"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."

"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."

"I was traveling for work and found this great cozy spot to eat! I like restaurants that are local to the area they're in. Winston's Cafe did not disappoint! I came in, sat down, I was greeted promptly, I already checked out the menu online and I ordered right away. The french dip sandwich was fantastic, and I am always looking for a good French dip. It was also trivia night and I was seated a bit far, but the host came over and made sure I felt included which I thought was very nice touch! I will definitely go back the next time I'm in that area!"

"Woooooonderful dive bar we rolled up on just checking out the area. Our bartender was fantastic! They also have an open mic night. The food, drinks, and service all grade A!"

"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."