Incredibly gluten-friendly!!! Was also able to accommodate my dairy allergy with a veggie side (no gluten-only fryer) instead of fries. I wish I could remember our waiter's name! We were there Friday, October 2, in the three-person booth, the cozy room with the brick fireplace. He was spectacular, and patient, with my needs. No judging (to my face at least) The food was GLORIOUS. Ohhhh my word Oysters with mignonette, mushroom caprese (polenta on the side), I had lobster roll on gluten free toast points, my friend had the fish tacos (& couldn't finish them- so much food), my husband had the bone-in steak (which was unbelievably perfectly seasoned & melt-in-your-mouth delish). Every single thing was FABULOUS! We will definitely be back!!! Thank you so very much, Village Square, for allowing gluten free to be so easy & fun for once read more

The food was amazing--expensive, but genuinely amazing. I had the lobster roll, my friend had the summer salad with salmon, and we each had two drinks. The bill was about $120, which felt reasonable for the quality of the food. Unfortunately, the service really brought the experience down. Our server was clearly overwhelmed and had far too many tables. She was perfectly pleasant and seemed to be doing her best, but it took about 20 minutes before we could even ask for unsweetened butter for the rolls. The butter they initially brought was so sweet it tasted like buttercream frosting, which was not at all to my taste, and then it took another 10 minutes to actually get the replacement. I really wanted to love this place because the food was excellent, but this was a Monday evening. If the restaurant is this understaffed on a Monday, I can only imagine how much worse the service is on a busy weekend. As much as I enjoyed the food, I don't think I'd go back. read more

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Village Square is in a beautiful spot in Old Town Winchester. We sat outside on a great evening with music nearby, people strolling past, shops and ice cream all around. The setting is genuinely charming, and our waiter was excellent, friendly, attentive, and clearly trying to guide us toward the better choices. The Peruvian Tuna Ceviche was one of the real highlights, although to me it ate more like a tuna tartare. Fresh, bright, and very good. We finished every last bite. The blueberry dessert met the same fate, and those were basically the two plates that could have gone straight back into the cupboard. Unfortunately, that was not true of most of the other dishes. The Old "Quack" shioned, a duck fat washed Old Fashioned, sounded clever but did not work for any of us. I love duck and I love bourbon, but combining them only proved that two things I enjoy separately do not automatically improve each other. Some relationships should remain strictly platonic. The Blackened Shrimp & Grits had very good shrimp, but the presentation was messy and the dish never really came together. I had the Seared Heritage Pork Chop, which came highly recommended. I love a good pork chop, so I really wanted this one to work. The potatoes au gratin were excellent, but the sauce was overly rich without much depth or flavor, and the pork itself somehow became the least interesting part of the plate. That was disappointing. Lovely location, excellent service, and a genuinely pleasant place to spend an evening. Unfortunately, the food was too uneven for the price, and I am not sure I would return. read more

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Delicious food with no wait on a (rainy) Friday night in Old Town Winchester. The duck and seafood chowder were perfection. Highly recommend for a slightly upscale, yet still relaxed evening out. read more

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We came out for the Father's day Sunday brunch special and was not disappointed. He opted for wing app and I the oyster. Flavorful oysters and wings were crispy and meaty. Not pictured is the fabulous shrimp and grits I devoured. It was rich yet very well balanced and seasoned. They were extremely busy but our server did warn us ahead of time. We were in no rush and someone was enjoying the Mimosas too much to care lol read more

Village Square - oysters - American Near Me - Winchester, Virginia

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Mostly ignored by staff. 45 minute wait for food that was not cook and tased bad. No one said sorry or even cared. Left a 50 cent tip.

