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    James Charles Winery & Vineyard

    4.0 (60 reviews)
    Closed 12:00 pm - 5:00 PM
    Updated 2 months ago

    Services - James Charles Winery & Vineyard

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    Wine is excellent! The view, the staff, the food all excellent. Very beautifully decorated for the holidays. I definitely recommend a visit to this winery.

    Cuvee' de la reine
    Jessica O.

    A great way to spend a Saturday is to pay a visit to James Charles winery! They're wine is very good, no weird aftertastes. You can tell quality is important to them. We first tried the Cuvée de la reine ($26). This is described as a mix of the Riesling and another wine with a hint of melon. We wanted a more sweeter wine to drink out in the sun and this one was perfect! Not too sweet at all, usually with a wine like this you get sick of it quick because it is too sugary but this was the perfect amount! We also tried their 1913 ($30). This was another great wine but this one was red. It has a hint of berry to it so a sweeter version but like the cuvée it also is the perfect amount of sweetness which made it another great one to drink outside! Something I also noticed is on the bottles they have suggestions on food to pair it with. A nice touch! We also loved the atmosphere here! They had live music, with a guy play guitar. There was a food truck but also the winery has a kitchen with food also. The building is so cute there is plenty of space instead but also a separate event space too. There is lots of outdoor seating and it's pet friendly! If you come and you really love their wines you can become part of their adopt a vine club which has lots of perks. You get exclusive wines and discounts on wines too!

    The front view from the parking lot.
    Tandis H.

    We came on a Thursday afternoon and it was quiet and peaceful - absolutely beautiful. The place is very nice, and so is the service. We were kindly welcomed to the bar area where we got an overview of the wines and tastings. We decided to go with a glass of wine so we could enjoy it on the outdoor terrace. I really liked the vibe out there - the furniture was nice and contemporary, and the shades overhead made the space feel light, area, and cool. Everything was perfect, and if you get the right spot you can even get a glimpse of the views beyond. Would be nice if someday they take more advantage of the views!

    a table set for a halloween party
    Nezu M.

    This is one of our favourite wineries! The wines were excellent- and I am very much partial to the Cuvee de la Reine! Fantastic company with Valerie, the manager.

    a glass of white wine
    Michelle D.

    Beautiful place to visit. Whites and Reds were amazing! Outdoor area has comfy couches and Adirondack chairs.

    Backyard
    Angel I.

    Beautiful space to wine down (and wine up!) and relax! Did a taste testing for about $10 each and the staff was very friendly and informative. Beautiful space to overlook the mountainscape and very cozy and trendy furniture. Good wine, too!

    White wine
    Breanne S.

    This is a beautiful venue with delicious wine choices! Complete with indoor and outdoor seating.

    Matthew F.

    Not bad for an opening day! Wine: 3.5 stars: JC served 6 wines for $10; 3 whites, and 3 reds. Some were little on the young side, but everything was OK to good. I really liked the tasting sheet descriptions; that was a nice touch. I also liked the diversity; not many wineries have red Zinfandel or dry Reisling, and they had both. On the minus side, everything was a tad expensive, especially given the more reasonable prices I see at other Shenandoah wineries. Facilities: 3 or 4 stars? Not the tasting-room extravaganza like I see in Loudoun county, but reserved and tasteful. I liked the garage-style door that opened up so you can enjoy the view; Shenandoah is a nice area so you can't go wrong with that. Service: 4 stars. This was opening day so they were busy but the servers seemed knowledgeable and friendly. According to my pourer, James Charles is owned by the same family that has the Veramar and Bogati Bodega wineries; apparently wine making is something of a family tradition. The grapes are from Veramar, which really isn't that far. I like Veramar a lot so this is a point in their favor. The Reisling was dry and crisp, and the Sav Blanc had the flavor of green apple. Dry Reislings seem to be rare in this area, so finding this was a nice surprise. Wasn't a big fan of the Viognier, though. The Reds included a "1913" Bordeaux style blend, a Petit Verdot, and a red Zinfandel. The 1913 needs time to age, but in time it should soften. The Zin was different; not being a Zin drinker I don't have any basis for comparison, so it was hard to rate. But I definitely liked the Petit Verdot. JC is about 1.5 hours from DC, so it's sort of a hike. But I think Shenandoah is an under-appreciated wine making region, so it's nice to see a new addition.

    a sunset in the back yard

    The wine and ambiance at James Charles was great! The staff (Alyssa, Raven, & Nino) were fantastic and very knowledgeable on the wine and provided great recommendations!! We cannot wait to come back soon. This is a must do if you're in Winchester!

    Miss Chloe
    Shawn W.

