Drew P.
12/31/2025
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...
Winston's Cafe
$
Closed
(208)
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1412 Greenbrier Pkwy Ste 133
Chesapeake, VA 23320
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!!
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Reviews
4.0208 reviews
Megan L.
10/19/2025
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...
Jared H.
10/11/2025
I stopped by Winstons on a Wednesday night for a quick bite to eat. If you are looking for a family run nice little whole in the wall place that has great food, friendly staff, and cool décor hop...
Rhondi S.
1/1/2026
Came in on a Friday night, they had live music playing, very cool!. Menu is diverse from appetizers (onion rings, nachos, steak bites, crab spinach dip, quesadillas, chicken tenders) sandwiches...
Nicole H.
10/6/2025
I had a delicious burger at Winston's Cafe. I ordered a mushroom Swiss burger with onion rings . It was so good, burger was juicy and perfect. Toppings were super fresh. The sauces that came with...
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