Sir Winston Wine Loft & Restaurant

3.6

359 Reviews

$31 to $50

European

Make a booking

2 people

17 Mar 2025

19:00

Booked 4 times today

Charming
Good for special occasions
Good for business meals

Sir Winston serves as the reincarnation of the Original Sir Winston restaurant,
which occupied our space from 1967 until the 1990s in what was then The
Pepper Building, one of the most popular gathering places in the city. The
modern Sir Winston is a new kind of restaurant for a new kind of Winston-Salem.
Utilizing a farm-to-table philosophy, we offer exquisitely prepared local food in a
world-class setting for breakfast, brunch or dinner. In an environment of casual
elegance, we give diners the perfect place to enjoy a meal in the company of
friends, fellow diners and our attentive staff.
To honor Sir Winston Churchill’s love of fine food, our European-fusion menu
features international favorites from various countries that he frequented while
serving as Prime Minister.

Order delivery or takeout

Dining areas

Additional information

Dining style
Casual Elegant
Price
$31 to $50
Cuisines
European, International
Hours of Operation
Brunch Sat, Sun 06:30–15:00 Breakfast Mon–Fri 06:30–10:30 Bar Mon–Thu 17:00–23:00 Fri, Sat 14:00–00:00 Sun 10:00–22:00 Dinner Daily 17:00–22:00
Phone number
(336) 722-0795
Website
http://sirwinstonrestaurant.com/
Payment Options
AMEX, Discover, Mastercard, Visa
Dress code
Casual Dress
Executive Chef
Matthew Bertoni
Private party facilities
Our Restaurant and Wine Loft are available for private events as well. For reservations of parties of 8 or more guests, please visit https://sirwinstonrestaurant.com/events/

Location
104 W 4th St Winston, Salem, NC 27101
Area
Winston-Salem
Cross Street
4th and Liberty
Parking details
Valet
Additional
Banquet, Bar/Lounge, Beer, Cocktails, Corkage Fee, Counter Seating, Entertainment, Full Bar, Gluten-free Options, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Private Room, Takeaway, Weekend Brunch, Wheelchair Access, Wine

Sir Winston serves as the reincarnation of the Original Sir Winston restaurant, which occupied our space from 1967 until the 1990s in what was then The Pepper Building, one of the most popular gathering places in the city. The modern Sir Winston is a new kind of restaurant for a new kind of Winston-Salem. Utilizing a farm-to-table philosophy, we offer exquisitely prepared local food in a world-class setting for breakfast, brunch or dinner. In an environment of casual elegance, we give diners the perfect place to enjoy a meal in the company of friends, fellow diners and our attentive staff. To honor Sir Winston Churchill’s love of fine food, our European-fusion menu features international favorites from various countries that he frequented while serving as Prime Minister

Appetizers

Bread Service
Warm sourdough and rosemary bread with creamy butter and sprinkled with French sea salt.
Steak Tartare
Fresh beef tartare with capers, egg yolk, house pickles, and sourdough toast. Pairs well with Matsu "El Picaro" Tempranillo, Spain
Vegetable Samosa
Three (3) classic crispy Indian starters filled with a savory medley of spiced vegetables and mint cilantro chutney. Pairs well with J. Baumer Riesling, Germany
Spanish-Style Prawns
Whole grilled prawns tossed in a bold, vibrant mojo de ajo sauce, infused with garlic and spices. Pairs well with Campo de Borja Garnacha Blanca, Spain
Fritto Misto
Crispy golden-fried calamari served with lemon, pickled cherry peppers and remoulade sauce. Pairs well with Raw Bar Vinho Verde, Portugal
Arancini
Creamy, crispy risotto balls with a gooey center, served with house red sauce. Pairs well with La Torre Pinot Grigio, Italy
Lobster Bisque
Rich, velvety lobster bisque infused with aromatic herbs and a touch of cream. Pairs well with Ramsay Chardonnay, California