    Road leading to the winery Corvette friendliness is iffy. The winery views are ok. The tasting room is very nice. The wine pourer was very friendly. The wine 1913, was good and smooth, mildly tannic, fruit forward meritage, as the wine warmed up some licorice notes and plum came through. The southern style egg rolls very good ask for extra sauce, and the truffle fries are worth a try. Very nice French style winery worth a visit. SWaddell

    Elizabeth K.

    This four year old winery and building are modern barn chic. Wonderful bright green doors invite you to a panoramic view. Clean, slightly sweet whites and dry reds round out the tasting menu.

    Caren B.

    I'm so, so conflicted about this winery. First off: Winchester actually has a winery! Woohoo! But... I went on opening day, and I've gone again since, and I'll continue to go. But: the wines are kind of meh. They offer 6 wines, 5 of which are available to non-members (and the pretentiousness involved in a members only winery that doesn't even use its own grapes... well...). As with all young wineries (this one has only been open three months), the grapes aren't original to the region. The owners have another winery in Berryville (Veremar) that also imports its grapes, because wineries in this region just haven't matured enough to do their own thing. That's okay, but it makes them startlingly 'less than' the wineries in the Charlottesville - Afton region. That doesn't make it the worst winery (cough cough, Concord, cough cough, Stephens City...), but it just doesn't make it the best or the most okayish. The traditionally sweet wines aren't sweet, and they're touted as dry although what they really are is wet rock and fruit; the two reds are the Petit Verdot and the Zinfandel (which isn't a red drinker's red). Both of the reds are as of yet bland and lacking, but because there's no vintage prior to 2014 (The winery just opened in 2015), and whites are more forgiving, I highly suggest you go with the whites. My two favorites here so far are the admittedly acidic Viognier and the self-labeled "juicy" Riesling. Whites are always more forgiving of youth, and so I can only assume that these are my favorites simply because the reds are not mature yet. Don't ask about residual sugars, because they don't know: no matter how many times I've asked (several), the Sommelier doesn't know. They can't talk nuance, either; they know exactly as much as is printed on the tasting list, no more, no less. Tastings of the 6 wines (or 5, depending), are $10 per person. You don't get to keep the glass. (Pardon me for being a snob, but I find tasting fees distasteful, and against tradition, although I do realize that this is Virginia.) The scenery has promise: lots of promise. It's pretty now, it'll be gorgeous in a few years. The vines are young, and the hills are alive with the newness of construction and young trees. But seriously, in a few years this is going to be the prettiest winery in the area. This venue is full of potential, and the function room has lots of promise for events. The "members only" area is "exclusive" to over 200 people, and this place is only three months old. What that means is, IT'S NOT EXCLUSIVE. The benefits are: unlimited free tastings, access to one particular members only room, and an infinitesimal discount on quarterly bottle orders for pick-up (which is only really good if you like their wines enough to drink them at home, as opposed to tolerating their wines for the atmosphere). Frankly, I wouldn't purchase a membership here, because it would be admitting my tolerance for blasé wines to the world, while simultaneously gaining me access to a community of those that also apparently enjoy blasé wines. Come for the beauty and the tasting, but don't leave with a cellar's worth of $20-30/bottle meh.

    Tasting Room

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    4 years ago

    My favorite winery in Winchester! Staff is great and atmosphere is very relaxed. It's a great way to spend an afternoon

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    Thanks so much for your kind review! Hope to see you back again soon!

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    Page 1 of 2

    Ask the Community - James Charles Winery & Vineyard

    Are children allowed in the outdoor area?

    Hello! Children are allowed everywhere, in the tasting room and outdoors, as long as they're supervised.

    Don’t See Your Question? Ask Away!

    Review Highlights - James Charles Winery & Vineyard

    It has a hint of berry to it so a sweeter version but like the cuvée it also is the perfect amount of sweetness which made it another great one to drink outside!

    Mentioned in 2 reviews

    Read more highlights

    Heritage Hall

    Heritage Hall

    2.5
    (2 reviews)
    18.3 mi

    This place is beautiful for events and weddings. It is absolutely huge and gorgeous with a center…read morestage. You can use for birthday parties, weddings, and work trainings. I only gave it four stars because the onsight catering isn't the best. We only had salad, soup, and sandwiches which were alright but not outstanding. The dessert was cheap cookies from the dollar store but overall excellence experience

    I am very disgusted at the lack of professionalism and ethics run by this company. I have spoken…read morenumerous times with Sharon (Bonnies Butler's Gopher) about my renewal ceremony and initially rented both rooms. Unfortunately, I became very ill and couldn't continue with the planning of this event, nor the event itself. Setting aside the sadness I have from not being able to have that special day with my family, I had to cancel. We cancelled In December of 2014 and also were told it was no problem because another couple showed interest. GREAT!!! I had a friend ride by Heritage Hall and took numerous pictures of an occupied event hall. I waited for a refund, waited more than enough time. I contacted Sharon 4-5, maybe 6 times, she can only pass word from Bonnie the owner. Ridiculous!!!! I keep being told I will get a refund...when?! This doesn't sit well with me seeing she was paid from another couple for the same night. I know times are rough for people, but running a business in this fashion doesn't sit well with most. Piss poor ethics if you ask me!!!!

