Holy Cannoli!
Trust you me you don’t want to miss a slice of our Cannoli Cheesecake this weekend!

Hello Gorgeous!
Swing by this Friday and try our Crab stuffed Shrimp 🍤 🦀 they’re amazing!

Happy Cinco De Mayo!
Stop by and try one of our Delicious specials!
We have Margaritas, Coronas, Tacos, Quesadillas, and Burritos all on special 🌮😋😋😋

Sound Check Bingo tonight! 🎶
Join us for a night of fun 🤩 and you might even win something!

Today’s drink of the day:
☀️🐣 The Spring Fling: Rum, Peach, Pineapple, And OJ. 🍍 🍊 ☀️ 🐣

It’s Prime Rib night!
Starting at 5, stop by for a hunk of prime rib served with a salad and side for $18!
And don’t forget to stick around for Soundcheck Bingo! 🎶 🎵

We’re NUTS for coconut! 🥥
Stop by tonight and grab a piece of Toasted Coconut Cream Cheesecake!
(It won’t last long yall! )

Our German Chocolate cheesecake is calling ☎️ your name 😊
Stop by and grab a slice today, it won’t last long!


a month ago
This was my first time here and I had such a pleasant experience here. Crab dip was VERY good. The homemade potato salad stole the show - literally the best I’ve ever tasted. And then the cobbler was superb. There is nothing this place can improve on they are doing it perfectly. Thank you.
- Happy P
a month ago
Had a fantastic lunch! Ordered the Ahi tuna wrap. The tuna was cooked perfectly and tasted amazing. I let my three year old daughter try it and spent the rest of lunch defending my wrap from her. I was only able to accomplish this because her chicken tenders were equally delectable. We finished lunch with one of their homemade desserts. It was a delicate chocolate strawberry cheesecake that was the best I've had in years. We will definitely be back!
- Nicholas F
3 weeks ago
HANDS DOWN THE BEST PHILLY STEAK EVER!!!! I could not put it down. To die for! Definitely highly recommended. I am am out of town et but will be back every time I am here on business. My brother got the French Dip and said the same about his choice- the best!! You Must Go!!! Highly recommended.
- Ross C

A locals favorite since 1990

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 Winstons Cafe 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!! 

Contact Us


Call now
  • (757) 420-1751


Get directions
1412 Greenbrier Parkway #133
Chesapeake, VA 23320
United States

Business Hours

Mon:11:00 AM – 10:00 PM
Tue:11:00 AM – 10:00 PM
Wed:11:00 AM – 10:00 PM
Thu:11:00 AM – 10:00 PM
Fri:11:00 AM – 10:00 PM
Sat:11:00 AM – 10:00 PM
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