Came here for a big birthday lunch (there were like 14 of us) and got the private room, which was perfect. Staff was attentive and nice, accommodating to all. Food was delicious, and the drinks were even better! read more

Village Square - Fall themed Margarita - American Near Me - Winchester, Virginia

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Food and service was very good. Ambiance was a bit loud, despite the fact that not all tables were occupied. Oysters were delicious but many had grit which was disappointing and ruined the experience a bit. Their mignonette was a delicious condiment though. The crabcakes were amazing! And the venison loin with apple stuffing was great too. read more

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I have never felt so disrespected at a restaurant. I've been here multiple times, and every time (except one occasion with bad service in which I still tipped) I've always tipped 20%. During my most recent visit with a friend, we noticed an automatic gratuity added to our bill -- for a party of two. When I asked why, the staff told us it was because we had been there "multiple times without tipping." That was completely untrue. My friend, who had only been once before, had also tipped 20%. When I asked them to provide proof with past receipts, they said they would but never followed up -- despite me calling over five times afterward. Instead, they felt comfortable insisting we didn't tip, without any evidence. It was clear this assumption was based on how we looked, not facts. Being falsely accused, having someone else's behavior attributed to me, and then brushed off when I tried to address it was humiliating and dehumanizing. Even after I asked to speak with the GM, all they offered was to remove the gratuity, which completely missed the point. This felt like racial profiling, plain and simple. I will not be returning, and I want others to be aware of the treatment we experienced here. read more

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Service was superb! Food was extraordinary. Unique desserts. Parking immediately behind.

I was in the mood to eat outside on my first visit to Winchester. Service was impeccable and I ordered a glass of house wine and a lobster roll. It was delicious and I would definitely order it again. That said, after tax and tip, it was a $50 lunch. read more

Village Square - Lobster roll - American Near Me - Winchester, Virginia

We were immediately seated outside and in the sun as requested. The smells around us we're wonderful and the looks of the meals coming out the door were great. I ordered a 1/2 dozen oysters ($1 special) and the pot roast French dip. The oysters were fresh and sweet. The fit and ember was a tasty drink with a hint of vanilla. The French dip was amazing...the meat was so tender it practically melted in my mouth and ohhh the gooeyness once dipped into the Au jus. The fries were crisp and tasty as well. She ordered the lobster roll. Not what she had expected, kind of a lobster salad on a hot dog bun, it was a little bland allowing the bread to be the star vice the lobster. She felt the fries were the bomb. It was a great day to sit outside. read more

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The server was very nice. We ordered an appetizer that came out after our meals came. The food was just ok. Any place that serves shoestring fries doesn't rank in the 4.4 star category (per Google reviews) especially for a place that serves a $50 steak entree. Probably the best deal here is the shrimp or crab legs. Not overly impressed. read more

The Sunday Brunch is phenomenal, everything you could possibly want and more! The fried oysters are incredible read more

Village Square - Patio arena - American Near Me - Winchester, Virginia

Was on business and ate here 3 times Food and Service (Janelle) were outstanding Raw oysters at Happy Hour such a great deal ($1/per) Great Ketel up with BCO's read more

Village Square - Oysters on the Half Shell - American Near Me - Winchester, Virginia

For the last couple of years, our work team has come together for a wonderful Holiday dinner at Village Square! This time, the 5 of us were able to sit it the super cozy back room with fireplace. Service was so incredibly friendly and attentive. Jackson was great! We ordered apps of raw oysters, shrimp and calamari! All were fantastic! So many delicious mixed drink creations to choose from. We had several. Our entrees included the specials, along with crab cakes, filet and salads. Everything was cooked perfectly! This is a great spot with a great menu, not overwhelming, with excellent options. If you haven't, check them out!! #deitzeatz read more

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Tonight was our third time trying Village Square and it's been underwhelming every time. The service was great and we love sitting on the patio. The food just isn't very good. I had the "sandia salad", there were four chunks of watermelon and one slice of grilled jalepeno. The dressing did not go with the salad at all. Same with my mom's caesar. We shared an order of the sugar cane shrimp and it just didn't have much flavor. Everything was drenched in the same sauce but it was kinda bland and for shrimp skewers I'd expect them to be cooked more. It could just be my palette, but there is nothing on their menu that has me wanting to come back. read more

Went on New Year's Eve 2025. I had a rockfish special and my wife had blackened shrimp. Both were terrible. They must have a new chef because we went last New Year's Eve and the food was terrific. In addition, this was our waiter's first night on the job. He dis OK, but the service wasn't great. I don't think I want to return. read more

Stopped by with a coworker tonight. We both got their special, which was an 8oz flank steak with asparagus and potatoes. Our meal was tasty and our server was attentive. Would return in the future. read more

