcohol. I am happy to report that I was successful in my endeavor and made it out of there safely.

She brought the wine over to one of the couches and provided me with a list of the varieties, along with instructions for the proper order to taste. Before sampling, as I was taking a few notes on the wines, I asked Diana how she got to be the Outdoor Tasting Room Manager. Had she worked at other wineries? Was she in the hospitality business before? She told me she worked in retail before coming to Eastwood and that she was an Art History major. I kept the conversation going, asking if those experiences helped with what she is doing now. She made an off-hand comment that kind of stuck with me that I wanted to share. She said that her Art background helped tremendously because it really applied to wine. A hundred people can look at the same painting and each one see something different. You can’t tell someone what they should see or feel when looking at Art. The same applies to wine. You can’t tell someone what they should see or feel when looking at Art. The same applies to wine. You can’t tell someone that this is a good wine and that is a bad wine. It’s extremely subjective and varies between each person. You just have to get out there, taste different wines, and you will like what you like.

I tried to keep this little bit of advice in mind as I started my tasting. In the past, I have always been much fonder of red wines than white wines. I enjoy cooking and use the reds frequently. I tend to like things with a bit of spice, and those are usually more my speed. I expected to like the red wine offerings. And I did. The Meritage and Tall Tails Merlot were both excellent, but I was – not shocked – okay, maybe a little shocked – that my absolute favorite was the Tall Tails White Blend. It is made from apples and pears that they grow onsite, and I thought it was fantastic. The 2019 Vintage just won a Silver Medal at the Governor’s cup and I can see why. Diana also let me know that they will be making it into a cider soon, but I would recommend getting out there to get a sample of the wine version before they do so. I’ll be trying the cider when it comes out, but I also bought a bottle of the wine to have at home. Maybe I’ll share with the Missus. Maybe I won’t.

That is not the only one of their wines to receive accolades at the latest Governor’s Cup. Their Meritage, Chardonnay, and Merlot all took home hardware, as well as their Raspberry Rosé. The Rosé, like the White Blend, took home a Silver Medal and is made from fruit grown on the property. Diana informed me that Josephine is especially helpful on those few days that the whole staff trek off to pick raspberries from along the hiking trails to make this vintage. Plans are in the works for blueberries as well. Close to Downtown yet surrounded by nature. Eastwood has the best of both worlds.

I thoroughly enjoyed my visit to Eastwood Farm and Winery. It is a beautiful site to spend the day drinking wine, relaxing on the Terraces, hiking through nature, or having a dream wedding on the Moutaintop. It is so calm and serene; you would never know of all of the hard work that went in to making Eastwood a reality without a little hunting to learn the story.

All of this leads back to the Boar and the Oak. Starting a business, any business, is not easy. Starting a winery, on the side of a mountain, without the right soil to grow grapes, with dozens of competitors in the area, during a pandemic is hard. But, the Eastwood Team, like the Boar, like the Oak, and like their Leader, have persevered. They have fought against obstacles that would cower lesser mortals and have triumphed. They have gained strength through their battles. They have done all of this with a welcoming smile on their face and an open heart for all of us strangers. The Boar and The Oak, Strength and Hospitality, The Goddess and The Sprite – They all meet at Eastwood Farm and Winery in perfect harmony.

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