Cancel

Open app

Search

Winston's Cafe

4.0 (215 reviews)
Closed • 11:00 am - 12:00 AM (Next day)

Order Winston's Cafe Takeout or Delivery

Winston's Cafe Photos

Business Info

WINSTON'S CAFE ATMOSPHERE

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

More like Winston's Cafe

Portfolio From The Business

Sponsored

Recommended Reviews - Winston's Cafe

Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
Yelp app icon
Browse more easily on the app
Review Feed Illustration

Reviews With Photos

David K.

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!

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.

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.

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.

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.

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.

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!

Sequoyah V.

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

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

See all

9 years ago

Business owner information

Photo of Yolinda H.

Yolinda H.

Helpful 0
Thanks 0
Love this 0
Oh no 1

13 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

12 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

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

Helpful 0
Thanks 0
Love this 0
Oh no 0

9 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

16 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

13 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

8 years ago

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

Helpful 0
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

11 years ago

Helpful 1
Thanks 0
Love this 0
Oh no 0

10 years ago

Helpful 0
Thanks 0
Love this 0
Oh no 0

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.… 

What time does happy hour start?

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

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.… 

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

Winston's Cafe - newamerican - Updated October 2026

Loading...
Loading...
Loading...