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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?
    Casual
    Live music
    Moderate noise
    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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    9 months ago

    Business owner information

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    Greg E.

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    4 months ago

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

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    2 years ago

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    4 months ago

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

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    2 years ago

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

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    1 year ago

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

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    3 years ago

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    2 years ago

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

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    6 years ago

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    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

    McGrath's Burger Shack

    McGrath's Burger Shack

    3.9
    (159 reviews)
    5.4 mi
    $$

    It was 245 in the afternoon on a Tuesday and my son and I were the only customers in the…read moreestablishment which I thought was weird but as it seems more of a bar than a restaurant that makes sense. Our waitress was friendly and attentive. I loved the pretzels but I will say that personal my burger had too much bun. Good flavor but I think the bun was overwhelming compared to the actually burger. My son loved his burger which is not pictured but had a fried egg on it.

    First time trying McGraths while being in the area. After we ordered and received our drinks (tea…read moreand water), we were then told that the kitchen only had one worker and it was a long wait. Not sure why they couldn't tell us this before the order. Anyway, no biggie. We ordered an app, mozz sticks and split the 4 cheeseburger sliders with fries. The mozz Sticks came out about 40 min later. They were so over cooked that all the cheese was completely blown out of them. We tried a few and it was nothing but bread. The waitress was nice enough to take them back and just remove them from our tab (it would be too long to wait for them again). Another 20 minutes and we received our order. The fries looked amazing!!! I was so disappointed to find out that looks can be deceiving. They had no flavor. I feel like maybe it was an oversight? I have read other reviews and others raved over them so, maybe the kitchen just forgot to season them. But they tasted like pure oil. But those burgers. Holy moly. Those burgers are were soooooo good! They don't make up for the others but I was glad not to leave there hungry. They gave us a coupon for our next time coming in. Told us not to open it and let our waitress, so they could tell us what our percentage off was. I opened it in the car bc I will not he back. It was 10% off in case others got this as well. Just a heads up

    Photos
    McGrath's Burger Shack
    Irish Whiskey Burger
    Irish Whiskey Burger
    Irish Car Bomb

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    Irish Car Bomb
    Bubba's 33

    Bubba's 33

    3.8
    (384 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
    Jack Brown's Beer & Burger Joint - Norfolk

    Jack Brown's Beer & Burger Joint - Norfolk

    4.3
    (755 reviews)
    6.0 mi
    $$

    jack brown's was so so so so good. the place is super tiny and packed -- but not uncomfortable,…read more that's kinda what made it fun. the staff were really busy but still nice, and the whole vibe of the place was cool. i loved all the decorations around the bar, especially all the dollar bills with writing on them everywhere. it made the place feel really unique. the burgers were amazing and the sweet potato fries were literally some of the best i've had. definitely somewhere i'd go back to if i'm in the area again.

    My party came here on Sunday afternoon after visiting Nauticus with our kids. The burgers were good…read moreand fresh, but smaller than expected for a place known for burgers. Price point was about $16 for a burger and fries without a drink. We ordered the regular cheeseburger, the Cowboy (bacon, BBQ sauce, and American cheese), the Cobra Kai (cream cheese, pickled jalapeños, and jalapeño jelly), and the Classic Jack (caramelized onions, JB sauce, and dill pickles). Everything tasted solid and came out hot. The restaurant itself is very small and does not seem ideal for larger groups. Despite this, I loved the ambiance, it has a dive bar vibe with lots of notes on dollar bills on the walls that were fun to read. I will be coming back again when in the area! A special shoutout to the waitress with the bridge piercing. She was friendly, accommodating, and quick with service, which really stood out.

    Photos
    Interior
    Interior
    2x fried Oreos (interior view) (instagram: @issa.cheatday)
    2x fried Oreos (interior view) (instagram: @issa.cheatday)
    View from within the restaurant

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    View from within the restaurant
    Bubba's 33

    Bubba's 33

    3.7
    (100 reviews)
    10.6 mi
    $$

    We were hungry after the girls' volleyball game and decided on Bubba's 33. Neither one of us have…read morebeen there before. We arrived shortly after 7. The place was packed but we were seated right away. There is a full bar and over 30 tv's. This would be the perfect place to watch several sports at once. They have bar, table and booth seating. The bathrooms are small but clean. I liked being able to see into the kitchen as well. Our server, Ariana, was an absolute gem. She promptly took our drink orders and our appetizer request. We got the combo appetizer which had boneless wings, twirly mozzarella sticks and fried pickles. HIGHLY recommend. Although it did take a little longer to get it, everything was hot and cooked perfectly. Ariana did explain how everything is cooked fresh so we expected to have a bit of a wait. For our entrees, I ordered the Monte Cristo with fries and my boyfriend had the sunshine burger with loaded tater tots. These took a lot longer to come out. We watched several people come, eat and leave before we got our food. Ariana kept us updated and was very apologetic. The Monte Cristo was the perfect balance between sweet and savory. The burger was full of flavor and huge. The loaded tots, unfortunately, they did not come out that way. Our server tried to get the kitchen to make a fresh batch, but to be honest, we were just tired and ready to go at this point. We are very empathetic when it comes to a busy restaurant. Ariana was doing everything she could to try and get our food on time and kept checking with the kitchen. I'm honestly surprised that the supervisor did not come over to check in. Our bill even had a charge for the games on the kiosk, which we did not play. However, we were just ready to go home at that point. The food was delicious. Our service from our server could not have been better. Disappointed with the management , I feel they should have been more helpful to the staff and to the customers. Especially since the order was not completed fully and we opted to leave without the requested loaded side. The prices are great and the portions are generous . I would love to try more of the menu! We I'll probably go back, maybe just at a different location or not around dinner time. It was a pleasant experience. If it were not for our server, my review would be a bit more critical.

    First time last Sunday we went to Bubbas 33, and the waitress was phenomenal. She took our orders…read morecame back look like every 15 min to check on us. The establishment is a very very nice sports bar with the best food I have had in a long time. I'm going back really soon I had steak and mash potatoes which was great but a platter with fried fish went by and I was in love, so fried fish I'm coming back to get you soon. Keep up the great work, Blessings

    Photos
    Mug shots
    Mug shots
    Bubba's 33
    Bubba's 33

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    Winston's Cafe - newamerican - Updated June 2026

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