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Upper Shirley Vineyards

4.1 (196 reviews)
ModerateWineries
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Updated 1 month ago

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Scott G.

Great local winery not to far from us at a historic plantation house on the James. Great views tasty food and wine!

Chris K.

Upper Shirley Vineyards is a great place to get away and enjoy good food and wine while taking in views of the James River. Both the interior dining area and the long porch in back contain ample comfortable seating. We dined there for lunch and enjoyed a flight of their white and rose wines, as well as a glass of their Divertido, which is a red wine. The wines all complimented the food. I especially liked the sparkling rose! It exudes flavors of strawberry. For lunch, we ordered the grilled cheese sandwich composed of bacon, tomatoes, and spinach with sharp cheddar and havarti cheeses. We also ordered the turkey, bacon, cheese, arugula panini. Both sandwiches were excellent and came with multiple choices of sides, and we chose the yummy house chips. The restaurant was busy and had more than enough staff to accommodate everyone. They were informed and cheerful. After lunch, we strolled the back of the property, which overlooks the James River. It begins with a patio containing couches and chairs under the cover of large umbrellas. It's a relaxing space to sip wine and enjoy time with friends. Beyond the patio is a large grassy area leading to an area overlooking the river. Upper Shirley Vineyards also has a banquet facility. Parking is good and easily accessible.

Kel R.

Food was amazing! The brussel sprouts and the truffle fries were soo good! The wine was great too! We got a bottle to celebrate for our wedding anniversary today!

White wine flight
Crystal T.

I really enjoyed the bright lighting in dining area. I ordered the white wine flight with the spinach and artichoke dip. I enjoyed the #2 white wine the most out of the flight. It was the very fruit forward and light which is what I enjoy. The spinach and artichoke dip was nice but a little oily. The crostini was toasted perfectly. I had a great experience and will be back!

Maria T.

Update on Upper Shirley! All the Stars!! Our work had a gathering here... a private wine tasting by the incomparable Nate! He was so knowledgeable yet not at all condescending. He was amazing, his service was on point! The grounds are gorgeous. The estate is fabulous and we all had a grape time!! We had apps with our tasting and afterwards we enjoyed an exceptional lunch on the veranda overlooking the knoll and the river! I had the charcuterie board (to match my earrings!) and the rest of our clan had burgers, pulled pork, salads, and dandy sandwiches. As we dined and sipped our way to elation... we received incredible attention from the servers. No whining from us... we had a blast! To top off the afternoon, we enjoyed nightingale ice cream sandwiches which hit the sweet tooth to perfection! Upper Shirley is Tops with us!!

The view from the back deck!
Sandra S.

The ambiance and views are insuperable, the food is not bad but nothing special either, it is a place to come for the experience. The service was good. We will be back!

Crab Dip, Truffle fries, Oysters Rockefeller
Nicole N.

Decided to take a road trip for some wine and ended up here! The place is stunning, and has plenty of outdoor space for an event like a wedding. The inside has a restaurant feel without feeling too formal. We decided to sit in the back with a view of the water. There's tables on the deck with additional lawn seating (the lawn is huge). My brother and I both got a flight and some shared appetizers. The food was an unexpected standout! I absolutely loved the collard greens in the oysters Rockefeller. We couldn't stop raving about the food after we left. We came here on a weekday afternoon so it wasn't too busy. They have a sign stating that there is a 2 hour seating limit for tables with a server but that didn't seem to be a problem for us. I'd definitely come back again!

Charcuterie board and fried green tomato caprese
Sandra B.

What a beautiful place to visit. Even though it's out of the way, the views are tranquil and perfect for a girls day out. The initial service to get seated is a bit confusing since the front attendant was missing, but once we were seated, the server was excellently attentive. The food and wine were deliciously paired. I got the white wine flight and had it with a charcuterie board and the fried green tomato caprese. It's a lovely place and somewhere I'd recommend those visiting nearby Richmond.

