Sir Winston Wine Loft & Restaurant is a polished downtown restaurant and wine destination at 104 W 4th St, Winston-Salem, NC 27101, in the city’s central Fourth Street district. Its name recalls the original Sir Winston, a beloved gathering place that occupied this Pepper Building location from 1967 through the 1990s; today, travelers come for a composed meal, a broad wine selection, and the slower pace of the Wine Loft.
What to Expect at Sir Winston Wine Loft & Restaurant
The present-day restaurant deliberately carries forward the social role of its predecessor while setting a more contemporary tone: elegant without formality, comfortable for a solo glass of wine yet polished enough for client lunches and anniversary dinners. The main restaurant and its separate Wine Loft make this more than a quick downtown stop. Plan to settle in, order wine with your meal, and treat the visit as an evening rather than a pre-show rush.
Wine is the organizing idea here. The list draws from multiple global wine regions, giving diners a useful reason to ask the staff for a pairing rather than defaulting to a single familiar bottle. Check the official menu before arrival for current food and wine offerings, as selections can change. The setting also has local weight: this is the revived Sir Winston in the former Pepper Building, linking a current dining room to a downtown address long associated with Winston-Salem hospitality.
- Wine Loft: A dedicated lounge-oriented space for lingering over wine, meeting friends, or having a quieter drink after downtown events.
- Revived local name: The restaurant honors the original Sir Winston, which occupied this address for more than two decades beginning in 1967.
- Global wine focus: The wine program is built around carefully selected bottles from wine regions around the world.
- Downtown Fourth Street address: Its central location suits lunch meetings, dinner before a performance, and an evening walk through the core.
- Private events: The restaurant offers private-event options; contact the team directly for group dining arrangements.
Sir Winston Wine Loft & Restaurant at a Glance
| Detail | Information |
|---|---|
| Address | 104 W 4th St, Winston-Salem, NC 27101 |
| Neighborhood / Area | Downtown Winston-Salem; West Fourth Street / Pepper Building area |
| Operating Hours | Mon–Thu & Sun 6:30am–11pm; Fri–Sat 6:30am–12am |
| Admission / Price Range | No admission; $$$ polished restaurant and wine-bar experience. See the official menu for current prices. |
| Recommended Visit Duration | 1.5 to 2.5 hours for dinner and wine; 45 to 75 minutes for a drink or lunch meeting |
| Nearest Transit / Parking | WSTA Downtown Transportation Center is about a 5-minute walk; use nearby downtown public parking garages or metered street spaces. |
| Official Website & Phone | sirwinstonrestaurant.com · +1 336-722-0795 |
Visiting Tips, Getting There & Nearby Pairings
Reserve ahead for Friday and Saturday dinner, particularly if your party wants the Wine Loft or is attending a nearby show. Weekday lunch and earlier dinner reservations are better choices for conversation and unhurried service. The restaurant is in the downtown grid, a short walk from the WSTA Downtown Transportation Center; drivers should allow time to find a space in a public garage or at a metered curb spot. Call ahead for private-event, large-party, and current seating questions.
The historic Pepper Building setting gives the restaurant its character, but guests needing step-free routing or wheelchair-specific seating should telephone before booking so the team can match the reservation to the appropriate entrance and room. Pair dinner with a walk through Winston Square Park, roughly 10 minutes away on foot, or an overnight at the Kimpton Cardinal Hotel, only about a block away. Fourth Street’s compact downtown restaurant and bar corridor also makes the Wine Loft a natural final stop after shopping, a performance, or an evening downtown.
Frequently Asked Questions
When is Sir Winston Wine Loft & Restaurant open, and when should I go?
It is listed as open 6:30am–11pm Monday through Thursday and Sunday, with Friday and Saturday hours extending to midnight. For dinner, book an earlier weekday table for the calmest pace; weekend evening reservations are prudent.
Does Sir Winston require tickets or reservations?
There is no admission charge. Reservations are recommended for dinner and are especially useful for weekends, celebrations, business meals, and groups; use the restaurant’s official website or call +1 336-722-0795 for current availability.
How long should I budget for a meal?
Allow 1.5 to 2.5 hours for a full dinner with wine, particularly if you want pairing guidance or time in the Wine Loft. A lunch meeting or a single glass and small bite can fit into roughly 45 to 75 minutes.
Is Sir Winston suitable for families and guests with mobility needs?
The restaurant’s polished but relaxed approach can work for families with older children who are comfortable with a longer meal, as well as couples and business diners. Because it occupies a historic downtown building and includes a separate loft space, call in advance to arrange step-free access and suitable seating.
When planning your Winston-Salem travel guide or browsing verified restaurants in Winston-Salem, pair this stop with standout local spots including Delta Arts Center, Historic Town of Salem, Firebirds Wood Fired Grill, and Hotel Indigo Winston-Salem Downtown, an IHG Hotel (nearby).
