Winston's Cafe Menu
45 items in 7 sections · $4.00 – $26.00 · Restaurant in Chesapeake, VA
Winston's Cafe’s menu lists 45 dishes and drinks, grouped into APPETIZERS, SOUPS, Salads, Burgers, Sandwiches/Wraps, and Entree’s and more. Prices range from $4.00 to $26.00, and a typical item costs about $12.00. Popular choices include Winston’s Jumbo Wings, Deb’s Famous Potato Soup, House Salad, *Hamburger, and French Dip.
APPETIZERS 13
- Winston’s Jumbo Wings$15.00
10 wings fried crispy and tossed in either mild or buffalo, garlic parmesan, old bay, Caribbean jerk, sweet and spicy chili, bbq or our signature big daddy sauce. Served with blue cheese or ranch dressing and celery.
- Lumpia$9.00
Beef lumpia, hand rolled in an authentic Filipino kitchen. Deep fried and served with a sweet and spicy chili sauce.
- Steamed Shrimp$11.00
Large shrimp steamed in Old Bay, lemon and seasonal local, craft beer. 1/2# -$11 1# -$19
- *Ahi Cajun Tuna Bites$12.00
Fresh Ahi Tuna rolled in a blend of Cajun seasoning, seared to your desired temperature and served with a roasted red pepper aioli.
- Crab Spinach Dip$13.00
Lump crab meat folded into a blend of cheeses and baby spinach, then oven bakes. Served with a French loaf.
- Seafood Quesadilla$14.00
A flour tortilla stuffed with our house made crab and spinach dip, grilled shrimp, mixed cheese. Served with salsa and sour cream.
- Winston’s Nachos$13.00
Crisp tortilla chips piled with our house made chili, cheese blend, shredded lettuce, jalapeños, onions and tomatoes. Served with salsa and sour cream.
- *Steak Bites$12.00
6oz. Of juicy steak cooked to your desired temperature and sprinkled with Cajun seasoning. Served with A1 steak sauce.
- Chicken Tenders$10.00
Breaded chicken tenderloins served with your choice of dipping sauce or tossed in buffalo.
- Mozzarella Sticks$9.00
5 thick cut, battered and deep fried. Served with marinara.
- Loaded Fries$11.00
Our crispy fries topped with chili, bacon, mixed cheese and jalapeños.
- Large Fries$6.00
- Onion Rings$8.00
SOUPS 4
- Deb’s Famous Potato Soup$4.00
Our hearty and creamy potato soup topped with shredded cheese and bacon crumbles. Cup $4 Bowl $5
- French Onion Soup
A classic favorite topped with toasted French Brad and melted provolone. Cup $5 Bowl $6
- Winston’s Chili$5.00
Our house made chili topped with Monterey Jack cheese and served with tortilla chips. Cup $5 Bowl $6
- Soup of the Day
Try one of our awesome home made soups! -Market
Salads 5
- House Salad$8.00
Mixed greens topped with cucumbers, tomatoes, red onions, mixed cheese and seasoned croutons. •Add chicken breast or chicken salad $5 •Sirloin Steak, Tuna Steak, Salmon, or Shrimp $6
- Cobb Salad$11.00
Fresh mixed greens topped with grilled chicken, diced bacon, hard boiled eggs, avacado, tomatoes, red onions, cucumbers and bleu cheese crumbles.
- Caeser Salad$8.00
Fresh romaine lettuce with ages parmesan cheese and seasoned croutons. Tossed in a creamy Caeser dressing.
- Gary Salad$15.00
Mixed greens, blackened chicken breast, fresh feta, sliced almonds, craisens, fresh fruit, tomatoes, onions and cucumbers.
- Buffalo Chicken Salad$12.00
Our House salad topped with breaded chicken tenderloins, tossed in a mild wing sauce.
