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    Winston's Cafe

    4.0 (214 reviews)
    Open 11:00 am - 12:00 AM (Next day)
    Updated 1 month ago

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    WINSTON'S CAFE ATMOSPHERE

    What's the vibe?
    Live music
    Moderate noise
    Casual
    Happy hour specials

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    Recommended Reviews - Winston's Cafe

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    Menu
    Rhondi S.

    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.

    Mushroom Swiss burger
    Nicole H.

    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.

    Menu
    Nicole V.

    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.

    Entrance
    Kerry B.

    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.

    Seared Tuna. Rare.
    Tracy T. S.

    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.

    Rueben pic #1
    Kristina H.

    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.

    Eggplant Parm (off menu special)
    Brad B.

    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...

    a plate of meat and a bowl of sauce
    Chrystal G.

    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!

    Really good food :) met the owner and her was really nice also! The crab and spinach dip was a rocket
    tone f.

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

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    13 years ago

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    11 years ago

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    10 years ago

    We went in for a late lunch. Sandwiches were excellent! I had chicken bacon ranch on brioche.

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    16 years ago

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    8 years ago

    excellent prime rib and onion rings and our waiter and the chef were attentive and animated!

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    Page 6 of 6

    Ask the Community - Winston's Cafe

    Is there still karaoke going on here?

    Hi Becca, not yet! We do have live acoustic on Thursday night and Music Bingo on Wednesdays. We would love to bring Karaoke back as soon as it’s safe.… Read more

    What time does happy hour start?

    Hi Maria! We have Happy Hour everyday of the week! M-F 3-7pm… Read more

    When do they have the live music and/or karaoke?

    Hi! We have Open Mic every Tuesday at 7pm, Karaoke on Thursday’s at 8 and live music, most Friday’s, some Saturdays. This Friday May 10, we have Dave Johnson at 8pm.… Read more

    View All 5 Questions

    Review Highlights - Winston's Cafe

    I had the "Winston burger", (beef,crab, bacon, and provolone) and mum had the blackberry bbq chicken tacos.

    Mentioned in 5 reviews

    Read more highlights

    Neat Bird

    Neat Bird

    4.1
    (263 reviews)
    0.7 mi
    $$

    Love, LOVE, LOVE!!!! @neatbirdva is always bringing the noise AND the funk, with their delish nugs…read moreand cocktails, and the quirky ambiance, with a side of Bob Ross * Sand shark, one of my fave cocktails * Nuggs, with their magic *fairy dust* (with miso ginger, of course!) * Bob Ross, on the TV They're banging out the old fashioneds at the bar, and have a great happy hour! This is a MUST in Chesapeake!

    This has become our new regular. We have been coming almost weekly since my last review and I…read morewanted to update. Old fashioneds are still great! They are my husband's go to drink. I usually get a martini, also great! and add in Gluten Free offerings and I'm sold! The wait staff are always so friendly and helpful. They have lunch specials which I have tried a few and have never been disappointed. I don't have a go to but the last time we went I enjoyed the Spanish chicken & rice and it was amazing. You get a decent serving so it usually ends up being a few meals for me. My husband got the crispy chicken sandwich with pickles on the side. He may not like them but I do! They are some of the best :D And we always get some of the homemade honey mustard sauce on the side for their fries. We have never been disappointed and I have not had an issue with their gluten free offerings. This is one of our faves and we will continue to come back over and over :)

    Photos
    Neat Bird
    Lunch chicken pot pie.  My wife and 18 yo daughter shared it and it was perfect.
    Lunch chicken pot pie. My wife and 18 yo daughter shared it and it was perfect.
    Devilled Eggs!  Soooo good.  Add the chicken seasoning for some spice.

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    Devilled Eggs! Soooo good. Add the chicken seasoning for some spice.
    The Spot

    The Spot

    4.0
    (23 reviews)
    4.9 mi

    Extremely disappointed, First time and last time trying this restaurant…read more We arrived at 1:17 PM and placed a to-go order. We were not given an estimated wait time. It is now 2:45PM over an hour later and we are still waiting with no updates from staff. I completely understand that lunch rushes happen, but communication is basic customer service. If the kitchen is running this far behind, customers deserve to be told upfront so they can make an informed decision. I was waiting in the car with my toddler, who fell asleep around 1:30 PM while we were still waiting. Sitting in a parking lot for over an hour with no communication is unacceptable. If you value your time, I would not recommend ordering to-go from here. Respect for customers' time clearly isn't a priority. Updated Finally received our food at 3:45 to only be left more disappointed by the portion sizes. Only received one piece of fish for a dinner, yams are not homemade and Mac and cheese was dry. They offered a free drink at 2:40 pm which doesn't nearly compensate for time. They continued to take orders by phone and in person and couldn't handle demand. At a point when your kitchen is over 2 hours behind, you need to push out the orders you already have and turn people away. I would much rather have been turned away and to try them on a different day with a coupon.

