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    Chrysalis Vineyards

    3.3 (433 reviews)
    Closed • 12:00 pm - 8:00 PM

    About Chrysalis Vineyards

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    Elvin M.

    Another beautiful winery here in Northern Virginia. Service food and wine were all amazing. Definitely a revisit and another winery tht a must if your visiting the beautiful Virginia wineries.

    Upper deck, adults only seating area
    Vanessa B.

    This is a beautiful and spacious winery, don't get me wrong. The service is friendly, the wine tastes good. They can assemble a charcuterie board for you, but you've got to buy the meats and cheeses piecemeal. The pico de gallo left a lot to be desired for the price. There is an upper floor where it's 21+, and the outside deck overlooks the grounds and the mountains. However it is insanely hard to enjoy when there are small children running around, because their noise carries onto the deck, no matter where they are. Cannot wrap my head around parents not only bringing their kids to a winery, but both parents drinking as well. I don't think I'd return to this winery because they allow kids, whose parents treat the place like a sort of a daycare or jungle gym.

    Outside
    Angela B.

    I stumbled upon Chrysalis driving to a different vineyard/winery. I found the entire location super cute--I can only imagine the views when the leaves are on the trees and/or changing colors. There's plenty of seating for a bunch of small groups and even space for family groups. Make sure you venture everywhere. I failed to go upstairs... I was greeted by a nice lady and helped by two gentlemen (one took my order and the other one poured my flight). Not being familiar with this location or its wines, I decided on the "can't decide" flight. Should I find myself out that way again, I'll definitely give it another try. Their menu looked delicious with their cheese, flatbread/pizza, and sandwich options.

    Wasabi deviled eggs
    Rachel K.

    My boyfriend and I stopped by for Friday evening dinner and drinks. We ordered 1 white wine flight, the margarita pizza, wasabi deviled eggs, and 1 bottle of the 2023 Albarino Verde. We really enjoyed the Albarino Verde. This wine was crisp, refreshing, and perfect for a summer day. The pineapple and grapefruit were the most noticeable notes. The deviled eggs were good but not quite worth $12. I didn't taste any wasabi which was disappointing. The margarita pizza was great! I would definitely get this again. Simple but delicious. The dough itself was really good and we enjoyed the thinness of the crust. It also came out piping hot. The winery itself is very pretty with a lot of outdoor seating. It ended up raining when we were there which was no issue since there's also some seating indoors.

    The "Can't Decide" flight.
    Erik B.

    The views of the surrounding countryside are good from the outdoor patio area. The wines are okay. Did the "can't decide" and the "Norton" flights. The staff were not welcoming but not rude either, just there. I asked for recommendations and they pointed out popular wines. It was good to try another winery.

    Outside
    Sarah H.

    Great views of the rolling hills and friendly service. Kids welcomed (but upstairs is adults only). A large menu, pizza, charcuterie, sandwiches, etc. but the food was just ok. I got a flight and did not like any of the wines; many were very very sweet.

    Nina R.

    Nice service and scenery. Beautiful view since the winery sits way up at the top of the hill. We went on a Saturday afternoon for lunch. I had a chicken pesto sandwich with chips on the side which was delish. Others ordered the pizza, cheese, and hummus platter. Note: no outside food allowed. Sorta bummed because I packed a small travel cooler with fruit and snacks, but I didn't check their website in advance. Highly recommend.

    Cheese pizza
    Lia M.

    We had an amazing time at Chrysalis. The staff was so friendly and welcoming, which really helped. It wasn't super busy during our visit, which was nice. I love that they have a childfree area. We really, really enjoyed the wine. I did the dry flight and my friend went with the Norton flight. I was really impressed by the wine. The few VA wineries I've been to in the past few years have left me unimpressed. But Chrysalis has great wine. My favorite was the alvarinho verde. I got a glass after and then my friend got a glass of her favorite, the Sarah's Patio. They also have great food so you don't need to worry about bringing anything (which isn't allowed anyway). The pizza crust could've used more color, but overall the flavor was on point. I'm looking forward to returning in the spring as they have a gorgeous outdoor area.

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    Thank you for visiting us Nina! Come back and see us soon!

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    Jennifer M.

    Thank you for visiting us Greg! Come back and see us again soon.

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    Page 1 of 11

    Ask the Community - Chrysalis Vineyards

    Review Highlights - Chrysalis Vineyards

    “Sarah's Patio Red and White are also a great wine to come home to after a long day at work.”

