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Winston's Cafe — Restaurant in Chesapeake

Name
Winston's Cafe
Description
Welcoming, casual hangout featuring classic & creative American eats, live music & cocktails.
Nearby attractions
Nearby restaurants
Rajput Indian Eats
1412 Greenbrier Pkwy #135, Chesapeake, VA 23320
Smokey Bones Chesapeake
1405 Greenbrier Pkwy, Chesapeake, VA 23320
Kyoto Japanese Steakhouse & Sushi Bar
1412 Greenbrier Pkwy, Chesapeake, VA 23320
HotPot 757 Chesapeake
1412 Greenbrier Pkwy #121, Chesapeake, VA 23320
Ruby Tuesday
1412 Greenbrier Pkwy #130, Chesapeake, VA 23320
Pho Dalat
836 Eden Way N, Chesapeake, VA 23320
Smashburger
1412 Greenbrier Pkwy, Chesapeake, VA 23320
Pop's Diner Co.
1432 Greenbrier Pkwy, Chesapeake, VA 23320
Famous Uncle Al's
1412 Greenbrier Pkwy #116, Chesapeake, VA 23320
Kelly's Tavern
1412 Greenbrier Pkwy, Chesapeake, VA 23320
Nearby hotels
Tru by Hilton Chesapeake Greenbrier
1570 Crossways Blvd, Chesapeake, VA 23320
Homewood Suites by Hilton Chesapeake-Greenbrier
1569 Crossways Blvd, Chesapeake, VA 23320
Hilton Garden Inn Chesapeake/Greenbrier
1565 Crossways Blvd, Chesapeake, VA 23320
Hyatt Place Chesapeake/Greenbrier
709 Eden Way N, Chesapeake, VA 23320
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd, Chesapeake, VA 23320
Courtyard by Marriott Chesapeake Greenbrier
1562 Crossways Blvd, Chesapeake, VA 23320
Fairfield by Marriott Inn & Suites Chesapeake
1560 Crossways Blvd, Chesapeake, VA 23320
Extended Stay America Suites- Chesapeake - Crossways Blvd.
1540 Crossways Blvd, Chesapeake, VA 23320
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Keywords
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Winston's Cafe things to do, attractions, restaurants, events info and trip planning
Winston's Cafe
United StatesVirginiaChesapeakeWinston's Cafe

Basic Info

Winston's Cafe

1412 Greenbrier Pkwy #133, Chesapeake, VA 23320
4.4(397)
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Ratings & Description

Info

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

attractions: , restaurants: Rajput Indian Eats, Smokey Bones Chesapeake, Kyoto Japanese Steakhouse & Sushi Bar, HotPot 757 Chesapeake, Ruby Tuesday, Pho Dalat, Smashburger, Pop's Diner Co., Famous Uncle Al's, Kelly's Tavern
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Phone
(757) 420-1751
Website
winstonscafe.com

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Featured dishes

View full menu
dish
Ahi Cajun Tuna Bites
dish
Crab Spinach Dip
dish
Seafood Quesadilla
dish
Chicken Tenders
dish
French Onion Soup
dish
Cranberry Walnut Chicken Salad
dish
Hot Italian
dish
Club Sandwich
dish
Chicken Parmesan
dish
Chicken Parmesan

Reviews

Things to do nearby

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Nearby restaurants of Winston's Cafe

Rajput Indian Eats

Smokey Bones Chesapeake

Kyoto Japanese Steakhouse & Sushi Bar

HotPot 757 Chesapeake

Ruby Tuesday

Pho Dalat

Smashburger

Pop's Diner Co.

Famous Uncle Al's

Kelly's Tavern

Rajput Indian Eats

Rajput Indian Eats

4.8

(436)

Click for details
Smokey Bones Chesapeake

Smokey Bones Chesapeake

4.4

(2.1K)

$$

Open until 1:00 AM
Click for details
Kyoto Japanese Steakhouse & Sushi Bar

Kyoto Japanese Steakhouse & Sushi Bar

4.1

(417)

Click for details
HotPot 757 Chesapeake

HotPot 757 Chesapeake

4.6

(599)

Click for details
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Reviews of Winston's Cafe

