What a fortuitous find! My wife and I discovered this gem by accident as we finished some shopping in Chesapeake. I ordered the Texas Burger with fries and my wife ordered the Mushroom Swiss Burger. Both orders were delivered with efficient speed and both the fries and the burgers were piping hot upon arrival! My Texas Burger was absolutely delicious and I went through that thing like a hot knife through butter! My wife and I both agreed we had not had burgers this good in quite some time! The services was excellent! We will definitely be back to Winston's Café! read more

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Winston's Cafe is located in the Crossways Shopping Center in Chesapeake. It is near the intersection with Greenbrier Pkwy and Eden Way N. It's in the same group of buildings such as Michael's (around the corner). My visit here was on October 27, 2025. The outside view of the business is simple, but effective. They have a specials chalkboard next to the entrance. Parking wasn't an issue on this visit, but I'm sure it can fill up at busier times. My mom and I were both in the area as she wanted to go to the Michael's store here. When we came inside, it wasn't busy, as it was around 3:30 pm when we got here. We were greeted by the one who would be our server for this visit. He gave us menus to look at and asked us for our drink orders. I generally stick with water with lemon, which I did here. We were there during the time where it was still the lunch menu (though for us, it was more like dinner for us that day). When he came back with the drinks, he asked if we were ready to order, but we weren't just yet. He also asked if we had any questions about the menu and options and gave us more time to mull over the menu. When he came back, we weren't completely ready, but asked a question about the specials of the day. After that, we knew what we would get and placed our food order. My mom ordered the Meatloaf Lunch Special with mashed potatoes and spinach. I went with the Meatball Sub Lunch Special with mashed potatoes, though I don't normally do potatoes that often. After about ten minutes or so, the food came to the table. The food looked really good, and it was hot too. The bread for the Meatball Sub was very soft and easy to eat. The meatballs were huge and made for a worthy meal. The mashed potatoes with gravy was really good and fulfilling too. My mom loved the meatloaf, and their meatloaf doesn't have ketchup on it like some other places do. She loved the meatloaf, spinach, and mashed potatoes too. After we were done, he asked if we wanted any desserts. We both declined as I normally don't do them anymore. Overall, we both had an excellent experience here. The food and service were on point. The food I had that day did spike my blood sugars, but I expected that with bread and mashed potatoes. I don't make a habit of that though. They are a great local business. There are lots of food options to choose from. If you are looking for a place to eat while in this part of Chesapeake, this place is worth coming to. read more

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Service was excellent. Very attentive waitress. Small family friendly bar/ restaurant. My kids had the chicken fingers and the grilled cheese. My daughter really enjoyed her grilled cheese. The chicken fingers were more of the bread crumb breading compared to batter so it came off as she tried to break the chicken in half. I had the French dip. It was very good. My husband had the buffalo chicken wrap. He enjoyed it as well. We got the mozzarella sticks as appetizers and they were good. Not sure if they were worth the price but my daughter enjoyed them. I was a little disappointed because the pictures all showed beer battered fries and they came with crinkle fries. If we would have known that we wouldn't have paid for the up charge to get fries. read more

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

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Came in on a Friday night, they had live music playing, very cool!. Menu is diverse from appetizers (onion rings, nachos, steak bites, crab spinach dip, quesadillas, chicken tenders) sandwiches (Philly cheesesteaks, club, chicken Parmesan, wraps), entrees (ribs, chicken Parmesan), soups, and salads. We had the chicken Philly sandwich, French onion soup and salad. All of the food was fresh and delicious with a great server who is very helpful, courteous and friendly. Great tasting food, fun ambience. read more

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I had a delicious burger at Winston's Cafe. I ordered a mushroom Swiss burger with onion rings . It was so good, burger was juicy and perfect. Toppings were super fresh. The sauces that came with the meal were amazing. Our server was attentive and nice. It was a surprise to come to a game night. Wednesdays they have music bingo. It was a lot of fun ! And the crowd was great! There was a couple that won a free dessert. Plenty of parking, location is across Greenbrier Mall . It is a cool spot to eat. read more