    Mentioned in 23 reviews

    Read more highlights

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    50 West Vineyards

    4.1(154 reviews)
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    My friends and I visit Middleburg yearly and choose a different vineyard each visit. We absolutely…read moreloved 50 West from the moment we walked in the door. It's absolutely beautiful inside and outside. You won't want to leave. Gunner was our Sommelier and probably the best in Middleburg. We each did a wine tasting and the way he described the wines and educated us was amazing. I was so intrigued. The wines are wonderful!! After we had the wine tasting at the bar, we bought a bottle of our favorite wine from the tasting, a box of chocolates and candied pecans, and sat on the upstairs patio. The view is stunning. It had just rained and it was absolutely beautiful outside. It's a must when you're in the area!!

    Gorgeous winery with spacious grounds and comfortable seating. The service here is friendly, and…read morethey'll accompany you out to your table with your wine or food. This is an ADULTS ONLY winery which is just so fantastic. They do play music over the speakers, which was a twinge loud, but it wasn't too bothersome. There's charcuterie as well as more substantive foodstuff to choose from, as well as chocolates -- omg they have chocolates (a little box of 7 or 8 truffles). The wine here is good as well. The only negative is you can't do a self guided flight, you've gotta have the sommelier do a guided flight. But yeah, my favorite winery so far.

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    50 West Vineyards - A very good bottle of wine.

    A very good bottle of wine.

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    Gorgeous interior on second floor

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    Greenhill Vineyards - Love this view!

    Greenhill Vineyards

    3.8(289 reviews)
    2.5 mi
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    Free parking

    My husband and I spent a delightful afternoon with friends at Greenhill Vineyards in Middleburg,…read moreand from the moment we arrived, everything was a perfect 5-star experience. First, a shoutout to our wine server, Hannah, who was absolutely fantastic. She was friendly, knowledgeable, and passionate about the wines without ever making us feel like we needed a sommelier certification to enjoy them. She guided us through the $20 tasting, which included a wonderful mix of whites and reds. It worked out perfectly because I'm a white wine fan while my husband prefers reds, so naturally we shared every pour and declared ourselves a two-person tasting committee. Now let's talk about the food. The truffle popcorn should probably come with a warning label because it is highly addictive. We kept saying "just one more handful" until the bowl mysteriously emptied itself. The fresh baguette with pimento dip was equally delicious and paired beautifully with the wines. The winery offers plenty of seating options, whether you prefer lounging on the grass, relaxing indoors, or enjoying the covered patio. We chose the covered patio, which provided the perfect balance of fresh air, vineyard views, and shade. And yes, I'm actually going to mention the bathrooms. They were some of the nicest winery restrooms I've encountered--modern, spotless, stylish, and clearly well-maintained. It's one of those little details that says a lot about the overall experience. Great wine, delicious food, beautiful setting, immaculate facilities, and outstanding service from Hannah. Greenhill Vineyards has earned every one of these five stars. We'll definitely be back for another "research trip" in the near future.

    Greenhill Vineyard is hands down my favorite vineyard in Middleburg--and the perfect way to start a…read moreday of wine tasting. We came here first before heading to brunch and a second winery, and honestly, it set the tone for the entire day. The grounds are absolutely beautiful--peaceful, scenic, and everything you want when you're trying to escape the city for a bit. The wine selection is solid, and everything we tried was smooth, well-balanced, and easy to enjoy with friends. It's the kind of place where you can actually relax, take your time, and be present. What I love most about Greenhill is the vibe--it feels elevated without being pretentious. Just good wine, great views, and the kind of atmosphere that makes you want to stay a little longer. If you're planning a Middleburg wine day, start here. You won't regret it.

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    Greenhill Vineyards - Great wine for a great day! Go seyval blanc!

    Great wine for a great day! Go seyval blanc!

    Greenhill Vineyards - © Greenhill Winery and Vineyards

    © Greenhill Winery and Vineyards

    Greenhill Vineyards - Entrance to Greenhill Winery

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    Entrance to Greenhill Winery

    Quattro Goomba's Winery - Cabernet slushy

    Quattro Goomba's Winery

    3.8(459 reviews)
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    We have been coming to Quattro Goomba's for several years but I felt the need to leave a review…read morebased on our recent experiences. We hosted a bridal shower here in February, and it could not have been easier to work with them. Despite record cold temperatures that day, everything was perfect. The wine, pizza & charcuterie could not have been better, and all of the guests loved the mimosa bar they did for us. The space we used was lovely. The little house on their property was the perfect setting, and the attention we got before and during the event was perfect. Jody was a dream to work with on the planning, and she made sure it went off without a single issue. I couldn't recommend it more. We always enjoy coming out to hear local musicians, (especially our favorite local artist Gary Smallwood), and great beer/wines + their legendary pizza = a great way to spend a day or evening. Also, the staff couldn't be nicer. It must be a great place to work because they're always happy, kind, and helpful. We tried the tater tots last night, and oh my goodness they were probably the best we've ever had. So with all the brewery and winery choices in NoVA, this one tops our list and remains our favorite. For your next outing (or party/shower/event) this IS the place. Trust me. 10/10

