Winston's Cafe

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.

Love!!

Atmosphere: 5

Food: 5

Service: 5

This little place is great

Atmosphere: 5

Food: 5

Service: 5

Excellent food from a local gem, don't let the small size fool you, it is tucked into a spot next to a chain restaurant, but this place has a huge menu, and everything is done well. Speaking with locals they all had a different favorite and the staff knew them all. Leah was my server and she was amazing, I will definitely be back here every time I'm in the area.

We had a concert rained out and stopped in for a late dinner. Service was friendly and fast, food was hot and fresh and delicious. We had the lumpia, inside out burger and fries, and chicken parm. Definitely worth stopping by!

Atmosphere: 5

Food: 5

Service: 5

Recommended dishes: Fries, Burger

Thank u Leah for helping us out last night 😊
the food is great.

Atmosphere: 5

Food: 4

Service: 5

They had live entertainment which we enjoyed but table service was slow. I ordered an egg/cheeseburger that came with no cheese. Ahi tuna was delicious and so were the wings.

Atmosphere: 4

Food: 3

Service: 3

Friendly people and good service. I will be back to eat here again.

Atmosphere: 5

Food: 5

Service: 5

Winston's. What can one day to encapsulate the wonder and splendor of Chesapeake's finest little mom and pop. I've enjoyed their atmosphere and food for decades now and still continue to return back for more. The ladies are amazing. The live music is excellent. Simply said, I love this place. Never change Winston's.

Never change.

Atmosphere: 5

Food: 5

Service: 5

We stopped in for lunch. This is a local bar that opened up back in 1990. It's been quite awhile since i've last visited. The food here is hearty and homestyle. The French dip and the Winston Wonder were well prepared and tasty. It's a very narrow restaurant, limited seating with a small full bar. My only complaint is the tables are sticky, they need to be refinished. Everyone here was friendly,welcoming, and attentive.

Atmosphere: 5

Food: 5

Service: 5

Love this place. Hadn’t been here in a minute. But it hasn’t changed one bit. Stephanie is the bomb bartender b

Atmosphere: 5

Food: 5

Service: 5

We love Winston’s Cafe! My daughters and I eat here often. We can always count on friendly faces and good service.

Atmosphere: 5

Food: 5

Service: 5

Food was great , service was outstanding, thank you Leah!! and the atmosphere was awesome..
Will definitely be back..

Atmosphere: 5

Food: 5

Service: 5

Club Sandwich and Cranberry & Walnut Chicken Salad (Brioche) was out of this world! The potato salad is a SOLID choice.

Atmosphere: 5

Food: 5

Service: 5

Great flavor on their steak bites!

Atmosphere: 5

Food: 5

Service: 5