Sir Winston is also the reincarnation of the Original Sir Winston restaurant,
which occupied our space from 1967 until the 1990s in what was then The Pepper Building. It was one of the most popular gathering places in the city for over two decades.
The Pepper Building in the 1930s
The entrance to the original Sir Winston Restaurant in The Pepper Building.
(Note: This photo was taken long after the restaurant had closed and prior to the building’s renovation.)
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, lunch and dinner.
In an environment of casual elegance,
we give diners the perfect place to enjoy a meal at their leisure in the company of friends, fellow diners and our attentive staff.
At times we even offer entertainment to complement the cuisine.
Keep an eye out for talented musicians with local flavor who will help enhance your experience at Sir Winston.
For those who prefer lighter fare and spirited conversation,
our wine loft is the right destination, with its amazing selection of local and national wines and a selection of delicious appetizers from our small plates menu.
Digby Stridiron, Executive Chef
Our name may be old and familiar, but what we bring to the city is new and unique.
We like to say we have two kinds of customers – those who remember eating at Sir Winston, and those who soon will.