Entrees

Beef WellingtonUS$55.00
Beef wrapped in savory mushroom duxelles, crispy bacon, and golden puff pastry, infused with aromatic herbs. Pairs well with Quilt Cabernet Sauvignon, Napa Valley, California
LasagnaUS$22.00
Four layers of slow-cooked Bolognese, creamy ricotta, and velvety béchamel, infused with our signature herb blend. Pairs well with Grand Jean Bordeaux Superiore, France
CarbonaraUS$24.00
Spaghetti tossed in a creamy egg yolk sauce with smoky Harmony Ridge Farms bacon, topped with grated Pecorino Romano. Pairs well with Chateau de Chaintre Chardonnay, France
Char Grilled OctopusUS$13.00
Tender octopus with vibrant romesco sauce, served over chickpea salad with arugula, cherry tomatoes, feta, cucumbers, and onions, finished with a herb vinaigrette. Pairs well with Sassi Pinot Grigio, Italy
- AppetizerUS$13.00
- EntreeUS$19.00
BranzinoUS$24.00
Charred Mediterranean sea bass dusted with a vibrant green tahini sauce, served on a fresh herb salad, accompanied by crispy fingerling potatoes. Pairs well with Campo de Borja Garnacha Blanca, Spain
Sir Winston Deluxe BurgerUS$19.00
A blend of chuck, brisket, and short rib topped with cheddar cheese, lettuce, onion, tomatoes, and our special house sauce on a toasted bun, accompanied by crispy fries. Pairs well with Austin Cabernet Sauvignon, California
Bangers & MashUS$22.00
Juicy Jolly Posh English Bangers served alongside buttery mashed potatoes and sweet green peas, all smothered with a rich onion gravy. Pairs well with Aventura Red Blend, Spain
Chicken Tikka MasalaUS$32.00
Marinated chicken breast simmered in a rich sauce topped with a blend of traditional Indian spices, served alongside basmati rice and a generous helping of warm naan bread. Pairs well with TheoLeo Sauvignon Blanc, California
Veal ParmesanUS$24.00
A breaded and fried veal cutlet generously topped with melted mozzarella cheese and bathed in our signature red sauce, served on a bed of rigatoni. Pairs well with Matsu "El Picaro" Tempranillo, Spain
Piri Piri ChickenUS$18.00
Roasted half chicken slathered in our signature piri piri-style pepper sauce and served with salad and crispy rosemary fries. Pairs well with Haymaker Sauvignon Blanc, New Zealand
Steak FritesUS$48.00
A juicy Cabre Bon-in ribeye steak grilled to your desired temperature, topped with a rich pepper sauce, and served with crispy fries. Pairs well with Sokol Blosser Evolution Pinot Noir, Oregon

Salads

Caesar SaladUS$14.00
Crisp romaine lettuce tossed in our creamy house-made dressing topped with croutons & shaved Parmesan. (optional addition of anchovies)
Nicoise SaladUS$18.00
Tender chunks of tuna, potatoes, green beans, hard-boiled eggs, olives, & tomatoes nestled on a bed of spring mix & drizzled with a tangy Dijon vinaigrette
Spring Mix SaladUS$14.00
A delightful medley of local mixed lettuces, crisp carrots, and fresh radishes, all tossed in our house vinaigrette.

A La Carte

Pomme FritesUS$8.00
Basmati RiceUS$6.00
Fingerling PotatoesUS$7.00
Mashed PotatoesUS$6.00
Sautéed SpinachUS$6.00
Grilled AsparagusUS$7.00

Desserts

Guinness Chocolate CakeUS$9.00
Rich, indulgent, and infused with the depth of Guinness. Served warm with a scoop of vanilla ice cream
TiramisuUS$8.00
Layers of coffee-soaked ladyfingers and mascarpone, topped with a generous dusting of cocoa powder.
Panna CottaUS$8.00
A smooth custard, served with a selection of seasonal fruits.

What 359 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

3.6

3.6 based on recent ratings

3.7Food
4Service
4.1Ambience
3.5Value

Noise • Moderate

Loved For

Greensboro / Winston Salem / Highpoint
Lively
Winston Salem
Great for brunch
Winston Salem
Good for groups
Winston Salem
Romantic
Winston Salem
Lively

Review summary

AI-generated from verified diner reviews

Sir Winston Wine Loft & Restaurant offers a delightful dining experience with "fantastic food and service" and a "beautiful atmosphere." Diners rave about the "homemade tiramisu" and "smoked cocktails." Despite occasional issues with service speed, the "friendly staff" and "impressive menu" make it a popular choice.