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

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I stopped by Winstons on a Wednesday night for a quick bite to eat. If you are looking for a family run nice little whole in the wall place that has great food, friendly staff, and cool décor hop on over to Winstons. Winstons has some great sandwiches / burgers, I ordered the Winston burger. It comes with a generous beef patty, lump crab meat, sauce, L/T/O, and cheese, DELISH! Another awesome thing is you can get onion rings as a side. Winstons also has a small bar to get your favorite cold beverage to wash down your meal and enjoy the atmosphere. I went on a Wednesday night and as a surprise Winstons hosts music BINGO on Wednesdays from 6-8. Winstons is located in a strip mall with several other businesses so there is ample parking. Winstons is a fantastic spot, can't wait till the next time I go back. read more

We were greeted by our server Stephanie who was just wonderful! We had a delicious appetizer of Lumpia. Our French Dip and Pastrami Rueben were so good! We will definitely be back. read more

I'm not sure why this place has good reviews. We waited a while for our food. I watched it sit at the window ready. When it got to our table it was barely warm. The au jus for my dip was cold. I asked for it to be warmed up twice. The first time they tried to microwave it for 30 seconds and that still wasn't hot. Then they put it in for 2.5min and it was hot. (I could see the microwave) It was a sad waste of money. Service was slow and uninviting. It seems everything is just reheated and it tasted that way too. It was overpriced for reheated/room temp food. read more

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Nice casual restaurant with good service. The burger and fries were fresh and well cooked.Music made the evening even better.

Winston's is a solid pub/ restaurant in Chesapeake. It has been in the same location right next to Ruby Tuesday's for over 30 years, so they have to be doing something right. I have been here about three times so far, and the service has been stellar. From my first visit I felt welcome and when I am in the area, I plan to be a regular. Mike and Codie were my servers. Codie is a gal and if full of personality in a good way. My favorite item so far is the mother of all meatballs. It was so good I wanted to lick the plate. It was hitting just right for me. They have a full bar and craft beer on tap. There are TVs and a juke box. I am told that when the weather gets cooler they will start having live music again. read more

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I got food poisoning from there, worse 24 hours. Service was great, tea was good. Stay away from the meatloaf

I do enjoy and recommend Winston's, but would like to also give a shout out to our waitress and cook working 10/18/25 around 11:30, and also a concern to one gentleman who showed up for work around then as well. I wish I had names, especially for the amazing waitress who served us (she was blond, I know that!). I came in with my daughter and elderly father who has dementia. Dad wanted an egg sandwich. We had already driven by some of the usual breakfast spots and naturally they were packed. I stopped because I had seen that sometimes Winston's offers brunch, and learned that at least yesterday they did not. However the waitress checked with the kitchen, they had eggs, bread, and bacon and the cook graciously agreed to make my dad a sandwich. So very kind of them and very much appreciated!! ABOVE AND BEYOND!! My daughter and I ordered regular menu items and while waiting for our meals a gentleman came in carrying some groceries. I guess he saw the cook making an egg sandwich when he entered the kitchen and proceeded to loudly berate both the waitress and cook, yelling about how, "We don't f@ck!ng do breakfast, we don't make eggs, it's not on the menu, you have no right to make that f-ing guy eggs, all to what? Keep one f-ing customer?" I am paraphrasing, but not exaggerating at all - he was cursing them out, f-bombs and all, and it was quite easy to hear from where we sat, as the customers in question. I felt awful to have gotten the waitress in trouble, and hearing him treat staff this way as well as talking about paying customers this way put a bad taste in my mouth during what would and should have been an outstanding experience. So, a huge thank you to 2/3 of the staff I encountered yesterday. Food was great, service was great, but that one guy really needs to find some zen - and he could learn a thing or two from the rest of the staff regarding customer service. read more

The service/ waitress very friendly and food was great. nice atmosphere. Service was quick. Had some nice specials and a band. read more