Parking lot
Nicole N.

First time here and had a great time!! Solid food and solid drinks! Their sparkling rose was pretty good! It was filled with fruity flavors but not too sweet. The mushroom flatbread was cheesy with mushroom slices, truffle oil, and arugula. I personally wish it could have been seasoned a little more but it was still yummy overall. The charcuterie board had your standard 3 meets and 3 different types of cheeses as well as some pickles and pickled asparagus. It came with a fluffy baguette! There was plenty of parking and seating options inside, patio, and outside. I liked the open space with live music, as well as the fairy lights on the patio. Tables were clean. The food came out pretty quickly and staff were nice. Would recommend!!

Truffle fries are delicious
Sara E.

This is probably my favorite winery around because it checks all the boxes-- has great food, a wonderful view and great wine! I love their wine flights, and that there's a variety of options. The truffle fries are delicious !!!! The water view is super nice, too.

Nicky S.

We ventured here by bike via the Virginia Capital Trail. They had plenty of space to lock up bikes and an ample parking lot for vehicles. As you arrive, you will enter alongside some horses meandering in a field. This kinda sets the scene for this lovely vineyard. We headed straight to the back field along the river and found a shady spot under a tree. You really couldn't ask for a better location. Some musicians were playing and we relished in the enjoyment of being in such a scenic plantation setting. We had a picnic lunch (chicken salad and a club sandwich) from their menu and it was delicious! We also enjoyed a bottle of the sparkling rosé. I would definitely come back here again!

Vernita T.

Great time for my friends birthday. We went in a Saturday 12-3. Extremely pack inside and out. The offer a wine tasting kit for$15 or in person for $25 We set outside on the patio. Took awhile to get my food as I joined the party later and it was packed but that would be my only critique! My mushroom flatbread was delicious! Only suggestion is to toss the arugula in olive oil and seasoning. Great experience and prices will definitely be back! Hopefully for the fried green tomatoes topped with pimento cheese!

Wine flight

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1 year ago

We have been there numerous times. Good food, service is attentive, very relaxing place

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2 years ago

Food was amazing and wine was even better. Great service and we were seated right away .

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Ask the Community - Upper Shirley Vineyards

Are children allowed?

Yes, children are allowed. Please give our restaurant a call if you have any questions!

Is the tasting room and restaurant wheelchair accessible?

I believe it is...

Can you bring your own food to this winery?

No outside food or drinks are allowed.

Don’t See Your Question? Ask Away!

Review Highlights - Upper Shirley Vineyards

The venue is gorgeous with large porch, patio, and lawn areas overlooking a wide expanse of the James River.

Mentioned in 18 reviews

Read more highlights

River Dog Winery - Wine flight where you can choose your own.

River Dog Winery

4.9(7 reviews)
7.0 mi

Wife and I visited yesterday. I'm not a wine drinker but I know what I like. It was very handy to…read morehave descriptions of the wines written out so we could choose which ones to taste. I hate going to a winery and not enjoying half the wines because what they say they are, are nothing like how they taste. That is not the case here at all! Debbie also labeled our flight tray, so there was no confusion over which wine was which. As far as the atmosphere, it was early on a Saturday afternoon and there was only one other couple there when we arrived, but more folks came in while we were enjoying our wine. We sat outside and enjoyed a beautiful day, but there is indoor seating and it is very nice and clean. Debbie (owner) was very friendly and informative about the wines. We did not try the snacks as we had had a large breakfast, so I can't comment on those. We bought 4 bottles of wine, which I felt were reasonably priced $15-$25 with a discount for amount spent, which was unexpected but nice. We will definitely return.

Very friendly, family-run vineyard and winery. The family converted a home into their tasting room…read more The winery has only been open for 3 months, so they were pouring all of their wines for the tasting (10+ for $15). The grapes are a bit younger (oldest vines about five years) so the flavors are sharp and punchy. There drinkable now but also will age well. They have quite a variety on the tasting menu - from port style, whites and reds. We had a great tasting experience with one of the owners and felt comfortable sitting and drinking wine after our wine tasting. No snacks yet, but they are planning on getting.