Village Square - Flank steak,asparagus, and potatoes - American Near Me - Winchester, Virginia

We frequent Village square and always have the best service and experience. Yesterday we tried the new Happy Hour Menu and enjoyed everything we tried! The margarita Tower was fresh and delicious, you could choose from Original, Strawberry, coconut, blackberry and peach. between our group we did two blackberry , a peach and a coconut and they were all great! The atmosphere is always great and the staff is always very friendly and attentive read more

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village square okay. our waiter hanna was so cool when we met her. perhaps she is the only one doing outside tables but we got here 7:20pm. our drinks did not come out till 7:59pm. we did not have silver ware, had to ask the busser. the busser is working so hard, we saw him 3x more than our actually waitress. his name was david we got to know him. i feel bad asking the busser/runner for items but we did not see our waiter in such a long time we had to. after the drinks came we finally put our order in ffood almost 40 minutes after we have been sat. now its is 8:30pm and im writing this review because its been 35 minutes since and our food has not come out. when i got my drink (ipa beer) it was too warm, must've been sitting out for at LEAST 15 minutes. I went back in to get it re-poured and the bartender gave me a look and said it would come out the same. when i tasted it, it was ice cold. inside was not too busy so i am just disappointed in the service. i could go on, but im writing this review while waiting for our food/ second drink to come out. point is, service is very slow. waitress is sweet. perhaps there are not enough workers but it's not even busy tonight so, that is my speculation. will continue with the food once it's come out. food came out hot. salmon and asparagus were salty. duck was salty. pretty much everything had too much salt. ah- not a big fan. read more

This restaurant has become our go-to spot for most meals when we're at Loudoun St. Mall. If you're in the mood for crab cakes, shrimp, salads, soups, or a burger, you won't be disappointed. The daily specials are always fantastic! They also offer a great selection of beers, wines, and drinks, along with a special Sunday brunch menu. Stop by--you won't regret it! read more

Great American bistro on the mall in Winchester. Reservations process was simple and easy. Service was prompt and friendly. Doz oysters, wedge salad, butternut squash soup, NY strip, and scallops. Everything was fresh and delicious. Definitely a solid choice! read more

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We were VERY disappointed in our experience at the Village Square! It started out well, with our group of seven having our own separate room. The two of us who arrived early were seated and a basket with a few slices from a baguette were provided along with a the equivalent of two pats of butter. When the other 5 people in out party arrived, a water container with a crack was provided. By the time the server had returned to take drink orders, the table had a huge puddle of water and were had used all of our napkins in an attempt to clean up the mess. When the server returned with the drinks, we had to ask for another pitcher without a crack and additional napkins. Our dinner orders were taken, but it took more than 90 minutes for our food to be served! No bread was provided for the other end of the table. They were out of several items on the menu, and it appeared they were rationing other items to ensure they didn't run out. For example, there were 3 scallops and two spears of asparagus on one main dish, and the stuffed flounder had very little of the listed stuffing items. All entrees were cold by the time they were served. No mention was made of the birthday we had mentioned in our reservation, and a cash discount which had not been mentioned was on the check. Had we known, we'd have stopped by the bank and picked up cash! The 20% gratuity was calculated on the after tax amount and automatically added. We paid our bill and departed for another venue to ensure all members of our party had enough to eat! read more

Had the pleasure of going to Village Square in Old Town Winchester for my birthday dinner. To start, I think this is the only thing close to a high end restaurant in Winchester. It has been the only one I've found. If you know of others, let me know because I love great food. The restaurant has two sides. Looks like two store fronts were combined together. What I thought was kind of cool was there are a whole lot of cloistered sections which makes for an intimate atmosphere. My party was on the side with the fire place which was really cool. We needed reservations because it was a Saturday night. And I would definitely suggest getting reservations because the place was packed when we arrived at 7pm for dinner. The service was really great and they catered to our every need. I am kind of a beer Snob and I ordered a craft beer that came with no head which is a red flag for me. I asked for an extra glass to re-pour my beer and my server brought it with a straw. When I asked him what the straw was for he showed me a neat trick of stirring the beer with the straw to make the desired head. What a fantastic idea. Didn't even need the glass and now I have a great life hack. That alone was worth the visit here. So onto the food which was amazing. Our dinner was all seafood and they do is quite well here. Started with a seafood platter, please see the pictures for description. For the main course we had two orders of scallops and the cordova special. Haven't been that full or had my belly that happy in a long time. Had dessert as well, but I don't remember what it was. My dessert was Bourbon. Village Square has an awesome selection of spirits, especially whiskey, Scotch and Bourbon. I will definitely be returning. Wish I could eat here everyday, but It is pricey and I would be broke in no time. If there is one place in Winchester Virginia to go for that special occasion, I would suggest Village Square. You can't go wrong here. You will make memories to last you a life time. read more