Love this local spot for me. I'm about 5 minutes away. I'd been before, but it was during the day. Great place then, not really anything special. This visit however, maybe because I was craving a great burger (theirs is 1/2 pound!) I stopped in. Glad I did. Had a cheese burger, with all the accoutrements; lettuce, tomato, onions, cooked medium rare. I could tell by the meat juices on the plate, that it was cooked perfectly, before I bit into it. I was right. Delicious. I had it with their homemade coleslaw. Excellent!! For an appetizer, I had the seared Tuna bites, cooked rare. This too, was perfect. Their sweet tea and lemonade is also very good. Host/server was very hospitable and accommodating. Not overbearing, but attentive. Even the chef was hospitable, asking if the temperature was correct. "Yes Chef, it was." Decor is basic. Nothing outstanding. Nothing exceptional. I'll definitely be back. read more

Winston's Cafe - Seared Tuna. Rare. - New American Near Me - Chesapeake, Virginia

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It's Friday night and we wanted something different. I was looking for ideas on Yelp and this place popped up. I then went on Facebook and they have a specials board that they change daily for lunch and dinner, that impressed me that they consistently update. It is a very small "hallway " type restaurant, you seat yourself. We were lucky there were 2 tables available. In addition to the outdoor board specials they also have chalkboard specials. I decided to start with the special soup, polish sausage and potato. It had great flavor and was perfect on this cold night. My husband got hot wings and they came out naked, brought out by another staff member not our server. Our server came and checked on us and noticed they were not quite right and took them back to the kitchen to have them sauced. My husband loved that they were fall off the bone tender with a crispy outer crust. My husband judges restaurants by their Rubens, so that's what he got and he honestly thought they made it in house. It was so tender and had a nice char on the meat. I chose one of the outdoor board specials of the night which was a Greek chicken stuffed with feta and had a spinach, blistered cherry tomato sauce with rice and balsamic vinegar. It was absolutely delicious, the flavors paired really well together. We both had enough to take home for lunch for the next day. Our server was super nice and it seemed like she was the only one working so she was busy but still attentive. We want to go back and try some of their other specials and they make homemade desserts as well. I think you will be pleasantly surprised if you go and give this place a try. Let me know what you think. read more

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Winston's was fine. I had the chicken sandwich and it was delicious. However, everything else we had was just ok. Nothing stellar and nothing we will return for. We also had wings, ribs, and mozzarella sticks. They had decent happy hour specials (until 6) and our server was friendly, however there were some small issues with food coming out like it should (our mozzarella sticks were sent to the wrong table so we didn't get them until after we had our meal). The ambiance was very casual and nothing impressive, though that doesn't matter much for me. It wasn't a bad meal or experience, but not a place we'll go back to. read more

This place is a solid "meh" for me. While my son raved about the crabcake burger, it's pretty hard to screw that up. I had the off-menu special eggplant parmigiana. Having spent 5 years living Italy, I jump at opportunities to jump on a menu item such as this, to bring me back to Italy. I was dead wrong, very salty, couldn't even taste the eggplant, the cheeses were over powering and not very high quality. Sadly, it was a disappointment for me. Nonetheless, the service was pleasant and checked in frequently. With that, it puts them at a solid 3+ stars in my book. Winston's is worth a look, perhaps stick to the on-menu items if you try it. The place just seems like more of a pub/sports/dive bar than a restaurant or cafe. Not my scene usually... read more

Winston's Cafe - Eggplant Parm (off menu special) - New American Near Me - Chesapeake, Virginia

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This is my go to spot in Chesapeake. Every time I come to Virginia the food is amazing, the service is really good and the bloody Mary's are exceptional. The live entertainment is pretty good too. read more

We go there often but this time the food seemed off. Ribs weren't tender like usual, my go -to sandwich had an unusual taste, skimpy amount of fries with our entrees. Our service was great, drinks were fine but a disappointing evening read more

I hate to rate this place a four, I really do. But this place hasn't changed in all these years. I worked here many moons ago. Pretty sure I saw a few familiar faces for the short amount of time I spent in there. The atmosphere is drab really. Dingy almost. Doesn't stop it from being a cool place to hang out sometimes. If it's your scene or your local watering hole. The food is hit or miss. Always has been. This time the steak bites were okay the wings were dry, the spring rolls weren't great, but the nachos were awful. And they're so hard to mess up. I'm sure I'll be back. I always get around to it every few years. But it'll be a while. I did want to add that our server was great! Can't bash the employees there! They're always top notch! read more

