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Winston’s Cafe is one of the original local businesses in now booming Greenbrier. We serve fresh, quality, made to order food, along with our highlighted daily lunch and dinner specials. Since 1990 Winston’s Café has supported local, original and regional music acts. We also pride ourselves in a friendly atmosphere and are committed to providing excellent customer service. Come to Winston’s for your next casual dining experience!!
Welcoming, casual hangout featuring classic & creative American eats, live music & cocktails.
Address and Contact Information
Address: 1412 Greenbrier Pkwy #133, Chesapeake, VA 23320
Phone: (757) 420-1751
Website: https://winstonscafe.com/
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WINSTON’S CAFE | Chesapeake VA – Facebook
WINSTON’S CAFE, Chesapeake. 4020 likes · 290 talking about this · 8415 were here. Good food, good drinks, good people. A locals favorite since 1990!
Winston’s Cafe
• Chesapeake, VA 23320 (757) 420-1751. HOME · MENU · CATERING · GALLERY · ENTERTAINMENT · CONTACT US · Winston’s Cafe. Chesapeake. 1412 Greenbrier Parkway #133
Winston’s Cafe – Visit Chesapeake
Winston’s Cafe has been serving delicious, fresh meals in a fun and … 1412 Greenbrier Parkway, Suite 133, Chesapeake, VA 23320; Phone: (757) 420 …
Reviews
Drew Petzold
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.
… moreThe 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.
David Kane
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!
… moreI 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!
John Hannan
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.
… moreWillie Porche
Simply an amazing restaurant to eat at. The food, the atmosphere, and the service are all top-notch. From the delicious prime rib to the meaty club sandwich, the amazing Ruben. I honestly can’t wait to come back. The absolute only issue was I ate too much. I just couldn’t stop.
… moreRyan Riffle
My family has been coming here for years when they were under the previous ownership, but we came today because it’s a family favorite and this place never disappoints. They have a $.79 wing deal and it’s great and available everyday at happy hour from 3-7pm. Also their Mac and cheese is delicious! It’s always made to order, creamy, and fresh! Overall a great restaurant to visit with friends or family
… moreKaszia C.
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!
… moreFonzy F
Cozy hole in the wall
Had the flounder basket, it was delicious. My server was great, made me feel like a regular and I’m from out of town. Highly recommend. The breakfast beer was a better version of Guinness.
… moreHad the flounder basket, it was delicious. My server was great, made me feel like a regular and I’m from out of town. Highly recommend. The breakfast beer was a better version of Guinness.
Ray Albertson
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.
… moreMatea L.
2/6/23 – The food is delicious. I love their chicken salad the most. The French dip sandwich was good as well. Ever since I brought my mom to this place she loves it. The service was super quick and always the staff is so nice and friendly.
… moreMay Zaporteza
Portions were good for a light meal. The server was great and made sure we had what we needed. This place is ideal for small groups or dining alone. I like the cozy vibe!
I might try some of their homemade desserts next time!
… moreI might try some of their homemade desserts next time!