Great food and d atmosphere, French dip is awesome, will definitely go back jesse was a great server

It was Valentine's Day and we were looking for a nice dinner...saw the sign out front showing stuffed grouper. The ambiance and food was absolutely amazing. We really enjoyed our dinner. read more

First time here in years. I just never think of it as a option in greenbrier for some reason. I came in and was immediately greeted warmly by my server, Casey. It's basically a old bar but it's been kept up decently. I ordered the French dip. Can not say enough how amazing it is. They make it on-site and it taste that way!! From the meat itself to the aus ju. GO GET IT !!! read more

Winston's Cafe - Prime rib sandwich - New American Near Me - Chesapeake, Virginia

Still love this place. Welcoming to carpet baggers. Great food. Awesome staff. Incredible locals!! What more can u day for?! read more

Winston's Cafe - Monday Special: the $6, 1/2 lb burger. Buddha hands - New American Near Me - Chesapeake, Virginia

Very nice, comfortable place with tasty food. The waiter was very personable. Dessert was sinful and delicious

Awesome service and great food! If your looking for a relaxed atmosphere and affordable you should definitely check them out

Was here a few months back and the food was great. Today, everything was cold. The French onion soup was tepid and you could tell they used a torch instead of a broiler to melt the cheese. The bread was cold underneath. They forgot my salad. When I did get it, there was no dressing. Just a big piece of blue cheese. I got the Surf & Turf. Which was cold. The crab cake was supposed to be broiled. Instead, it was microwaved... and cold. I sent it back and when it came back, the steak was stone cold! Brrr! Sorry Winston's. read more

Amazing service; friendly, quick and attentive! The food--- delish! We had the French dip and the walnut cranberry chicken salad. Both were full of flavor and an awesome portion! Great job Winston's cafe!!! read more

My favorite was the tuna wrap with fries. The reason I took off a star is because they charge for every little thing. Mayo $1 pickle$1 onions on burger $1 tomato $1 lettuce $1 fries $2. So when they ask you if you want any of these things with fries. make sure you know your 10 dollar burger is going to end up being 16-19. Won't go often but the food is pretty tasty. The other star is for consistency. One chef cooks a meal amazing. The next is something I could have done on my own. Staff is nice and friendly. If you want good food this is the place. But if it wasn't great try them another day at another time and you'll know exactly what I'm referring to. It will be amazing. read more

Wouldn't feed the food from there to a stray dog. I could have played hockey with the cheeseburger they served me and my wife.

Weekday around 2pm Walked in confused because I missed the PLEASE SEAT YOURSELF sign. After walking to the back without being greeted, I walked back up to the front and saw the sign. No booth or table seats were available now. Sat at the bar. Dislike. Seat to bar height ratio was very uncomfortable to me, either bar too high or seats too low. But seating may be perfect for a 6ft dude or dudette :-). Surveyed the restaurant once again and found a seat at a high table. Yippie! I have also been handed a menu. Yippie again. Menu difficult to read due to the glare from the overhead lighting on the type of protective sheet covering. My seafood quesadilla was great. Delicious. Yummy shrimp. Came with sour cream. Serving size was satisfying. I can see myself ordering the seafood quesadilla to-go In the future. Servers were nice, but super busy. read more

Winston's Cafe - Seafood quesadilla - New American Near Me - Chesapeake, Virginia

Awful, just awful. Ordered from grubhub. Crab cakes were 80% filler, the mashed potatoes tasted old like they weren't covered in a fridge it had a weird after taste. Oh, and they didn't include my salad. Never ordering from here again. Gross read more

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Nice & quaint, local spot that has a grown quite the following for a pretty awesome band by the name of "Ruckus in the Papers". Good drink prices. Service is pretty good. You can tell there are nice serving of regulars. I remember having a crab cake here that was actually amazing! Also, this place has Lumpia FTW! Unfortunately, I think it's a little too tight for musicians but this can also be seen to make the experience more personal. Can't wait to come back and experience it more. read more

Winston's Cafe - Those specials - New American Near Me - Chesapeake, Virginia

We decided to try Winston's! I ordered the crab cake Sammy and hubby ordered the NC pork bbq sandwich. They were both good and so were the fries! We also ordered the mozzarella sticks. They tasted like they were frozen from a box but the rest of the food seemed fresh. My only tidbit would be the atmosphere. It was a warm Spring Wednesday afternoon. The restaurant wasn't busy at all. Outside seating would be nice. I do get the vibe that maybe it's a sports bar like place with the TVs all along the wall. The lights are super dim on the inside. The restaurant is very narrow and tunnel like. It gets darker the further you go back in the hole. * (I lied, I have two tidbits) the "please seat yourself" sign isn't very welcoming. This was our first time + it looks like a dark cave. Maybe some bells on the door to know when guests walk in or even a host/hostess. Our waiter was nice and attentive. I was torn between the crabcake and seafood quesadilla. He didn't have much input or advice on what to order/people's favorites but it's okay. I get the vibe that it's family owned. Overall 3/5. read more