    Yum! We stumbled…read moreupon this place today and our whole family are huge fans! It took longer than expected to get our food but it all came out piping hot and super fresh! It was definitely worth the wait. I did not get enough pics but I'll add more next time. 2 of my kids had the burger and fries and they were great! Super soft and yummy buns! They were able to accommodate my sone and his allergies pretty well. He had the grilled chicken sandwich wrapped in lettuce with fries. It was well seasoned, hot and fresh! I got the fish and shrimp dinner and oh my! I won't be going anywhere else for fried fish! SSSOOOOOO GOOD! Not even a little greasy. So hot and fresh!

    Photos
    Porkchop with yams and corn on the cob
    Porkchop with yams and corn on the cob
    Fried fish and shrimp with mac n cheese and potato salad
    Fried fish and shrimp with mac n cheese and potato salad
    Porkchop meal

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    Porkchop meal
    Bubba's 33

    Bubba's 33

    3.8
    (385 reviews)
    1.5 mi
    $$

    For a chain restaurant, I am very impressed…read more First off, service was excellent. Our waitress was super friendly and quick. Food came in less than 15 minutes and drinks came in about 5 minutes. The place was packed so that was impressive Food was very good. I got the sunshine burger and my husband got the Cajun wings. The burger was very juicy and delicious. My only complaint was that the fried egg was cooked well done so the yolk was not runny. My husband enjoyed his wings. Drinks were delicious but a little light on the liquor. For $6 a cocktail I didn't expect heavy pours. Vibes were typical of a sports bar. It was a little loud but you could still have a conversation

    My family and I went to Bubbas 33 for an early dinner. They were busy, but it wasn't a wait for a…read moretable. They put us at a tiny table at first, but we requested something larger. The waitress was very nice about accommodating our request. They put us at a way larger booth which was more comfortable! It was a little louder because it was in the bar area, but it wasn't a problem. The inside where the bar is has several large screen tvs. There were several staff members there, and they were friendly. The menu has a good amount of options to choose from. Ranging from burgers, fish, steaks, chicken, apps, pasta, desserts, and etc. We ordered the shotgun shrimp, big o's onion rings, a mango frozen drink, blues lemonade, coffee, fish and chips, side salads, steaks, and Mac n cheese with chicken pasta. The food came out in a decent time. The only problem was my chicken and bacon macaroni came out after everyone had finished eating. It took 40 minutes for some reason, and they forgot the bread that comes on the side. It also had very little chicken in it!! The fish and chips were good. You get 2 good sized tempura battered fish. They weren't seasoned really, but tasted good with the sauce. The onion rings were tasty! They were big and definitely shareable!! They use tempura batter on them also. The sauce is like a smoky bbq sauce that went well with them. My parents enjoyed their steak and sides, they said the potatoes were good. My sister enjoyed her meal also. The side salad was a good portion. I enjoyed the shotgun shrimp. They were supposed to put the sauce on the side, so we sent them back and they corrected it with no problem. Our waitress Kaylee was very attentive, friendly, and upbeat! She made the visit enjoyable. I did appreciate that mostly everything was good! I wish I had gotten my bread and my Mac pasta was seasoned with more chicken. But I didn't check that until I got home since it was boxed up before we left. The front house manager Michael introduced himself and was very friendly as well. It was our first time there and he gave us a warm welcome. I'd definitely return to eat here again! Check them out!!

    Photos
    Main dining room.  You can see ANY sports you desire
    Main dining room. You can see ANY sports you desire
    Hot and Spicy chicken sandwich with seasoned fries
    Hot and Spicy chicken sandwich with seasoned fries
    Watermelon Margarita

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    Watermelon Margarita

    Winston's Cafe - newamerican - Updated June 2026

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