Winston's Cafe

Winston's Cafe

1412 Greenbrier Pkwy #133, Chesapeake, VA

★★★★★4.4(748 Google reviews)

Crema's Take

“Winston's Cafe is a beloved neighborhood institution that's been perfecting the art of comfort food since 1990, with standout sandwiches like their legendary French dip that reviewers swear are the best they've ever had. The cozy, homestyle atmosphere makes it the perfect spot to linger over a meal, whether you're a local regular or stumbling upon this gem by accident while shopping in Chesapeake. It's the kind of place where attentive service and hearty, well-executed food combine to create an unexpectedly special dining experience.”

What to expect

Classic coffee drinks done right. A slow-sit spot, good for meetings. Full breakfast and light food on the menu. Parking available.

MeetingsSlow sitLight foodParkingFull breakfastTraditional drinks

Google Reviews

JF
★★★★★2 months ago

I saw another review on here that said their wife had the French dip and said it was the best they’d ever had in their lives. I agree. I got this as deliver and sandwich was fantastic even being cold when it got here. By far the best French dip I’ve had in the 757 and will be…

David Kane
★★★★★2 months ago

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…

Drew Petzold
★★★★★4 months ago

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…

John Hannan
★★★★★10 months ago

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…

Tammy Mcguire
★★★★★a year ago

I was traveling for work and found this great cozy spot to eat! I like restaurants that are local to the area they're in. Winston's Cafe did not disappoint! I came in, sat down, I was greeted promptly, I already checked out the menu online and I ordered right away. The french…

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