    The winery has ample space for seating indoors and outside, great for groups. There are numerous…read moretvs, drink options from beer (IPOs) cocktails and wine slushies. They have a fairly extensive menu for the standard winery/vineyard offering subs, sides, pizza and sandwiches. The pizza has a thick crust, typically not my preference, but honey this is crisp and buttery. The pizza toppings are typically crumbles of the protein which are also nicely crisped. It hits the spot if you're drinking a good bit.

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    Quattro Goomba's Winery - Goodness.

    Goodness.

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    Pizza menu

    DiVine Wine Tours - Wine tour

    DiVine Wine Tours

    4.9(49 reviews)
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    For my 40th Birthday, I booked DivVine Wine Tours and it was an amazing experience. First, the…read morebooking was easy and Amy was super responsive. We had some last minute additions and she was very accommodating and efficient. Once we were picked up by our driver, Natalie, we were on our way. She was timely and communicated with me ahead of time. Additionally, she was accommodating to my demanding group who needed temperatures adjusted (this was early August) and music selections (she asked if anyone had a playlist). All of the vineyards were immaculate. The last vineyard had not updated their records to reflect our late additions, but that was not on DiVine. Pictures were taken, Natalie engaged without being creepy and communicated throughout the tour. I honestly cannot wait to do this again.

    We had a fabulous time on our Wine Tour with DiVine Wine Tours this weekend ! I found DiVine Wine…read moreTours online when planning my sister's Bachelorette weekend getaway in Leesburg. Booking the tour was easy, I did it all on their webpage. Communication prior to event with DiVine staff member Amy was clear and concise. I was confident in the plan , the lunch orders, the schedule etc. I love how the tour made the day easy and relaxing for us! Melissa picked us up promptly at our AirBnb Cottage. Our first stop was Zephaniah Winery. It is a sweet and gorgeous family operated business. The family is super friendly and amazing! We adored talking to Bonnie! She shared about the history and also we admired her colorful flowers she has planted all around. The wines at Zephaniah were exquisite! Our second stop was Williams Gap Vineyards. It was definitely a beautiful ambiance with friendly staff. We loved how cozy, innovative, and spacious the place is! Melissa was an amazing tour guide! She always checked in on us, made sure all was going great, she took great pictures of the special day! I highly recommend DiVine tours!

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    DiVine Wine Tours - First Stop- Zephaniah Winery

    First Stop- Zephaniah Winery

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    Boxwood Estate Winery - Courtyard

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    We had such a great experience! Caroline and George were so nice...their customer service was just…read moreexceptional!

    I finally made my first visit to Boxwood Estate Winery, and I can completely understand why…read morereservations can be hard to come by on busy weekends. We visited at an unusual time on a weekday, which ended up being perfect because we essentially had the entire space, including the cave, to ourselves. The property is beautiful from the moment you arrive, surrounded by the vineyard, and the winery itself has a very modern, sleek, clean aesthetic. We booked the Estate Pairing, which combines their wines with different food pairings. Mark was our server and was fantastic! He explained each wine and pairing, answered our questions, and made the entire experience feel welcoming and relaxed. They were also able to accommodate dietary restrictions for my friends, which was a huge plus. Erin the general manager is great as well! Overall great service. Something I especially appreciated was the pacing. At some wine and food pairings, someone stands there while you taste everything, which can feel a little awkward when you're trying to eat. Here, they explained everything and then left us alone to actually enjoy the food, wine, and conversation at our own pace. They checked in afterward to hear what we thought and offered us the opportunity to try something else, order another glass, or purchase a bottle to take home. We also tried their Crémant, which was particularly fun because this is the first year Boxwood has produced it. Overall, this was such a relaxing and enjoyable wine experience. Beautiful property, wonderful service, thoughtfully done pairings, and plenty of time to actually enjoy yourself. I would definitely return and would recommend making a reservation in advance, especially if you're planning to visit on a weekend.

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    Chrysalis Vineyards - winetastingroom - Updated October 2026

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