What should I order at Winston's Cafe?
Winston's Cafe
French Dip Sandwich
Most frequently praised item in the reviews; described as fantastic, very good, and even the best some reviewers have ever had. Reviewers loved the tender roast beef, great cheese, and well-made au jus.
Burger
Recommended multiple times across different reviews, including the Texas Burger and a general burger order. Reviewers said the burgers were piping hot, absolutely delicious, and even rated one burger 10 out of 10.
Meatloaf Lunch Special
Mentioned positively for being hearty and homestyle, with one reviewer saying their mom loved it. It was especially praised for its flavor and for not being topped with ketchup like at some other places.
Mac And Cheese
Called delicious, creamy, fresh, and made to order. Reviewers highlighted it as a standout side dish worth coming back for.
Potato Salad
Strongly recommended because it was described as homemade and one reviewer said it was literally the best they had ever tasted.
Prime Rib
Included among the standout dishes in a highly positive review, praised as part of the restaurant’s top-notch food quality.
Hours
| Monday | 11 AM to 10 PM |
|---|---|
| Tuesday | 11 AM to 10 PM |
| Wednesday | 11 AM to 10 PM |
| Thursday | 11 AM to 12 AM |
| Friday | 11 AM to 12 AM |
| Saturday | 11 AM to 12 AM |
| Sunday | 11 AM to 8 PM |
About Winston's Cafe
Welcoming, casual hangout featuring classic & creative American eats, live music & cocktails.
Amenities & services
From the business
- Identifies as women-owned
Service options
- Curbside pickup
- Delivery
- Onsite services
- Takeout
- Dine-in
Highlights
- Fast service
- Great beer selection
- Great cocktails
- Live music
- Serves local specialty
- Sports
Popular for
- Lunch
- Dinner
- Solo dining
Accessibility
- Wheelchair accessible entrance
- Wheelchair accessible parking lot
- Wheelchair accessible restroom
- Wheelchair accessible seating
Offerings
- Alcohol
- Beer
- Cocktails
- Coffee
- Comfort food
- Happy hour drinks
- Happy hour food
- Hard liquor
- Healthy options
- Late-night food
- Quick bite
- Small plates
- Wine
Dining options
- Brunch
- Lunch
- Dinner
- Catering
- Dessert
- Seating
- Table service
Amenities
- Bar onsite
- Restroom
- Wi-Fi
- Free Wi-Fi
Atmosphere
- Casual
- Cozy
- Trendy
Crowd
- Family-friendly
- Groups
- LGBTQ+ friendly
Planning
- Accepts reservations
Payments
- Credit cards
- Debit cards
- NFC mobile payments
- Credit cards
Children
- Good for kids
- High chairs
- Kids' menu
Parking
- Free parking lot
- Free street parking
- Usually plenty of parking
Frequently asked questions
What is Winston's Cafe known for?
Winston's Cafe is especially known for its French dip sandwich, which reviewers repeatedly call one of the best they have had, including for takeout and delivery. The prime rib is another standout, along with hearty burgers and comfort-food plates that arrive hot and well prepared.
What dishes are most recommended at Winston's Cafe?
The most recommended items are the French dip, prime rib, Texas Burger, Mushroom Swiss Burger, and Winston Wonder. Reviewers also highlight the meatloaf lunch special, meatball sub, crab dip, chicken parmesan, and the wings and mac and cheese during happy hour.
What is the atmosphere like at Winston's Cafe?
The vibe is casual, cozy, and a little trendy, with a narrow dining room, a small full bar, and live music or trivia nights. It seems to work well for groups, solo diners, and people looking for a relaxed local spot with sports, cocktails, and a friendly staff.
Is Winston's Cafe good value, and what is the price range?
The price range is $10 to $20, which matches the hearty portions and comfort-food menu that reviewers describe as filling and worth the cost. Happy hour is a value draw too, with a $.79 wing deal available daily from 3 to 7 pm.
When is a good time to visit Winston's Cafe?
Reviewers mention that around 3:30 pm the dining room was not busy, while parking can fill up at busier times in the Crossways Shopping Center area of Chesapeake. If you want a quieter visit, an off-peak afternoon seems easier, but happy hour from 3 to 7 pm is when the wing deal is available.
Is parking available at Winston's Cafe?
Yes. Free parking lot, Free street parking, Usually plenty of parking is available.
Is Winston's Cafe kid-friendly?
Yes, Winston's Cafe is good for kids.
Restaurants like Winston's Cafe in Chesapeake
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