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Inside
This is an overall view of the dining area.  Photo taken October 27, 2025.
Prime rib sandwich
Sandwich
This is the Burgers Page of their Main Menu.  Photo taken October 27, 2025.
This is the storefront for the restaurant.  Photo taken October 27, 2025.
Baileys Irish Cream Cheesecake
Winston's Cafe American Restaurant ·$$

Since 1990 Winston's Café has supported local, original and regional music acts. 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. 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..

Phone: (757) 420-1751

Cross Streets: Near the intersection of Greenbrier Pkwy and Crossways Shopping Ctr

Open now

  • Tue 11:00 AM - 10:00 PM

1412 Greenbrier Pkwy, Ste 133 Chesapeake, VA 23320 ·196.67 mi

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Amenities

  • Wifi
  • Smoke-free
  • Family friendly
  • Accessible

Reviews

yelp
4.0 217 reviews
5 star
103 4 star
55 3 star
27 2 star
14 1 star
18
Michael L. 10/28/26

Excellent chili, excellent quesadillas and good beer and wine selection. Beefy was our server. Beefy was outstanding. Will be back!!!

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Larry B. 10/19/26

Have been looking forward to trying Winston's Cafe for a long time. wanted to go during last week's restaurant week, but couldn't make it. Wife ordered the Rubin sandwich with onion rings. she...

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Ashley H. 05/03/26

Service was excellent. Very attentive waitress. Small family friendly bar/ restaurant. My kids had the chicken fingers and the grilled cheese. My daughter really enjoyed her grilled cheese. The...

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Drew P. 12/31/25

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...

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Rhondi S. 01/01/26

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...

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