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River Dog Winery - Cute decor.

Cute decor.

River Dog Winery
River Dog Winery - Optional outdoor seating.

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Optional outdoor seating.

Saudé Creek Vineyards

Saudé Creek Vineyards

4.5(140 reviews)
23.5 mi
$$

What a beautiful establishment. Not only is the building interior and exterior beautiful, but the…read moregrounds are beautiful as well. I have been to Saude Creek, two times now. I do with there were a better offering of snacks/food available inside. But, there has always been a food truck available with hot food offerings. As for activities I have been there once for an even Rusted Rabbit has hosted. While there I was able to sample/purchase some wine to try. The event was nice and very well thought out. We were located upstairs which has a balcony that over looks the back of the property. My friends have raved about their wines and even sangria. There has been people there singing and a band once. So it was nice to have some entertainment. I enjoyed sitting outside on the porch. We even sat down below the exterior where it was quieter. The staff have always been accommodating, knowledgeable on their product and kind. The grounds has always been well put together and clean. There is defintly attention to detail throughout the property.

Great rainy afternoon at Saudé Creek Vineyards with friends! This afternoon we met up with friends…read morefor a little wine therapy. All of their wines are great, and we were able to bring in our own food spread, which makes the wine even better! Added bonus, there was live music to brighten up the dreary day. On a sunny day, this winery has gorgeous grounds to enjoy the weather.

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Saudé Creek Vineyards
Saudé Creek Vineyards
Saudé Creek Vineyards

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New Kent Winery - Front of New Kent Winery

New Kent Winery

3.2(193 reviews)
16.2 mi
$$

A fun stop! Lots of seating areas which made it nice to spread out. Live music some weekends…read morewhich was really nice. The wines are good and the food selection is plentiful. The baked Brie was our favorite! It wasn't crowded so it wasn't bad going inside to order but when crowded it might be a pain. The staff were very friendly and welcoming!

Review for New Kent Winery - Where Vines Meet Vibes…read more We popped into New Kent Winery one sunny afternoon while cruising down to Virginia Beach -- because what's a road trip without a little wine country detour, am I right? This place? Massive. Immaculate. It's giving modern farmhouse chic meets Napa-lite. Think soaring ceilings, airy spaces, and a patio that overlooks the vineyards like it was built for sipping and Instagramming. If your aesthetic is "refined with a hint of rosé," you'll be right at home. They've got a monster wine list -- obviously -- but plot twist: they also brew their own beer(Talleysville Brewery). So, if you're rolling in with someone who's more hops than grapes, they're covered too. The food menu is small but mighty -- just enough to keep your buzz from turning into a dizzy spell. We ordered the spinach dip with tortilla chips (creamy, garlicky, devourable) and paired it with a flight of four beers: * Cerveza con Limón y Sal - A crisp Mexican lager with zesty citrus vibes. Summer in a glass. * Old Church Vienna Lager - Malty, slightly sweet, with a bit of a bitter bite. A polite handshake of a beer. * Double Cut IPA (Galaxy & El Dorado) - Hoppy, punchy, and packing that metallic aftertaste my wife adores (I'm still working on liking it). * Black Knight Stout - A dark and brooding Irish stout with Bugle Call coffee. Basically, an espresso martini's beer cousin who rides a motorcycle. Service? Smooth, friendly, and on top of it. No complaints there. Overall, New Kent is the kind of place that makes you say, "Wait, why don't we stop here more often?" Whether you're in it for the views, the vibes, or a good pour, it delivers.

