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    The Greencroft Club

    4.3 (8 reviews)
    Closed • 11:30 am - 8:00 pm

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    Went to Wednesdays Around the World night and absolutely loved it! Great food and friendly staff
    Gabe A.

    Had a really great experience here at their Wednesdays Around the World night. Food was outstanding and loved how tranquil it was.

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    Glass House Winery

    Glass House Winery

    (129 reviews)

    $$

    My mom and I spent four nights at Glass House Winery & Brewery for a mother-daughter trip around…read moreCharlottesville, and it ended up being one of the highlights of our entire trip. Glass House is in Free Union, about 20 minutes outside downtown Charlottesville. The location was perfect because it felt peaceful and tucked away in the country, while still being close enough to explore Charlottesville, Crozet, wineries, orchards and hiking. The hospitality was what really made the stay special. Kristin, the chef at the B&B, is incredibly warm and welcoming, and breakfast at 9 AM each morning was something we genuinely looked forward to. She personalized meals around our likes and dislikes and used fresh, local ingredients. During our stay we had blueberry ricotta pancakes, peach and Brie cinnamon bread pudding, latkes with breakfast meats, and an egg quiche with sausage and vegetables. There was also yogurt, fresh fruit, smoothies and coffee available throughout the day. The B&B has a very personal feel, with cookbooks throughout the house, unique Nicaraguan tropical decor and themed rooms such as the Chocolate Room, Wine Room and Under the Stars Suite. The bedding was comfortable, with both communal spaces and areas where you could have some privacy. The attention to detail was wonderful. We had a chocolate surprise, and a complimentary glass at the winery for being guests. I'm not much of a sweets person, but the chocolates were somehow exactly what I wanted all weekend, especially with a glass of wine. You can also purchase bottles and chocolates after hours, and they recently launched a wine club. I also really liked that the owner is actually around the property and winery. He was happy to answer questions, talk about the area and share the history of the vineyard, which made the experience feel much more personal. The winery is about a five-minute walk from the B&B and is open Wednesday through Sunday. The glass house itself is beautiful, almost like a greenhouse, with water elements, accent lighting through the greenhouse plants and vineyards located directly behind it. There are places to sit and watch the sunset with a glass of wine or enjoy coffee in the morning. The sunsets were incredible. On a clear night, the colors over the vineyards seemed to change every few minutes, and it was incredibly peaceful. We also saw wildlife around the property. The winery offers chocolate and wine pairings, reasonably priced wine, live music and food trucks. The live music was especially good and covered different genres throughout the weekend. We even had a seafood boil from one of the food trucks. The staff was friendly and knowledgeable. The brewery is another three-minute walk from the B&B and is currently open Saturdays. Having both a winery and brewery on the same property is something I didn't see anywhere else during our trip. We tried the pineapple sour and coconut stout, and they have a light beer coming soon. The brewery itself is also really unique because it was made using leftover wine bottles. There is plenty to do without leaving the property, including a saltwater pool, jacuzzi, live music, food trucks and plenty of places to relax. We also used Glass House as our home base for exploring the area. Carter Mountain Orchard was fun for apple cider donuts, cider and other treats. We visited Pippin Hill, Hark Vineyards, Eastwood Estate and Knights Gambit, each with a completely different atmosphere. We also hiked Humpback Rocks and Crabtree Falls. Humpback is definitely strenuous, while Crabtree was more manageable and had beautiful views. We spent some time in Crozet and downtown Charlottesville as well. We had a delicious meal at Smokehouse BBQ at Piedmont, and downtown Charlottesville's Downtown Mall was fun to explore. Vita Pizza was delicious and very accommodating with our food variations. One thing future guests should know is that most restaurants outside of Glass House are about 20-30 minutes away, so keep some snacks on hand and make dinner plans earlier. Most wineries also close around 5-6 PM, which actually worked well for us because we could enjoy the wineries during the day and get back to Glass House in time for the sunset. Our four-night mother-daughter trip was exactly what we wanted, and Glass House was the perfect home base. What made it even more memorable was the people we met and how genuinely welcomed we felt. There are plenty of beautiful wineries in the Charlottesville area, but Glass House felt different. You get wine, beer, live music, food, hiking, a pool, a jacuzzi, beautiful sunsets and a truly personal B&B experience all in one place. I genuinely think it would be a missed opportunity to visit the Charlottesville area and not experience Glass House. We will absolutely stay here again and recommend it to anyone visiting. You get the peaceful small-town feel along with beautiful, friendly amenities, and we truly can't say enough good things about our experience.

    Probably the most unique vineyard we've ever visited. Unique indoor greenhouse--beware of…read moremosquitos! Disappointed to be eaten alive while seated inside. We did not love the wines but the Pineapple gose was delicious!

    Eastwood Farm and Winery - Inside

    Eastwood Farm and Winery

    (104 reviews)

    $$

    We really enjoyed our wine, blueberry cider, and food at Eastwood! Plus, the staff are friendly…read moreand want to ensure you have a great experience. We enjoyed the Gold Medal Tasting. This assortment had two whites and two reds--all of which earned gold medals at competitions. For lunch, we shared the grilled cheese with apple slices and the Eastwood salad, which included apples, blue cheese, nuts, and mixed greens. All were delightful. The tasting room has a warm vibe of a country gathering place with tables, a bar, and a stage. They also have outside seating. Their fermentation room has a glass wall that looks into the tasting room so you can see the tanks. Eastwood is located not far from Monticello and other wineries in the area. I recommend it as a definite stop on any wine outing.

    A friend and I stopped here on a recent trip to Charlottesville. I was surprised by the number of…read morefamilies with children, as this is not something I'm accustomed to from living in Washington state for many years. We walked inside and found a great space that included a bar, ample seating, and a stage, where a singer was getting ready to perform. I decided on the White Reserve Tasting, and was able to swap out the oaky chardonnay for the Woodland White blend. My friend and I got a table outside as the weather was nice. We enjoyed our wine and people (and dog) watching. My favorites were the 2024 Viognier and the Woodland White. The 2024 Petit Manseng was good, but a bit tart, and the Artist White blend was too dry for my liking. This is a great winery that you should visit when in the area, that's both kid and dog friendly.

    The Greencroft Club - venues - Updated September 2026

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