Arriving in Chesapeake, late, on a Sunday night, is not the easiest way to get fed. Luckily, we Yelped to see what was open, that had great reviews, and we stumbled upon Winston's Cafe. So glad we did. I was bummed when we learned we were too late for the full menu but that quickly vanished when we saw that the late night menu had .59 cent wings. Yummo! Our server, James really took care of us with all flavor options and great recommendations. That, coupled with the cheesy bread, was all I needed and more. Literally more... I ordered two orders of everything. Now We're back here on a Monday night, and our server, Frankie, is hooking us up with the special drinks - this place is a hidden gem! read more

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this was our 1st time dining here. we had a table of 3. all 3 of us ordered a different meal. I must say, we were all amazed! the food was prepared & served to perfection. cheeseburger, chicken sandwhich & club sandwich. the fries golden & seasoned. the service was wonderful. they never made us wait. they checked on us often. All the ladies made sure everyone in the entire establishment were good. the ladies worked 2gether to take care of all the customers. this could be our new favorite restauran! read more

I came here for the first time tonight and it did not disappoint. I've driven past here many times but have never stopped. I'm not sure why I never did, but I wish I have before. My parents had been here before when they used to live in Greenbrier when the restaurant first opened but hadn't been in years. We decided to come to Winston's on a whim because my dad knew he wanted steak. There were many great decisions on the menu that my dad started to second guess if he wanted steak. He did get the black and bleu ribeye which came with a salad and a side. I ordered the crispy chicken wrap and a side of fries. The best part was the brownie sundae at the end. My dad said if he was on death row this entire meal would be his last meal. Our waitress Jacqueline was very attentive and friendly. Before we left the owner came around and introduced herself. I will definitely come back here soon! read more

Love this place. Very friendly crowd, outstanding food, live music, had the rockfish with citrus sauce, zucchini and garlic mashed potatoes. Really, really good. Frankie is the best behind the bar, so friendly, sociable and cute. My go to place when in Chesapeake!!! read more

Winston's Cafe - Joey Wood, exceptional guitar player - New American Near Me - Chesapeake, Virginia

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We really wanted to like Winston's. The service was good but the food was not. My husband ordered the English Dip because it was chewy and way overcooked. I got the chicken wrap and it' was awful. Opened it up to see why, the bacon was literally black as charcoal. Up charged for fries but they weren't edible, I think the fryer needed to be changed. read more

I had a salad which was a little wilted and brown. I also had muscle appetizers which were different having pasta and cheese in with muscles in the shell. The flavor was good. I would definitely have that again if it was on the menu daily. read more

I've been to this place twice. Both times I got the Winston's burger. The first time with the bun and the next time without. The first time the burger was perfect! It was juicy and all the different flavors just melted together. The second time it was overcooked and hard as a hockey puck. I actually took a few bites in an attempt to "eat around the bad parts" but couldn't handle it. So I sent it back. When a new burger arrived, it was much better and I actually enjoyed it. The inconsistency is the reason for the three stars. Seating is also a bit limited but I totally understand that is something that can't be helped. It's just something others might want to know if they are planning to go. read more

Great place! We love Franky the barmaid, she's fun and very attentive . The wings, burgers, salads and nachos are the bomb!! Drinks are well poured and the prices are great. Do your self a solid and hit this place tonight. Great place . Heading up tonight for Restaurant week. I am excited for 3 course meal for $20! read more

Great local bar and restaurant. Food is above average, and service is very good. Nice location in greenbrier.

Here for work about a year later. So impressed last year, made it a point to get back on PRIME RIB WEDNESDAY! Did NOT disappoint! Seriously y'all, gotta go! I'll go back every time I'm here! read more

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Good food good prices & good service - entertainment during week & weekends. Karaoke and live bands

This is my favorite place ever. My boyfriend and I met here two years ago and we still come at least once a week, if not more. The staff is so friendly. The food is amazing! It's such a laidback atmosphere where everyone knows each other. Live music, game nights, karaoke with DJ Kellie whom we love! You got Frankie, Nate-Dogg, Colby, Ms. Tracy among others! Winston's feels like home and never lets us down. Whether it's a casual lunch or a late-night party, this is the place to be! read more

Food was pretty good but that's not the reason for my rating. Everyone that works there are excellent and friendly. Service is about average speed. My complaint is when I was brought my order initially, I was brought the wrong food no biggie. They ended up bringing me the correct food. BUT!!! I watched as the server placed the first order back in the window under the warming lights and not even 2 minutes later deliver that same plate to a gentleman and lady on the other side of the bar. This was just unsanitary and I think it should be pointed out. I let the gentleman know but he didn't seem bothered so I guess all is well that ends well. read more