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New Kent Winery - Sweet Virginia

Sweet Virginia

New Kent Winery - Main entrance

Main entrance

New Kent Winery - Wine tastings to the right, beer tastings to the left

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Wine tastings to the right, beer tastings to the left

Jolene Family Winery

Jolene Family Winery

4.5(57 reviews)
11.7 mi
$$

Came here for a girls wine tasting. Jolene Family Winery is located in Kent County, VA, about a 40…read moreminute drive from Richmond. The winery is situated by a river. There was parking available, but if you come late, you may have difficulty finding a spot. We entered the building and proceeded to the counter to check out what they offered. The staff were pleasant and patient in explaining the various wines and other beverages they offered. The ambiance was chill, as we had visited on a Saturday which also included a food truck onsite and live music. We settled on the nine-sample tasting which was only $20, a great deal in our opinion. It consisted of 3 whites, 1 rose, 4 reds, and one tasting at the end that we could choose the flavor: raspberry or peach; some chose raspberry some peach. There was plenty of seating inside and outside. There was an outdoor covering, in the event of inclement weather, which also housed a fire hearth, good for a fire roaring chilly night of wine tasting. There were also outside open seating with tables. We also noted that folks were bringing their own chairs, which was a good move given that the crowd grew the longer we were there. Our tasting was nice: we were given a metal tray that held our tastings with a paper under that identified each wine and also given a paper with a description of the notes of each wine. It was mix of dry and sweet red and white blends, which was good. We all had a favorite with one clear winner: the last peach wine of the tasting! You could also purchase wine by the glass, bottle, or to go, in addition to wine slushes. They also had snacks such as cheese, crackers, dried meats, perfect for making your own charcuterie board to nibble on with your wine. There were also folks who brought their own snacks. The food truck on site was Cousin's Main Lobster specializing in all things lobster. They had the traditional lobster roll, lobster grilled cheese, lobster quesadilla , lobster tacos, lobster bisque, etc. We ordered the traditional lobster roll with mayo (they also had one with garlic butter and one with Parmesan), lobster quesadilla, lobster tacos, and shrimp tacos. The food was ok, nothing stood out overall. The seafood was fresh and did lack seasoning, but overall, good. The winery also had local artisan items for sale such as jewelry, t-shirts, wine glasses, throw pillows, etc. We also saw that this was a family and dog-friendly winery as there were plenty of both there. The winery overlooked a lake, which was picture perfect. There was a duo playing music under an outside pavilion stage. All in all, a great afternoon sipping wine with friends and family.

Took a random trip to Jolene's while trying to figure out how to spend a day with nice weather and…read moreit definitely didn't disappoint. Ended up trying different wine flights and they had a lot of options that I definitely enjoyed. They occasionally have live music, and it sits right on the lake, which is definitely a nice way to spend the day. Ended up coming back with my mother and she loved the place Everyone was so nice and knowledgeable and I definitely felt right at home. Definitely think this is a good spot if you're looking for something chill to do on a nice day.

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Jolene Family Winery
Jolene Family Winery
Jolene Family Winery

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SummerWind Vineyard - Enclosed porch area

SummerWind Vineyard

4.5(31 reviews)
42.4 mi

My first-ever winery visit was to Summer Wind Winery, and it was everything I hoped it would be…read more I've always wanted to do something like this, and when my relatives came to town looking for something chill but vibey, my Uncle Daryl found the perfect spot. Even the ride there set the tone it was scenic & peaceful, and full of wide-open fields that felt like a refreshing change. It was the kind of drive that makes you slow down and just enjoy the moment. Once we arrived, the winery itself was stunning bold, beautiful. The wine selection was impressive, and I loved getting to explore different flavors. I figured out which wines I enjoy most, which ones aren't for me, and felt like I had a truly immersive first-time tasting experience. The staff at Summer Wind were amazing knowledgeable, friendly, and patient in answering my questions. Although I didn't get to order food this time, I saw plates coming out of the kitchen that looked absolutely delicious, so that's definitely on my list for next visit. I enjoyed myself so much that I'd love to make this a yearly tradition around this time of year. Summer Wind Winery gave me not just great wine, but a great memory, and I'll absolutely be back.

