Winston’s Cafe Menu Prices

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Welcoming, casual hangout featuring classic & creative American eats, live music & cocktails.

Winston’s Cafe is one of the first businesses in now booming Greenbrier. A hidden gem, we serve fresh, quality made to order Americana food highlighted by different daily chalkboard lunch and dinner specials.
Winston’s has committed to supporting local and regional music acts since its inception in 1990. We pride ourselves in going above and beyond to provide excellent customer service, making it your ultimate, local casual dining experience.
Come see why we’ve been a locals favorite in the community for almost 30 years!

  4.4 – 564 reviews  $$ • Restaurant

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Menu

Menu
APPETIZERS
Winston’s Jumbo Wings
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.		 $15.00
Lumpia
Beef lumpia, hand rolled in an authentic Filipino kitchen. Deep fried and served with a sweet and spicy chili sauce.		 $9.00
Steamed Shrimp
Large shrimp steamed in Old Bay, lemon and seasonal local, craft beer. 1/2# -$11 1# -$19		 $11.00
*Ahi Cajun Tuna Bites
Fresh Ahi Tuna rolled in a blend of Cajun seasoning, seared to your desired temperature and served with a roasted red pepper aioli.		 $12.00
Crab Spinach Dip
Lump crab meat folded into a blend of cheeses and baby spinach, then oven bakes. Served with a French loaf.		 $13.00
Seafood Quesadilla
A flour tortilla stuffed with our house made crab and spinach dip, grilled shrimp, mixed cheese. Served with salsa and sour cream.		 $14.00
Winston’s Nachos
Crisp tortilla chips piled with our house made chili, cheese blend, shredded lettuce, jalapeños, onions and tomatoes. Served with salsa and sour cream.		 $13.00
*Steak Bites
6oz. Of juicy steak cooked to your desired temperature and sprinkled with Cajun seasoning. Served with A1 steak sauce.		 $12.00
Chicken Tenders
Breaded chicken tenderloins served with your choice of dipping sauce or tossed in buffalo.		 $10.00
Mozzarella Sticks
5 thick cut, battered and deep fried. Served with marinara.		 $9.00
Loaded Fries
Our crispy fries topped with chili, bacon, mixed cheese and jalapeños.		 $11.00
Large Fries $6.00
Onion Rings $8.00
SOUPS
Deb’s Famous Potato Soup
Our hearty and creamy potato soup topped with shredded cheese and bacon crumbles. Cup $4 Bowl $5		 $4.00
French Onion Soup
A classic favorite topped with toasted French Brad and melted provolone. Cup $5 Bowl $6
Winston’s Chili
Our house made chili topped with Monterey Jack cheese and served with tortilla chips. Cup $5 Bowl $6		 $5.00
Soup of the Day
Try one of our awesome home made soups! -Market
Salads
House Salad
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		 $8.00
Cobb Salad
Fresh mixed greens topped with grilled chicken, diced bacon, hard boiled eggs, avacado, tomatoes, red onions, cucumbers and bleu cheese crumbles.		 $11.00
Caeser Salad
Fresh romaine lettuce with ages parmesan cheese and seasoned croutons. Tossed in a creamy Caeser dressing.		 $8.00
Gary Salad
Mixed greens, blackened chicken breast, fresh feta, sliced almonds, craisens, fresh fruit, tomatoes, onions and cucumbers.		 $15.00
Buffalo Chicken Salad
Our House salad topped with breaded chicken tenderloins, tossed in a mild wing sauce.		 $12.00
Burgers
*Hamburger
1/2# hand pattied, fresh ground beef burger. Add additional topping $1 each: cheese, fried egg, jalapeño, chili, bacon, sautéed mushrooms, sautéed onions.		 $9.00
*Winston’s Burger
1/2# burger topped with lump crab meat, bacon and provolone cheese.		 $14.00
Sandwiches/Wraps
French Dip
A Winston’s legend!! Thinly sliced rare roast beef and Swiss cheese, toasted on a French roll, served with hot Au Jus for dipping.		 $12.00
Winston’s Wonder
Roasted Turkey breast topped with bacon and melted Swiss, lettuce and tomatoes in a brioche roll.		 $11.00
NC Pulled Pork BBQ
Cooked low and slow, piled high and served with our homemade Carolina BBQ sauce.		 $9.00
Cranberry Walnut Chicken Salad
Fresh all white meat chicken salad with walnuts, cranberries and fresh baby spinach and tomato on a brioche roll.		 $11.00
Crispy Chicken Wrap
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!		 $12.00
*Ahi Tuna Wrap
Fresh Ahi Tuna cooked to your liking with lettuce, tomatoes, shredded cheese and a roasted red pepper aioli. Wrapped in a grilled flour tortilla.		 $13.00
Hot Italian
Layers of hard salami, sliced ham and melted provolone, topped with onions, lettuce and tomatoes. Finished with Italian dressing on a toasted French roll.		 $11.00
Pastrami Reuben
Fresh sliced Pastrami, Swiss cheese, sauerkraut and 1,000 island dressing on grilled marble rye.		 $12.00
Philly Sub
(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.		 $12.00
Crabcake Sammy
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.		 $13.00
*English Dip
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		 $14.00
Club Sandwich
Layers of turkey, ham, bacon, Swiss and American cheese, lettuce, tomatoes between 3 slices of marble rye or Texas toast.		 $13.00
Chicken Parmesan
Breaded Chicken breast, topped with marinara and mozzarella cheese on a brioche roll.		 $11.00
Entree’s
*Prime Rib
12oz slow roasted USDA choice prime rib, hand cut and cooked to your desired temperature, served with hot Au Jus.		 $25.00
*Black and Bleu Ribeye
Tender 12oz hand-cut ribeye grilled with blackened seasoning, topped with your choice of bleu cheese crumbles or sautéed mushrooms and onions.		 $26.00
*Ribeye Steak
12 oz hand cut ribeye seasoned and grilled to desired temperature.		 $25.00
*Winstons Surf and Turf
Hand cut 6oz flat iron paired with your choice of Tuna, Crabcake, grilled shrimp or our salmon		 $22.00
Crabcake Dinner
Two of the Chef’s signature lump crab cakes, broiled or fried to a golden brown, served with tarter or cocktail.		 $24.00
Chicken Parmesan
Tender chicken breast, topped with mozzarella and served with a side of pasta and marinara.		 $14.00
Creamy Cajun Alfredo
Penne pasta tossed with peppers and broccoli oki in a Cajun Alfredo cream sauce. *Add chicken $5 • Add grilled shrimp $6		 $11.00
Children’s Menu
Grilled Cheese, chicken tenders or 1/4 cheeseburger, served with a choice of sliced apple, veggies, chips or fries. $6.00

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Menu Photos

Contact Winston’s Cafe

Address: 1412 Greenbrier Pkwy #133, Chesapeake, VA 23320

Phone: (757) 420-1751

Website: http://winstons-cafe.business.site/

Social Profile:

Hours

Sunday Closed
Monday 11AM–11PM
Tuesday 11AM–11PM
Wednesday 11AM–11PM
Thursday 11AM–11PM
Friday 11AM–11PM
Saturday 11AM–11PM

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