359 Reviews

OT
OpenTable Diner
Greensboro2 reviews
3.0
Dined on 22 February 2025
1. Overall 3
2. Food 5
3. Service 1
4. Ambience 3
The food was delicious but for there to be only one other table being waited on and it took over an hour for us to get our food / drinks etc was ridiculous , but I would be up for trying again .
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S
Sunita
Charlotte4 reviews
4.0
Dined on 15 February 2025
1. Overall 4
2. Food 3
3. Service 4
4. Ambience 4
Our hostess was great, server good. We decided on this location due to the online menu and reviews. The actual menu at the restaurant was missing some items on the online menu. We were not impressed with the few food items we ordered and decided to just stick to drinks. It’s worth a try but we were slightly disappointed.
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G
Gabriel
West Virginia5 reviews
3.0
Dined on 15 February 2025
1. Overall 3
2. Food 3
3. Service 5
4. Ambience 5
Great atmosphere, great service, very friendly. The food was just average.
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D
Dustin
Charleston1 review
1.0
Dined on 15 February 2025
1. Overall 1
2. Food 2
3. Service 1
4. Ambience 3
Ambience was nice. Food came out lukewarm warm and not seasoned. Had to bask for salt and waited 10 minutes. Waitress never checked on us and we had to grab her to ask for more drink. Not the experience you expect for a $200 meal. For the money this was not worth it all!!!!!
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T
Terry
Greensboro18 reviews
2.0
Dined on 15 February 2025
1. Overall 2
2. Food 2
3. Service 3
4. Ambience 3
The place is retro 1950’s look which is nice. My wife’s steak was undercooked and had to send it back. The lobster bisque was like warm water not a bisque. The potatoes were barely warm but tasted good. The beet salad was the best thing. This was valentines and I was hoping for a special night out and it was not. And for 176 bucks that was pathetic. And we had valet park our car they couldn’t find it. Took 30 minutes of waiting to finally get it.
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B
Brooke
Greensboro1 review
5.0
Dined on 14 February 2025
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
We enjoyed the food and atmosphere. Our service was excellent. Can’t wait to go back!
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R
Rachel VIP
Atlanta2 reviews
5.0
Dined on 9 February 2025
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
Had a wonderful brunch with friends from out of town. Cocktail selection was extensive and lovely. The entire experience was enjoyed by all of us.
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M
Mark
Greensboro1 review
5.0
Dined on 5 January 2025
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 5
The waitstaff were very friendly and accommodating. The food was delicious and seasoned perfectly.
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L
Linda
Tampa3 reviews
5.0
Dined on 30 December 2024
1. Overall 5
2. Food 5
3. Service 5
4. Ambience 4
Our waiter Ryan was fantastic, and the food was delicious.
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C
Cay
Greensboro4 reviews
4.0
Dined on 25 December 2024
1. Overall 4
2. Food 4
3. Service 5
4. Ambience 3
Food was delicious. We had a prix fixe Christmas menu and it accomodated vegetarian and gluten free diets (not vegan) but their usual menu has more options, I'm sure. The outstanding moment was the 'mistletoe old fashioned'. It was possibly the best old fashioned I've ever had and it came out in its own humidor, which was a fun and excellent touch. The prices are high for Winston Salem so this will not be a staple for me but it checked all of the boxes for an extravagant, occassional experience.
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FAQs

Sir Winston Wine Loft & Restaurant offers takeout which you can order by calling the restaurant at (336) 722-0795.

Sir Winston Wine Loft & Restaurant is rated 3.6 stars by 359 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a booking

2 people

17 Mar 2025

19:00

Booked 4 times today

Order delivery or takeout

Google Map for Sir Winston Wine Loft & Restaurant

104 W 4th St Winston, Salem, NC 27101

Dining areas

Additional information

Cross Street
4th and Liberty
Area
Winston-Salem
Hours of Operation
Brunch Sat, Sun 06:30–15:00 Breakfast Mon–Fri 06:30–10:30 Bar Mon–Thu 17:00–23:00 Fri, Sat 14:00–00:00 Sun 10:00–22:00 Dinner Daily 17:00–22:00
Price
$31 to $50
Cuisines
European, International
Dining style
Casual Elegant
Dress code
Casual Dress
Parking details
Valet
Payment Options
AMEX, Discover, Mastercard, Visa
Executive Chef
Matthew Bertoni
Additional
Banquet, Bar/Lounge, Beer, Cocktails, Corkage Fee, Counter Seating, Entertainment, Full Bar, Gluten-free Options, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Private Room, Takeaway, Weekend Brunch, Wheelchair Access, Wine

Website
http://sirwinstonrestaurant.com/
Phone number
(336) 722-0795
Private party facilities
Our Restaurant and Wine Loft are available for private events as well. For reservations of parties of 8 or more guests, please visit https://sirwinstonrestaurant.com/events/

Sir Winston Wine Loft & Restaurant

Make a booking

Order delivery or takeout

Dining areas

Additional information

Appetizers

Bread Service

Steak Tartare

Vegetable Samosa

Spanish-Style Prawns

Fritto Misto

Arancini

Lobster Bisque

Entrees

Beef WellingtonUS$55.00

LasagnaUS$22.00

CarbonaraUS$24.00

Char Grilled OctopusUS$13.00

BranzinoUS$24.00

Sir Winston Deluxe BurgerUS$19.00

Bangers & MashUS$22.00

Chicken Tikka MasalaUS$32.00

Veal ParmesanUS$24.00

Piri Piri ChickenUS$18.00

Steak FritesUS$48.00

Salads

Caesar SaladUS$14.00

Nicoise SaladUS$18.00

Spring Mix SaladUS$14.00

A La Carte

Pomme FritesUS$8.00

Basmati RiceUS$6.00

Fingerling PotatoesUS$7.00

Mashed PotatoesUS$6.00

Sautéed SpinachUS$6.00

Grilled AsparagusUS$7.00

Desserts

Guinness Chocolate CakeUS$9.00

TiramisuUS$8.00

Panna CottaUS$8.00

Overall ratings and reviews

Loved For

Review summary

FAQs

Does Sir Winston Wine Loft & Restaurant offer delivery through OpenTable or takeout?

How is Sir Winston Wine Loft & Restaurant restaurant rated?

Is Sir Winston Wine Loft & Restaurant currently accepting bookings?

Make a booking

Order delivery or takeout

Dining areas

Additional information