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Really tasty especially the crab dip and Winston burger ! Owner was also nice he crack on us before leaving read more

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This little gem has been hiding in my area and I never knew! The food is so good, the staff were so nice. Hubby had the ribs and I got the surf and turf. They have some great specials read more

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

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Fantastic. The lumpia appetizer was perfectly fried with tasty chili sauce. We got the crab and seafood Alfredo and the Friday surf and turf special, 2 beers, and a tea. The total was $78 before tip. Surf and turf was 8 very fresh shrimp and an 8 Oz ribeye, with mash potatoes and sautéed green beans. The pasta was a huge portion with crab and plenty of shrimp in each bite with a large hunk of garlic bread. Things were fresh, large portions, well seasoned. Our server Jenny was very attentive, and Mikey too. Don't let the dive atmosphere throw you off. We came over from across the tunnel from Newport News to do some holiday shopping nearby, and we are always looking for delicious local spots to check out. We will be back! read more

I have dined here twice now and it's safe to say I love it here! I ride by here all the time. I mean it's maybe been in existence for maybe five years, and I ride by and say, I wonder what that place is like? ____________ Well I just found out (as of 2021) - Frankie the manager at Winston's Café wanted to let me know they have been open 30 years! _________________ Well this past year, my babe and I dined twice, sat near the bar and the bartender took care of us both times. The cocktails were on point. The food delish! The atmosphere was giving me very much, Cheers vibes! You know the back in the day TV show. This place seemed to have a lot of locals or friends of friends. On both visits, the vibes were super high and I can recall some folks I saw on my first visit on the second visit. This seems like a super chill and friendly place to grab something to eat, watch TV and just chat it up with folks around you. I highly recommend you check this place out. We visited both times on Friday evenings. Parking, no issue. It is located among other eateries and shopping. Have fun and enjoy life :) read more

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Winstons is one of our favorite spots in greenbrier. We went next door to check out ruby Tuesday but after waiting to be seated for almost 7 minutes in an empty restaurant we walked next door to Winstons, were greeted immediately with a friendly smile. I ordered the French dip and it's one of the best I've ever had, it came Out quick and hot and there was a guitarist playing. Highly recommend this restaurant if you are looking for food in the greenbrier area. read more

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

We stumbled upon this hidden gem of Chesapeake when other restaurants were closed and my toddler would only settle for chicken tenders! I love the ambience of the cafe, it's more roomy than it looks on the outside and it was spread out! The service was fast, wonderful, and efficient! My daughter got the chicken tenders and fries which were really good (I snagged a few fries)! I got the namesake burger which was alright, but nothing will ever compare to how fantastic the onion rings were. They were crispy and came with a sauce on the side that elevated them to the next level! read more

I've been to Winston's many times in the past but this is my first Yelp review for them. I look at the Specials on the board outside the door and I noticed that the offered She Crab Soup, one of my all time favorite dishes. I sat at the Bar and ordered a Vodka Soda. It was a generous pour and it made for a good drink. The Bartender was attentive and helpful with menu questions and suggestions. I started off with the aforementioned She Crab Soup for $6, just a Cup, as I intended to order other food items. The She Crab came out right away and it was presented in a less than average manner. I looked like they just slopped it into the cup to get it out as quick as possible. The Soup itself was less than average and certainly nothing that should be put on the Special Board. I've had soup out of a can with more flavor. I ordered the Burger with Pepper-Jack but I was told that they didn't have any Pepper-Jack. I politely asked for the check, paid the bill and left. This place has gone down hill since the former Chef, Jack stopped working there. read more

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i've literally never written a review on yelp before but omg. my girlfriend and i came here to end our date night. not only was our tab $53 for a tequila soda, a white claw, and four apps, but everything was SO good. our server's name was tara and the service was great, but sorry girl the star of the show was the crab and spinach dip. i'm not even being dramatic when i say i'll be having dreams about this dip. it was literally that good. the bread that it came with was good but we genuinely used whatever possible to eat as much of it as possible. the atmosphere was very chill and there happened to be live music which was also nice. such a good price for a chill, local place, will definitely be coming back :) read more

