6 Best Wineries near Keswick

“Our wedding day at Keswick Vineyards was perfect from start to finish - not an exaggeration. Everyone on staff made the entire day seamless, so we were able to truly just arrive and enjoy the day. When weather caused a hiccup in our day, our cocktail hour was moved under the tent no problem, drinks were brought to the wedding party while we waited out the storm, and we were able to keep to our schedule due to Cindy and team's fantastic planning. The venue itself was beautiful - the pool, house, and vineyard made the perfect photo backdrop, the carriage house where we got ready was the perfect secluded spot for our wedding parties, and I just truly didn't have to think of a single thing. The inclusions to the venue rental (tent, chairs, tables, etc.) made planning that much easier, along with vendor recommendations, and Cindy and team are true professionals who know what they're doing and will ensure your day is just about you and your love story. We were also lucky to have Cindy as our month of coordinator, which if you're lucky enough to snag one of her limited spots, DO IT! Going into our wedding, I truly felt so stress-free and like everything was out of my hands and handled. I truly cannot recommend getting married here enough, and it makes me so happy that we'll be able to share a bottle of Keswick wine together each anniversary. Just truly can't fit how wonderful this whole team and venue is in a single review. I am so grateful our wedding day was so special and perfect thanks to this place. This is a dream venue.“

“My husband and I enjoyed our visit yesterday and were very pleased with all of the wines that we tasted. The fresh baguette and goat cheese were yummy. We had a very knowledgeable server that answered all of our wine nerd wannabe questions 😂 We especially enjoyed chatting with Gabriele he is a very sweet man and the history and stories he shared were an extra special treat.“

“We had a wonderful time at Chestnut Oak Winery. Started with a red and white flight, both quite enjoyable. Sarah provided a bit of knowledge in the red blend (Bordeaux style) and also let us know that Cab Franc was being planted! A 4-5 year wait for it to reach our lips, but it's starting. Followed by a glass of Euclid and Petit Verdot. Wonderful time.“

“Eastwood is my favorite winery in Charlottesville and has been for years. When my 50th birthday was on the horizon, and I decided to have a party, Eastwood was the first place that entered my mind. Given the time of year and the day of my birthday, Eastwood was already busy with many events and could not accommodate my request. But I learned that Eastwood had recently bought the former Michael Shapps building on Avon Street. It is now the Virginia Wine Collective (VWC), and the floor above the tasting room is a lovely event space with the ability to serve delicious Eastwood wine and offer amazing food. Once I visited the space, I knew that I had found the perfect place to have my party. I began working with Mary on the menu and food timeline and throughout the process she was available to answer my questions and offer suggestions.

The space comfortably held around 35 guests, snack table, bar, food buffet and dance floor. Mary and Gaby handled the bar, while Corey worked his magic in the kitchen. The food options were fantastic. The feedback was great. And for me, I was thrilled that Mary and Corey made sure there were vegan options – more than I had expected. The pasta dish, roasted veggies and warm chickpeas were all vegan. (And my carnivore friends/family did not notice.) The warm chickpeas were a huge hit – I’ve been asked to get the recipe.

A huge THANK YOU to Mary, Gaby and Corey for helping me make my party at VWC a memorable one for me and my guests.“

“Let me start by saying I don’t normally write reviews, but I HAD to post something about this place.
We stumbled upon this absolute treasure after having a not so great tasting at another vineyard. We had about an hr and a half to kill before our next tasting appointment and Chisholm was perfectly on the way to our next vineyard.

BOY am I glad we stopped for this impromptu tasting. The grounds are beautiful and the tasting room/ patio area looks like something out of the secret garden. The second we walked in the door- we were greeted by Mary and Andrea (owner) who were both sweet, engaging and hospitable. Their knowledge of wine, the family history of the farm and the tasting itself was next level.

Do yourself a favor- get the frose, ask about Gigi (total badass), nibble on some chocolates and make sure you add this hidden gem to your vineyard itinerary- we certainly will be back.

Thank you ladies for turning an impromptu tasting into our favorite one of the day!“

“Jefferson Vineyards is an absolute gem in Virginia wine country. The setting is stunning, with rolling hills and a peaceful atmosphere that makes for a perfect escape. The tasting experience is exceptional—each wine is thoughtfully crafted, and the staff is knowledgeable, friendly, and passionate about what they do. I especially appreciated how they shared the history behind the vineyard and guided us through the unique flavor profiles of their wines.
What truly set this visit apart was the incredible customer service. I called ahead and spoke with Lisa, who went above and beyond to help me set up my son’s impromptu proposal. Her kindness and attention to detail made the moment unforgettable, and I’m so grateful for her help in making it special.
The quality of the wines truly stands out. From crisp whites to bold reds, every pour reflects care and expertise. The grounds are well-maintained, offering beautiful views that pair perfectly with a glass of wine. Whether you’re a seasoned wine enthusiast or just looking for a relaxing day trip, Jefferson Vineyards delivers an unforgettable experience.
Highly recommend visiting for a tasting or enjoying a bottle on their scenic patio—you won’t be disappointed!“