    Photos
    Heritage Hall
    Heritage Hall

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    Wayside Inn

    Wayside Inn

    4.0
    (62 reviews)
    7.1 mi
    $$$

    We had such a special stay at The Wayside Inn. From the moment you arrive, you can truly feel the…read morehistory! It's charming, cozy, and full of character in a way that's hard to find anymore. We stayed in Room 15, the Bernstein Suite, and it was incredibly spacious. The bed was so comfortable, and I loved the thoughtful details -- especially the cute vanity room with amazing natural light and the cozy seating area. The decor throughout the inn and in the room really stood out to me and was easily my favorite part of the stay. It felt like such a unique blend of historic charm and comfort. This stay was extra special for us as it was part of our 10-year anniversary trip while driving to New York City, and it ended up being the perfect halfway stop to break up the drive. It made the whole trip feel even more memorable. We also dined at Clem's Kitchen during our stay, and the food was great. (I'm gluten free and there were plenty of options!) I really appreciated that it's part of the inn, which made the overall experience feel seamless and convenient. Overall, it's the kind of place where you can slow down, soak in the atmosphere, and enjoy something truly special. I would absolutely recommend staying here if you're in the Shenandoah Valley area.

    Charming Place, Comfortable Stay…read more We enjoy stays at both chains and independent hotels/motels, just do a lot of research to ensure a solid, restful stay at either. This piqued our interest as the longest continuously run motel and it lived up to expectations of being charmingly quirky while also very comfortable -- plus, proving to be easy to access as a quick pit stop. Spouse & I agreed when checking out that we wished we were staying longer, to get to enjoy the surprisingly spacious sitting room and glassed-in porch -- we stayed in room #15 / Bernstein and recommend it to both couples and small families. The bed was cushy and my husband slept later than his norm, always a good sign for bed comfort. It is higher than average, so I took advantage of the provided step to hop in/out. Because the tavern is onsite, there were additional bathrooms handy downstairs when ours was occupied. As noted in our welcome sheet, water took a few minutes to warm up. So if showering and in a rush, run it first for 3-5 minutes while doing other prep. But hot water arrives and pressure was excellent. The rooms were spotless, though of course tiles and other fixtures are vintage and show age -- it's a historic landmark. We also wish we could have stayed longer to take advantage of the porch rockers and both the tavern or (intriguingly combined) Irish-Mexican restaurant on premises. There appears to be patio seating in back, so ask if it's associated with hotel or dining, if looking for other outdoor space. Indoors, there are public spaces (two parlors plus other spots -- it's a rambling building!) with books and a checkerboard handy. Maybe more amenities but we ran out of time to explore. It's not a B&B -- there's just a stocked Keurig in the lobby and some packaged snacks and bottled water (free but donations welcomed). But if the Tavern is closed, as it was on our Memorial Dat visit, there's a small coffee shop just a half-block away, serving breakfast late as well as some sandwiches and bowls, plus good teas & coffees. Incredibly friendly staff. Looked like a few other dining options nearby plus historic sites and walking trails. We arrived very late, and management is not onsite at that hour, but instructions for arrival were provided, comprehensive and very easy to follow. Staff on site in am were very pleasant and helpful. Tip: If arriving late & lugging a ton of luggage, ask which rooms are closest to the late-night entrance. Number 15 is on the far side and up a flight of stairs -- fine for us with just overnight totes & computer bags but just something to keep in mind if you have a lot to unload. Overall, an enthusiastic thumbs-up. It looks like it would be a fun, relaxing hub for a weekend escape. But also great as a highway stop, as it is just a few minutes' drive from the exit.

    Photos
    I have no idea who that is.
    I have no idea who that is.
    Jubal Early (Room #1) - This is perhaps the Inn's most historic & best room. A dozen or more Civil War Generals stayed in this room.
    Jubal Early (Room #1) - This is perhaps the Inn's most historic & best room. A dozen or more Civil War Generals stayed in this room.
    The Wayside Inn!

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    The Wayside Inn!

    James Charles Winery & Vineyard - wineries - Updated July 2026

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