Perfect little spot!! The food, the ambiance and the service were all just awesome!! Live music by Chris Morrow, rocked the house! I started with the potato soup, now, when I say that this is the best potato soup that I have ever had, I am a veteran of hundred of bowls from dozens of place! The soup alone was worth going!! Following the soup I had the biggest and one of the tastiest club sandwiches that I have ever been served! And the fries were also top notch, crispy, not greasy at all, beautiful!! Ask about the desserts, we had the peach cobbler with ice cream, it was hot and with the cold ice cream just spectacular!!! Tara was super friendly and efficient, and saw to it that we had everything that we needed, so nice! You have to go here!! If you can go on a night when Chris is playing you'll thank me even more!! I will be back again and again. read more

Winston's Cafe - Great ambiance and lots of smiles!! - New American Near Me - Chesapeake, Virginia

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Friends from the neighborhood suggested this place after our first choice told us that there would be a 30-minute wait. Thank goodness for 30-minute waits. Winston's was a wonderful choice, and I highly recommend it for casual food. Our friends said they found it because it offered a Thursday prime rib special. We were there on a Saturday, so no prime rib, but the food was excellent and the bar was one of the friendliest places in which I have eaten in a very long time. as soon as we walked in, Leah led us to a table and waited very attentively on us in that friendly, fun manner you want. I ordered Maker's neat from the bar and the pour was significantly bigger than anything other than what I pour for myself at home. Everyone else in Winston's was clearly having a good time; it was a relaxed fun place. The servings were generous (like the bourbon). When the check came, I thought Leah had forgotten to include something; it was incredibly reasonable. Oh, and let me add another good word for Leah, who was just excellent. We're from Kentucky and won't get to eat at Winston's for another year or so, but if I lived in the Chesapeake area, Winston's would be a weekly stop. read more

Came here with my mom for a quick bite Food was good and so was the service. Would eat here again.

Post st Patrick's day visit. We had nachos, yummy Potato soup was great Seafood quesadillas was different but really good. Hubby had chicken parm sandwich and loved it. Service was paced well and server was friendly. Beer was cold food was hot.... Great find!! read more

A friend and I stopped in for lunch. The server remembered us. We had only been once before. That was impressive. We each received our food and enjoyed it very much. We also had a great conversation with our server and she educated us on a few food related topics. read more

This has been my go to great food spot for 10 plus years. The service is amazing, no matter the change in waitstaff they care about their customers and regulars. Don't let the bar vibe put you off, you won't be disappointed. read more

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

Great service great food! Waitresses was awesome. Great bloody Mary's . Reuben was great!

Winston's is a wonderful local pub "where everyone knows your name." Many of us meet a few days per week but there is always room for new friends. There are ~15~ tables where patrons enjoy items from a varied menu including man items ranging from my favorite French Dip to quesadillas to scallops to... And every member of Greg's staff will take care of you, so much so that your first visit will not be your last. Is this too much? Sorry, but this is my favorite place to visit. read more

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

Yep, just like I remembered! Tacos are amazing annnnd they won't disappoint you. They fill me up and have specials on Tuesdays! If you could go any other day during the week they do offer other specials great for dinner as well. read more

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

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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

When we moved to the area in August of last year we decided that Winstons would be our place to go when we didn't want to cook and didn't know what we wanted. The place has a great vibe and the servers couldn't be more helpful. Fast forward a few months and I think they must have cycled out the kitchen staff for sure because the last couple of visits have been pretty bad (I'm being polite). Today I had an issue with onion on the food (onion allergy and notified my waitress) the waitress was great, very apologetic and did her best to make things right. By the time the food came back the burger was tepid and my fries were cold and my appetite had left me. Not for the first time in recent visits I left Winstons as hungry as I arrived. It's sad to say this might have been the last visit (for food at least as I do love the musical bingo evening), I really want this to be my local go-to place but right now the god awful Ruby Tuesday's next door is looking more appealing. read more