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This restaurant never fails us when we are visiting Winchester. We ducked into a cozy seat at the bar with friends for dinner (our friend, Gene, knows everyone there.). We had cocktails and wine and then ordered dinner. Food (5/5): We had the duck for dinner and it was fantastic. Medium rare with a southwestern black bean/corn and tomato sauce. A bit odd for duck (usually it's orange sauce) but overall, it was prepared well. Service (5/5): Great, as always! Atmosphere (5/5): This place was packed on a Saturday night. It was really great to see people out and about again! read more

Village Square - Duck (medium rare) - American Near Me - Winchester, Virginia

We went for brunch this time. I know I said I wouldn't return, and if it was up to me, we wouldn't. But our group is too big for any other restaurant downtown, so we had to go here for brunch on Easter Sunday. Portions & Price (1/5): Again: small portions, low flavor, over priced. This is the 4th time I've been here, 3rd time for brunch. They raised the normal brunch price to $38.50 a person. This includes an small appetizer (soup, salad, or bruschetta), an entrée (a ribeye option, then the rest were seafood or mushroom based), and a dessert (cheesecake, flourless chocolate torte, and a limoncello cake.) With every course, you get a mimosa (so 3 total for the $38.50 price). The mimosas come in a flute glass so it's extremely small. They're about 4 sips and the drink was done. Because of that, some people went through all 3 of their drinks before the appetizers came out (40 mins after ordering). After the 3 that come with the meal, it's $2 for each additional drink. Appetizer: I got the salad. It was onion packed, but the walnuts helped the flavor. Entrée: I got the ribeye with asparagus and potatoes. The ribeye wasn't seasoned; there were 4.5 pieces of asparagus, and a handful of halved potatoes. Dessert: I got the flourless chocolate torte. This was the only good thing. It was very dense and rich. Drinks: I got the lavender grapefruit mimosa. It was ok. Service (2/5): We got a waiter that was extremely slow, yet everyone got what we ordered... no mistakes. The wait time for the food though was insane. It took them 40 mins to get our appetizers out, then an additional 20 to get our entrées out. The waiter didn't know their drink menu well, so he had to keep going back to the bar to see if he could do that: Bloody Mary but with tequila instead of vodka. When asked for hot sauce, the waiter brought out a bottle that has 1 splash left in it. We were all laughing at how crazy it was to serve that instead of throwing it out/refilling it. I'm not a fan of this place at all. read more

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Our waiter, Jeffrey, and the team at Village Square are tremendous! We went here for our three year anniversary and Jeffrey went above and beyond to take care of us. We ran into some unforeseen pre-dinner cancellation from The Wine Room at Taylor Pavillion, by absolutely no fault of the team there. The Wine Room and The Village Square partnered together to make our night truly memorable. I can't give enough compliments to Jeffrey either! His hospitality, recommendations, and service were best in class. read more

Great local gathering place. We really enjoyed the menu change. The stuffed flounder was a delicious entree as was the oysters as an appetizer. One of our party enjoyed the shrimp and grits. He reported the chowder was flavorful and meaty. The service was attentive for our needs and very friendly. read more

It was my first time visiting both the city and the restaurant, and I couldn't have asked for a better introduction. I thoroughly enjoyed my walleye dinner-perfectly cooked and full of flavor. Sitting outside in the fresh spring breeze made it even better, with the added pleasure of people watching and soaking in the lovely view. A truly relaxing and delicious evening. read more

Village Square - Pecan Crusted Walleye with rice pilaf & asparagus - American Near Me - Winchester, Virginia