4.4
(397)
avatar
5.0
2y

We went to Winston's after walking out of Kelly's tavern because lack of service was ridiculous. Had a couple people at booths, and a smallish group at the bar watching football. Seat yourself, we sat down, waitress came by acknowledged us, and was pretty busy. Not sure if she was also tending bar. Brought us drinks and went to other table, apparently double sat, we were 2nd. But the fact she acknowledged us, made it ok. She got their orders and came back to us for our order, they had several running specials. We got Lumpia app/special. It was ready super fast, and was really good, excellent dipping sauce was perfect, spicey and sweet. I ordered the Pastrami Reuben, w brown mustard, (which incidentally, I'd wanted at Kelly's, but they only had it in corn beef). My friend got the French Dip. As we sat more people started coming in, and restaurant closes at 8, we went in at 7. But they stayed open to accommodate the new customers. That in itself shows they care about the staff too. Service was awesome, she was SLAMMED by that point and the only waitress, but knew what she was doing, very experienced. Recognized when drinks were low, came by when she had a chance immediately after seeing that, even though she had a full booth area and full bar area! As former servers, we know good service and we appreciate it! This had it all. Casual, American fare, bar food w some entrees that looked good too. We have a small shop in Midlothian and have to do this route often on Sundays, now we have a place to stop for good food, good service, on way home to VB if time allows. Way better experience than Kelly's and likely way better food than what they offered. Highly recommend Winston's, SUPPORT LOCAL!...

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avatar
2.0
8y

this place came highly recommended from a family member. perhaps they were having a bad night . first visit didn't have lunch yesterday decided to check it out. First I guess a shortage of menu's given one for two people sitting across from one another. husband ordered the pork dinner. i ordered cranberry walnut chicken salad sandwich and sweet potato fries. Nice waitress. Ask for a second menu and then 10min later sorry sir no pork for dinner out. 10 more minutes sorry ma'am no sweet potato fries. My husband says lets leave. I say no we are already here. 15 or 20 more minutes go by no food. my husband had decided to get a philly sub nothing special but had thought of getting the prime rib special. 5 prime rib specials came out in a flash! wondering where are our two sandwiches starving. Finally got them both and chicken salad was ok but did not taste any cranberries or walnuts so i looked for them and called the waitress over again and ask where they were she once again apologized said i received the plain chicken incorrectly they had just had it on lunch special she later brought me another sandwich . I ate half and we left disappointed.First impressions are EVERYTHING!! We eat out all the time but won't rush back. The kitchen staff apologize and they reduced the cost by the drink amount. Personally it should have been free for the constant trouble. lost...

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avatar
2.0
1y

Poor service, don't know if you are a bar or restaurant, trying to eat but listening to heavy metal music and loud patrons us the f word. Broccoli steamed to mush with no seasoning. Fried shrimp without cocktail sauce.. crab and spinach dip that smelled like a old fish, shrimp pasta that had two pounds of pasta and 4 shrimp...over portions and over priced entrees. The fish special was more than the regular menu price. All entrees served with a house salad.. possibly two with a salad...waited longer to pay and leave than took to eat. Very understaffed. did no one review the new menu before it was printed what happened to the dark romantic restaurant that was packed with acoustic guitar. Change the name to Whatever from Winstons and it might catch back on. If you want to get those prices you need to do something different. I can't say much of anything good. It was very confusing to say the least.. sorry but you're going backwards. You cant accomplish anything by simply raising the price and adding more pasta and sauce. It's not working for me. But that's just me. I tried. I spent $116.00. not ever again. I'll try a appetizer first then decide to...

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Posts

M SM S
We visited Winston's Cafe on Greenbrier Parkway after work on a Friday evening. This was our first visit and you could tell this is a local spot but everyone made us feel welcome. The servers were super nice and knowledgeable about the food and drinks. We ordered garlic parmesan wings, crab & spinach dip and nachos. The wings were a little different from there usual garlic parmesan in that these were coated in powdered parmesan cheese. We also ordered drinks and the server was able to recommend a specialty martini with sliced strawberries- nice!! Everything was delicious. We will be back!!
Tammy McguireTammy 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!
Gordon WhitlockGordon Whitlock
You see a name like Winston’s Café, you think, hey I’ll go get some food. Well you can bank on getting some good food here. Service is very good. I appreciate everything about this place. Bar is a little bit smaller and has some good friends hanging out there all the time. On this particular day I rode right up and parked my motorcycle underneath the awning... Don’t do that because it’s really not permitted, I think I remember being told. LOL
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We visited Winston's Cafe on Greenbrier Parkway after work on a Friday evening. This was our first visit and you could tell this is a local spot but everyone made us feel welcome. The servers were super nice and knowledgeable about the food and drinks. We ordered garlic parmesan wings, crab & spinach dip and nachos. The wings were a little different from there usual garlic parmesan in that these were coated in powdered parmesan cheese. We also ordered drinks and the server was able to recommend a specialty martini with sliced strawberries- nice!! Everything was delicious. We will be back!!
M S

M S

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Get the Appoverlay
Get the AppOne tap to find yournext favorite spots!
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!
Tammy Mcguire

Tammy Mcguire

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You see a name like Winston’s Café, you think, hey I’ll go get some food. Well you can bank on getting some good food here. Service is very good. I appreciate everything about this place. Bar is a little bit smaller and has some good friends hanging out there all the time. On this particular day I rode right up and parked my motorcycle underneath the awning... Don’t do that because it’s really not permitted, I think I remember being told. LOL
Gordon Whitlock

Gordon Whitlock

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