The servers were nice. The place needs a good cleaning. The ceiling looks nasty. My crab cakes were soggy

it is an understatement to call this place a hidden gem. The food was the best I've ever had from any restaurant. everything was a 10/10 and had so much flavor. the customer service was so good as well as the environment. i highly recommend read more

Service was 5 stars but the food was terrible so I am averaging out at 3 stars. Worst crab cake I have ever had. Best ranch dressing ever. Great cocktail so I would go for drinks only. read more

As always a dynamite meal with outstanding service!! Black and blue ribeye is amazing and the pistachio cheesecake .... I cannot for the life of me understand why folks would eat at the Ruby Tuesday next door to this gem!! Thanks Megan!! read more

Ahi tuna wrap with awesome green beans. Love this place! Not only is the food fresh and reasonably priced, it is also delicious and the staff is friendly and accommodating. I love that it's just the right size and you feel like family when you walk in. Parents- they are awesome with little kids too!! read more

Winston's Cafe - Green beans and ahi tuna wrap! - New American Near Me - Chesapeake, Virginia

Winston's is really starting to turn into our go-to spot for a great meal or an after work adult beverage. We've been here quite a few times since the office moved to Greenbrier and staff have really taken a shine to us. They know what we like, food or drink, and are just extremely personable. Last Friday evening I joined co-workers here and ended up staying for dinner. I want to point out, in case I haven't previously, that all of the beers on the menu are Virginia beers and the beer menu is pretty extensive. I've really enjoyed the Devil's Backbone Vienna Lager of late. Food portions for the price is excellent and most nights they also live music. Nothing loud or crazy, just acoustic and it's pretty cool. You should definitely check them out if you're looking for a good locally owned spot in Greenbrier. read more

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First time here..Great service and drinks are just right. Food cooked to perfection!! Will, the chef is the bomb!!! Ask for his service!! The evening chef Darren doesn't have the technique of cooking. Wasn't satisfied with the food and he didn't even come out to fix the issue. The tuna and steak bites came out overcooked, unlike when Will fixed it!! Our first order from Will came out to perfection, therefore we ordered two addition orders! Second order that Darren fixed came out overdone, no lettuce and sauce splattered all over the plate. Looked like a five year old fixed it. No attempted rectification from Darren, but will overheard our conversation and immediately fixed the issue and his shift was even ending! Waitress and bar manager were very personable. Overall good atmosphere and food. Just don't get Darren to cook it!! Will try a second time. read more

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Great service From our bartender Casey, even with one leg she ran the whole without a single problem! Highly recommend!!

It's a bit rundown inside. Like, there's duct tape on the seats in booths that are already problematic because they're sunken in. But it is a bar, afterall. And it's a decent lunch spot. We both had the potato soup, which was good even though it was a little thinner than I'm used to. My date also had a half of some type of sandwich that was very filling and appeared appetizing. It was a cheap and quick lunch, so I'm going to add it to my rotation. read more

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my boyfriend and i stopped by and i am so glad we did! total hole in the wall, but super good! i got their crab cake sandwich and it was amazing! their fries are super good too. try their jalapeno margarita! and make it a jumbo!! the service was awesome, the food was fantastic, and they were fast! next time, i'll have to try their dessert! read more

Me and my boyfriend decided to give this place a try since the yelp reviews were high ! Omg we loved this place. The service was amazing and everyone here was super friendly. This place has karaoke the night we went and upon entering the restaurant we sat our self. A few seconds later the manager came over and gave us menus and we gave drink orders. I order a strawberry lemon martini and it was delicious. The food was great too. I would definitely recommend this place for a chill date night or outing with friends. Next time we are in Virginia I would visit !! The only reason why I gave his place 4 stars was because the menu was limited and I didn't see any desserts listed for my sweet tooth lovers. Great place overall though. read more

Winston's Cafe - New American Near Me - Chesapeake, Virginia

Prime Rib Special Wednesday night $16. Excellent ! Tender & cooked perfectly, Med-Rare. Mash potatoes ok. Side salad was good, served on a cold plate- nice touch. Service was excellent. My waitress was also the Bartender- I was seated in the back , close to the Bar. A little noisy. Seems to be a Locals hangout. Good Times. read more

First impression is it's not a bad looking place. It is kinda dark on the inside and the lighting isn't choice. There were no bright upbeat colors. But it did look nice for what it was. Only a fluorescent bulb to light up the tiny table. The table wobbled too, so there's that. The waitress was nice and friendly. I ordered the pick two for $5.99. With a side of fries as an addition. read more

Winston's Cafe - This is a good price. - New American Near Me - Chesapeake, Virginia

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