Burgers 2
- *Hamburger$9.00
1/2# hand pattied, fresh ground beef burger. Add additional topping $1 each: cheese, fried egg, jalapeño, chili, bacon, sautéed mushrooms, sautéed onions.
- *Winston’s Burger$14.00
1/2# burger topped with lump crab meat, bacon and provolone cheese.
Sandwiches/Wraps 13
- French Dip$12.00
A Winston’s legend!! Thinly sliced rare roast beef and Swiss cheese, toasted on a French roll, served with hot Au Jus for dipping.
- Winston’s Wonder$11.00
Roasted Turkey breast topped with bacon and melted Swiss, lettuce and tomatoes in a brioche roll.
- NC Pulled Pork BBQ$9.00
Cooked low and slow, piled high and served with our homemade Carolina BBQ sauce.
- Cranberry Walnut Chicken Salad$11.00
Fresh all white meat chicken salad with walnuts, cranberries and fresh baby spinach and tomato on a brioche roll.
- Crispy Chicken Wrap$12.00
Crispy fried chicken tenderloins with bacon, Monterey Jack cheese, lettuce, tomatoes and ranch dressing, wrapped in a grilled flour tortilla. Add buffalo sauce for an extra kick!
- *Ahi Tuna Wrap$13.00
Fresh Ahi Tuna cooked to your liking with lettuce, tomatoes, shredded cheese and a roasted red pepper aioli. Wrapped in a grilled flour tortilla.
- Hot Italian$11.00
Layers of hard salami, sliced ham and melted provolone, topped with onions, lettuce and tomatoes. Finished with Italian dressing on a toasted French roll.
- Pastrami Reuben$12.00
Fresh sliced Pastrami, Swiss cheese, sauerkraut and 1,000 island dressing on grilled marble rye.
- Philly Sub$12.00
(Chicken or Beef) Shaved Ribeye steak or strips of grilled chicken breast sautéed with onions, green peppers, then covered with melted provolone and topped with lettuce and tomatoes.
- Crabcake Sammy$13.00
Our House made Crabcake fried or broiled on a toasted brioche roll with lettuce and tomato. Served with tarter or a roasted red pepper aioli.
- *English Dip$14.00
Our slow cooked choice Prime Rib cooked to temperature on a toasted French Roll, served with a side of hot Au Jus. Add Swiss or provolone $1
- Club Sandwich$13.00
Layers of turkey, ham, bacon, Swiss and American cheese, lettuce, tomatoes between 3 slices of marble rye or Texas toast.
- Chicken Parmesan$11.00
Breaded Chicken breast, topped with marinara and mozzarella cheese on a brioche roll.
Entree’s 7
- *Prime Rib$25.00
12oz slow roasted USDA choice prime rib, hand cut and cooked to your desired temperature, served with hot Au Jus.
- *Black and Bleu Ribeye$26.00
Tender 12oz hand-cut ribeye grilled with blackened seasoning, topped with your choice of bleu cheese crumbles or sautéed mushrooms and onions.
- *Ribeye Steak$25.00
12 oz hand cut ribeye seasoned and grilled to desired temperature.
- *Winstons Surf and Turf$22.00
Hand cut 6oz flat iron paired with your choice of Tuna, Crabcake, grilled shrimp or our salmon
- Crabcake Dinner$24.00
Two of the Chef’s signature lump crab cakes, broiled or fried to a golden brown, served with tarter or cocktail.
- Chicken Parmesan$14.00
Tender chicken breast, topped with mozzarella and served with a side of pasta and marinara.
- Creamy Cajun Alfredo$11.00
Penne pasta tossed with peppers and broccoli oki in a Cajun Alfredo cream sauce. *Add chicken $5 • Add grilled shrimp $6
Children’s Menu 1
- Grilled Cheese, chicken tenders or 1/4 cheeseburger, served with a choice of sliced apple,$6.00
Menu items and prices are provided for information and may have changed (last updated April 2026). Allergen information is not included – please ask the restaurant.