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. Based on 617 reviews, the restaurant has received a rating of 4.4 stars. Price $$
✔️ Dine-in ✔️ Curbside pickup ✔️ Delivery
Address:
1412 Greenbrier Pkwy #133, Chesapeake, VA 23320
Phone: (757) 420-1751
Social Profile: 
Hours
| Wednesday | 11 AM–12 AM |
| Thursday | 11 AM–12 AM |
| Friday | 11 AM–12 AM |
| Saturday | 11 AM–12 AM |
| Sunday | 11 AM–8 PM |
| Monday | 11 AM–10 PM |
| Tuesday | 11 AM–10 PM |
Menu
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Menu Photos
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Reviews
May 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!
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Muhhtayyuhh_09
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.
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Robert Brown
I had the pleasure of eating at Winston’s Cafe tonight. I really really enjoyed eating there a lot. First of all the menu had a lot of dishes that looked really good to me. I had a difficult time deciding what I wanted to get because there were so many things that looked good. I got the chicken parmesan and was so happy I did. The chicken was cooked perfectly and was on a generous bed of pasta. The sauce was really delicious too. It came with a nice size piece of garlic bread. The portion size was generous. I love going out to eat and getting a truly wonderful meal, and the menu items were all very reasonably priced. The staff were pleasant and attentive with keeping my drink refilled and making sure I had everything I needed. If you haven’t dined at Winston’s I highly recommend you give them a try. You will have a wonderful meal and support a local business at the same time. What could be better than that?!!!
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N P
Great atmosphere, drinks and food. French Onion soup was very good.
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Jim Mershon
My wife and I went here after being in the neighborhood for something else. The food was delicious. The Rueben was some of the best I have had in a while – not the excessive half-pound of meet and quarter cup of dressing that you get at many other places, but the whole sandwich was full of flavor, with high quality pastrami, I think heated on the flattop. And we could tell why the french dip was “famous”. And the service was personable and just the right amount of attentiveness. Will definitely come back the next time we are in the area.
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Ryan 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
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Joshua Sheffield
Great food, great atmosphere amazing food. Nice little local spot. Wish we had visited sooner, might be our new go to place. Had onion rings, French dip and both were really excellent.
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donald mittelstaedt
What a fun place! Great food and terrific atmosphere with lots of people having fun and enjoying themselves. Don’t be deceived by the outward hole-in-the-wall external appearance – good food and good times inside.
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Elizabeth White
This place cleaned up really nice. I hadn’t been here in a long while, so I thought I would bring my sister here. While her and I were chatting, I waved to someone I thought was waving to me. He started yelling at me that I shouldn’t be saying hi to men who are with their wives and girlfriends.(he was a rather over size man, not my type) Apparently, he used to own the place and thinks he still does. I will think twice before I bring anyone there again.
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Frank Mayhorn
We read the great reviews and planned on eating here. When we arrived there were 3 people outside the entrance door smoking and that turned us off on the place (unfortunately). Management needs to be conscious of how this appears to the public. Have your employees or customers smoke out back or away from the front.
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