Winston's Cafe
$ • American, New American, VegetarianAbout Winston's Cafe
Customers' Favorites
Cranberry Walnut Chicken Salad
Winston’S Jumbo Wings
Winston’S Jumbo Wings
Winston’S Burger
French Dip Sandwich
Winston’S Burger
Winston’S Nachos
French Onion Soup
Chicken Parmesan
Steamed Shrimp
Winston's Cafe Reviews
304 ratings
Share your opinion about Winston's Cafe
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 around then as well.
I wish I had names, especially for the amazing waitress who served us (she was blond, I know that!). I came in with my daughter and elderly father who has dementia. Dad wanted an egg sandwich. We had already driven by some of the usual breakfast spots and naturally...read full review
I wish I had names, especially for the amazing waitress who served us (she was blond, I know that!). I came in with my daughter and elderly father who has dementia. Dad wanted an egg sandwich. We had already driven by some of the usual breakfast spots and naturally...read full review
Winston’s is my go to place for a great meal. No matter the time of day or the day of the week! I can’t recommend this place enough.
The food was tasty. Our waitress was so friendly her service was amazing. Great prices and the food was hot and fast.
Hours
| Monday | 11AM - 10PM |
| Tuesday | 11AM - 10PM |
| Wednesday | 11AM - 10PM |
| Thursday | 11AM - 12AM |
| Friday | 11AM - 12AM |
| Saturday | 11AM - 12AM |
| Sunday | 11AM - 8PM |
Winston's Cafe in Chesapeake, VA, is a charming spot with a cozy atmosphere, perfect for a relaxed meal. The friendly and polite staff provide top-notch service, ensuring a pleasant experience. This hidden gem serves delicious housemade specialties, fresh sides, and a variety of beers on tap at reasonable prices. Diners have praised the amazing food, highlighting dishes like the wings and shrimp and crab pasta, which is known for being generous with crab. With regular live music and a welcoming vibe, it's a local favorite that's worth visiting for a casual lunch or special dinner. The cafe is a great choice for families, as it caters well to kids, ensuring everyone has a great meal. Regulars love the fresh, well-seasoned food and the variety of amazing specials, making it a must-try over chain restaurants. The small size of the cafe doesn't reflect the huge menu and everything being done well, as the locals have their own favorites. The staff, like Leah, are amazing and attentive, ensuring a wonderful experience for every visitor. The atmosphere, food, and live music make Winston's Cafe a beloved local gem that continues to impress customers.