A Chef’s Table attendees tip their hat to Sir Winston
The Pepper Building no longer sits lonely and vacant. Years passed as many walked by wondering what would become of the 1928 art-deco landmark when it was announced several years ago that the building had been sold and would become a boutique hotel and restaurant.
Indigo Hotels, owned by IHG, like to spring up in areas that provide their guests with a more local experience. Sir Winston Restaurant & Wine Loft is located immediately inside of the hotel, and as soon as you walk in, you’re immersed in a local experience. From the walls adorned by local artists to Sunnyside Millworks’ handcrafted banquettes, tables, chairs and all of the new woodwork in the restaurant, the focus on those local details are quite obvious. The restaurant was at one time in the basement of the Pepper Building, and the new Sir Winston is a nod to its predecessor of the 1960s and its inspirational namesake, Sir Winston Churchill. People who have eaten at Sir Winston in the ’60s will see familiar quotes as well as light fixtures found in the sub-basement that have now been repurposed in the bar and dining room. The attention to detail is impeccable.
Chef David Swing was hired to design the menu and lead the kitchen of the new Sir Winston, which opened in the spring. Swing was born in Winston-Salem, grew up in Wilmington, gained his culinary skills in New York City, and worked his way back to the City of Arts and Innovation several years ago. To build the menu, he had to go all the way back to the late ’60s.
“I was given the original Sir Winston menu, and I took some ideas from that, but I had to assure management that I would not implement that pricing structure,” Swing joked.
(For context, the prime rib back in the day was $2.25.)
Sir Winston endeavors to take you back in time enough to appreciate classic details and flavors, but bring you back to today’s modern techniques, flair and Swing’s influence of Southern cuisine.
Swing took popular items such as seafood and prime rib and put his own spin on it.
“Shrimp cocktail was very popular, so I came up with Sutler’s Gin pickled-shrimp, which is on our small plates menu as well as on our N.C. trout dish.”
Swing said they didn’t want to be a steakhouse but did want red meat options on the menu.
“To play off the prime rib, all of our signature steaks come off the rib loin, which we break down in-house, including my personal favorite, the cap steak which is featured in the Bulldog’s cut.”

Course 1
Swing said this steak made the menu after he got his hands on the cookbook of Sir Winston Churchill’s personal cook. Between researching original menus and Churchill’s indulgences, writing and re-writing menus, Swing said he spent at least two months preparing for this gig.
Chef Swing introduced a few new ideas to the guests that will be featured on the upcoming fall menu, but the tasting courses were a great balance of the tastes of summer and a nod to the spiciness of fall.
Course One
Pimento Cheese-Stuffed Squash Blossom with Apricot Mango Chutney

Course 2
I love the delicate texture of a stuffed squash blossom that’s been flash-fried, and it seems like they were made for pimento cheese. This appetizer tasted like summertime in the South.
Course Two
Cinnamon Maple-Smoked Pork
Rind-Encrusted Chicken Lollipop
with Texas Pete Dust
This beautiful chicken drumstick was a conversation starter at most tables. The sauce was rich and robust, and the pork rind crust added another crispy dimension. I could see this dish on a menu anywhere, and it would be a fun lunch item- Swing must think so, too.

Course 3
“I’m playing with smoking Cornish hens and preparing them the same way, with bacon jam and the pork rind crust.”
Course Three
Seared Scallop, Pork Belly, Beet Purée with Pickled Watermelon

Course 4
Our very own version of surf and turf. I’ve enjoyed scallops, which are now on the menu at Sir Winston, and the culinary team prepares them to perfection.
Course Four
Seared N.C. Grouper, Black Truffle Risotto, Raspberry Mole with Blood Orange Purée
Sea dwellers twice in one night? What a lovely treat.

Course 5
Course Five
Cheerwine-Braised Boneless Short Rib with Chipotle Grits, Gremolata
This course was the most comforting of the night, and Swing said there is a variation now on the menu.
Course Six
Orange Ginger Cake with Wasabi Mousse
Beautifully presented, the orange and ginger on this petite cake were reminiscent of the coming season. The mousse on top was definitely adventurous, to say the least.
Sir Winston is a hotel-restaurant, but Swing said he appreciates the company’s approach to embracing the local story.
“It does have this corporate backing, but the fact that it’s a chef-driven restaurant and that they said to me, ‘Alright chef, here’s a very little direction and the ball is in your court,’ was something that I’d been looking for a long time.”
Kristi Maier is a food writer, blogger and cheerleader for all things local who even enjoys cooking in her kitchen, though her kidlets seldom appreciate her efforts.
Wanna go?
Sir Winston Restaurant & Wine Loft is located at 104 W. 4th St. in Winston-Salem.