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Welcome to Winston's Cafe

Winston's Cafe, located at 1412 Greenbrier Pkwy in Chesapeake, VA, is a cozy dining gem celebrated for its flavorful dishes and warm service. Patrons rave about the diverse menu, with standouts like the chicken salad and crab and shrimp Alfredo. The inviting atmosphere fosters a sense of community, where returning customers feel like regulars from the moment they walk in. Highlights include an unbeatable .79 wing deal during happy hours and freshly made mac and cheese that never disappoints. Winston's Cafe embraces a down-to-earth charm, prioritizing great food and genuine hospitality over trendy decor, making it a must-visit for food lovers.

Winston's Cafe: Reviews & Ratings

Ruth
Ruth

The food was so good that me and my husband came back that same week. Had a great server Stephanie on our first visit. The server on the second visit was great too, I’m sorry I can’t remember your name but you were great too. Overall I was surprised how flavorful the food was. The setting isn’t anything fancy like those instagramable places but the food and service was amazing. I’ll take great food and service over a random flower wall any day.

Fonzy F
Fonzy F

Cozy hole in the wall Had the flounder basket, it was delicious. My server was great, made me feel like a regular and I'm from out of town. Highly recommend. The breakfast beer was a better version of Guinness.

Matea L.
Matea L.

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.

Ryan Riffle
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

Sierrah Smiles
Sierrah Smiles

Might have found my new hang out spot. I was a single diner and, while that can be awkwardly at times, my waitress made me feel welcome. Had that southern kindness that goes a long way. I got the crab and shrimp Alfredo and a side of fries. The Alfredo was amazing. A little salty for me, but I have that issues at a lot of places. I’m excited to try more of their food after today!

Willie Porche
Willie Porche

Simply an amazing restaurant to eat at. The food, the atmosphere, and the service are all top-notch. From the delicious prime rib to the meaty club sandwich, the amazing Ruben. I honestly can't wait to come back. The absolute only issue was I ate too much. I just couldn't stop.

Kaszia C.
Kaszia C.

Woooooonderful dive bar we rolled up on just checking out the area. Our bartender was fantastic! They also have an open mic night. The food, drinks, and service all grade A!

Tammy Mcguire
Tammy Mcguire

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 dip sandwich was fantastic, and I am always looking for a good French dip. It was also trivia night and I was seated a bit far, but the host came over and made sure I felt included which I thought was very nice touch! I will definitely go back the next time I'm in that area!

Location

  • Winston's Cafe
    1412 Greenbrier Pkwy #133, Chesapeake, VA 23320, United States Hotline: +1 757-420-1751

Welcome to Winston's Cafe, a hidden gem nestled at 1412 Greenbrier Pkwy #133, Chesapeake, VA. This cozy spot has quickly built a reputation for its delightful dishes and warm hospitality, making it a must-visit for locals and travelers alike. With an inviting atmosphere, Winston's offers a refreshing escape from the hustle and bustle, where the focus is on serving quality food over flashy decor.

As I stepped inside Winston's, I was greeted by the friendly staff who aim to make every guest feel right at home. One highlight of this cafe is undoubtedly its food. The flavors are vibrant and memorable, with each dish prepared with care. From the flounder basket that received rave reviews for its deliciousness to the chicken salad that continues to win hearts, there are options to satisfy every palate.

Bite into their French dip sandwich or indulge in the creamy, made-to-order mac and cheese—both dishes praised for their fantastic taste. For those looking to unwind, stop by during happy hour for their incredible wing deals that keep patrons coming back, day after day.

The reviews say it all. Customers rave about the quick service and the staff's caring approach, reflecting a level of southern hospitality that lingers long after the meal. Perhaps it’s the crab and shrimp Alfredo, which promised indulgence, or the comfort of a solo meal, where the waitstaff goes above and beyond to ensure every diner feels welcome. Winston's Cafe isn't just a place to eat; it’s a space to connect over shared experiences and great food.

If you’re in the Chesapeake area, make your way to Winston's Cafe—where every visit feels like a homecoming, and every meal is a celebration of flavor and friendship.