Passing through the area on a Sunday and wanted a lunch stop that wasn't highway fast food. We didn't have a reservation but could get a seat in the bar area off the pedestrian mall side which only offered the 3-course fixed price brunch. So, we went for it. LIVED the fried green tomatoes! Sooo good! Had the salmon with risotto as a main and it was excellent. The asparagus that came with it was nicely prepared as well. My co-traveler had the eggs Benedict with grilled potatoes which she said was also really good. We were too full for dessert but since it came with we got a lovely piece of chocolate torte and a slice of lemon marscapone cake. These were sooo good, even the next day after riding in our car for many more hours. This would be a 5-star review except for a couple of things. It was difficult to get attention from our server. We ultimately just gave up on getting salt and pepper. We managed to get a drink refill from a different server. My spiuse used the ladies room and there was no TP so she mentioned it and someone came to fill it. I went in maybe 10 mins later--- no paper towels. And the light had been flashing when my spouse was in there the first time. As a one stall bathroom, especially during a pandemic, that wasn't great. We also soooo wished we could have had 'real' glasses for our iced tea and sodas. They had some sort of cheap drink special for brunch (alcoholic) so they were making these up a few at a time in clear plastic solo cups. I get it... but we weren't having that so would have enjoyed our nice meal with a decent glass. Oh well. Good food though! read more

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Four of us met here for dinner on a Saturday evening. It was a great meal with good service. They have a pretty good wine selection as well as a good variety on the menu. My wife had steak and lobster and I had the salmon. Both were excellent! It is not an expensive dinner, but for the occasional pricey dinner out with friends, this is a great option! read more

Village Square - Inside view - American Near Me - Winchester, Virginia

I had a fantastic birthday dinner at Village Square! The food and service were top notch and we will definitely be dining here again for sure. I highly recommend Village Square! read more

Awesome fresh oysters, succulent and sweet! Caesar salad was very good and came with 3 pieces of anchovies which made the taste even better as originally intended! Servers are friendly and brought a bowl of chilled water for my pup Tucker which cooled him off as the high temp weather was almost on the uncomfortable side- it was refreshing!!! Will come back just for oysters and when we actually did come back 2 weeks later, unfortunately they were out of oysters; thus, the 4 stars instead of 5. Worth checking back next time in this area. We chose outdoor seating because of pup in tow who enjoyed his bowl of iced water! read more

Village Square - American Near Me - Winchester, Virginia

Great service and good food. We had fried green tomatoes and fried oysters. Yup, that's what you do when in the south, eat fried things. The batter on the tomatoes was a little thick and the batter in the oysters could've been slightly more salted. All fixable issues. The service was great! read more

Village Square - Fried green tomatoes. - American Near Me - Winchester, Virginia

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Old town style street in the heart of Winchester Virginia. Stopped by after a wine tasting for dinner. I started with the watermelon margarita with black lava salt. I worried it would be too sweet but it was well balanced perfection. Dinner was the 6 oz filet with potatoes and asparagus and a glass of red wine. My filet was cooked to a perfect medium rare. I ate every bite of my meal and would recommend to anyone passing through! read more

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Ambiance, food, service perfect. Drinks are great and our son loves his special bourbon. Like the happy hour drinks with dinner. read more

Pretty good. We came here for a rehearsal dinner for my sister-in-laws wedding. The food tasted good and I was filled by the end of it! The portion size was dependent on what you ordered off the fixed menu. For example, the fish plate that I ordered (in my pictures) was wayyy smaller portioned than the steak dish that other's ordered. Regardless - I was full, satisfied, and enjoyed my chocolate mousse cake at the end...yum! read more

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Happy Hour is Monday-Friday & starts at 4pm. $5 draft beers & a Happy Hour menu that features $1 raw oysters & $10 for 1 lb of spiced tail-less steamed shrimp! The wings are bone-in & are awesome too! Large selection of whiskeys/bourbons as well. We always sit in the back by the bar. Additionally, the waitstaff are friendly & attentive. Do not miss out! read more

Had such an amazing meal - per usual. But a 3.5% card fee?????? I have not seen a restaurant with that high of a fee if you don't pay with cash. Just disrespectful to put that on the consumer. read more