Winston's Cafe

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.

The best food and the best people in Chesapeake. Absolute staple, love you Winston's ❤️

Atmosphere: 5

Food: 5

Service: 5

Beef he is a good bartender and the cooks definitely cook the best tuna bites in Greenbrier A+ from Kenney’s Restaurant Equipment

Atmosphere: 5

Food: 5

Service: 5

WINSTONS IS THR BEST PLACE ON THIS SIDE OF GREENBRIER. Don't pass it up.

Atmosphere: 5

Food: 5

Service: 5

We stopped by today for the famous reuben sandwich. It was delicious and the coleslaw was a pleasant surprise. It was some of the best I've had. We even ordered a second bowl. We will definitely be back. Mike was a great server.

Atmosphere: 5

Food: 5

Service: 5

It's not there anymore!

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.

This is a gem we were happy to have been referred to by the motel staff! We were welcomed, seated and made to feel welcome. The food was exceptionally good! BEST shrimp dinner I’ve had in ages (and we’re from Seattle…the seafood capital of the NW). The ribs were done excellently and the potato salad was made in house!! Think we’ll go back for dessert for lunch tomorrow!!! Beefy P was a great host!!

Food was great, service was great, atmosphere was a little loud but tolerable. Highly recommended 👌

Atmosphere: 4

Food: 5

Service: 5

This hidden gem is one of my favorites in Hampton Roads. The service is phenomenal the food is delicious and the atmosphere is cozy. I’ve never had a bad visit. The catfish melts in your mouth, the spaghetti (chicken parm) is some of the best in the area

Atmosphere: 5

Food: 5

Service: 5

Wonderful. Good food

Food quality and service are excellent! It is small on the inside and can be a little noisy at times but you really can't go wrong with Winston's, in my opinion. Thank you

Atmosphere: 5

Food: 5

Service: 5

Menu emphasizes fresh seafood and Southern-inspired flavors

This was the best service in the hampton rods area!! The food had great flavor- the best philly cheese in years. A bonus was the music jammin in da background.

Atmosphere: 5

Food: 5

Service: 5

Recommended dishes: French Dip Sandwich, Winston’S Jumbo Wings, Wings

Love!!

Atmosphere: 5

Food: 5

Service: 5