We visited SWV on a Saturday afternoon. The vineyard has beautiful views. Upon arrival, we were…read morecheerfully welcomed by the staff and presented with flight options. The pear sangria was refreshing. SWV offers a variety of food options which SWV freshly prepares upon ordering. SWV has indoor and outdoor seating. The outdoor patio is adorned with colorful umbrellas, tables and chairs with spectacular nature views. The indoor seating is adjacent to the tasting room and well air conditioned. We enjoyed the wine & food at SWV and recommend that you visit SWV for an enjoyable wine tasting experience.

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SummerWind Vineyard - Wine tastings

Wine tastings

SummerWind Vineyard
SummerWind Vineyard - Winners

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Winners

Chatham Vineyards - Non alcoholic drink from fridge

Chatham Vineyards

4.6(60 reviews)
73.0 mi
$$

What a beautiful drive in. Tucked back a few winding roads, and up into the long driveway you enter…read morea beautiful property known as Chatham Vineyards. We were warmly greeted and taking care of. We even had a little bit of history explained along with the process. We got an entire flight to try it all. It was nice! I cannot tell you if it was good though, because I don't really drink wine or well alcohol for that matter. But, the ambience and experience made it all great we had some nice giggles as we tasted. Overall it was a nice experience You can stay up to date on all things Chatham via their social media outlets and website. The little retail area is nice. A few items from local artists. A covered space or umbrellas to shade from the sun would be a great addition.

6 years later and this spot is still a fantastic little gem. After moving to DE we realized we…read morecouldn't get wine shipped to us, but now that we've joined the Chatham wine club, we have a quarterly excuse to spend the day roadtripping to the vineyard for a wine pickup. Over the years, this place has grown in staff (and production, it seems) but still maintains that local-ish feel for everyone who walks in the door. Grabbed our club allotment with a few of the classics thrown in for good measure: Un-oaked Chard, Rose and Cab Franc. Bring a picnic, grab a glass and let the pastoral views relax you.

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Chatham Vineyards - Surrounding wheat fields

Surrounding wheat fields

Chatham Vineyards - Tasting flight

Tasting flight

Chatham Vineyards - Great views

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Great views

The Williamsburg Winery - Tasty wine flight

The Williamsburg Winery

3.8(372 reviews)
30.6 mi
$$

Great local winery with plenty of seating, wine to choose from, and friendly service! On a weekday,…read moreit is pretty quiet and on weekends it gets pretty busy. There is seating outdoors, and plenty of space! You'll likely be met at the door by a friendly greeter - Nancy is amazing and helpful! Hopefully this winery gets a full food menu back, it's the only reason I took off a star!

My husband and I visited Williamsburg Winery during our Thanksgiving-week holiday and decided to do…read morethe 8-glass wine tasting. From the very first pour, we could tell the tasting was going to be generous and by the time we reached our eighth glass, we were definitely feeling tipsy. LOL We especially appreciated how the Winery has crafted its offerings over decades: from its historic vineyard on the Wessex Hundred estate to its reputation for elegant Virginia wines made with a strong sense of place. They offer reds, whites, dessert wines, and more. Along with our tasting, we did enjoy the charcuterie box. Now i will say that box was not worth the $22 paid. Everything was delicious inside; it was just the portion was tiny. In short, it felt like the perfect holiday outing: relaxing, indulgent, and charming. Also, the decor there was so cute and i loved all the Christmas decorations. We ended up buying five bottles to take home! If you enjoy wine and enjoy laid-back vibes on a winery estate, Williamsburg Winery is definitely worth a stop.

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The Williamsburg Winery
The Williamsburg Winery - Charcuterie board and raw oysters

Charcuterie board and raw oysters

The Williamsburg Winery - Wessex flight

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Wessex flight

Upper Shirley Vineyards - wineries - Updated May 2026

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