Winston-Salem's Cigar Scene
Winston-Salem is the historic tobacco capital of America, the city where R.J. Reynolds built an empire that defined an industry. The towering Reynolds Building downtown, which inspired the design of the Empire State Building, still stands as a monument to the leaf that built this city. Walking the streets of Winston-Salem, you can feel the tobacco heritage in the old warehouse districts, the preserved factory buildings, and the deep local knowledge of fine tobacco that persists to this day.
Today's Winston-Salem cigar scene honors that legacy while forging its own identity. Top Leaf Cigar Lounge anchors the downtown scene with rare boutique blends you will not find elsewhere, while established shops like Robinhood Tobacco and The Pipe and Pint carry on decades of tobacco retail tradition. The Piedmont Triad region surrounding the city adds even more options, making Winston-Salem a true pilgrimage destination for anyone who appreciates the craft and history of premium tobacco.
Cigar Lounges (8)
These establishments feature dedicated smoking lounges where you can relax and enjoy your cigars in comfortable, well-ventilated spaces.
Top Leaf Cigar Lounge
The anchor of Winston-Salem's cigar scene, boasting what many consider the best cigar selection in North Carolina. Over 300 cigars to choose from including rare boutique blends from Felix Assouline, Black Label Trading Company, MBombay, and Hiram & Solomon. Features a fully attended bar with craft beer and spirits, comfortable indoor and outdoor seating, a semi-private room, and multiple TVs. Ages 21 and up only.
The Pipe and Pint
A well-established tobacco shop serving the Winston-Salem community with a focus on both cigars and pipe tobacco. The walk-in humidor features premium brands and the knowledgeable staff can guide newcomers and seasoned smokers alike. Open Monday through Saturday, this is the kind of straightforward, no-frills tobacco shop that tobacco country does best.
Robinhood Tobacco
A Winston-Salem institution since 1998, Robinhood Tobacco features a well-maintained walk-in humidor with a wide variety of premium cigars. Carries major brands like Arturo Fuente, Romeo y Julieta, and La Gloria Cubana alongside boutique lines including AJ Fernandez, Olivia, Nub, La Flor Dominicana, Java, and Acid. Open seven days a week with convenient hours.
Smokey Shay's
Located on the eclectic Burke Street in the Buena Vista neighborhood, Smokey Shay's carries a selection of humidor cigars alongside pipes, tobacco, and accessories. The bohemian Burke Street setting, lined with independent shops and restaurants, makes for a great afternoon of browsing. Multiple locations across the Piedmont Triad region.
Blue Ridge Tobacco
A friendly neighborhood tobacco shop established in 1999 on Cloverdale Avenue in the Ardmore area. Features a walk-in cigar humidor kept at precise humidity levels, ensuring every cigar is in peak condition. Carries a broad selection from everyday smokes to premium hand-rolled options. Open early mornings through evenings for maximum convenience.
Tobacco Shop & Cigars
A long-standing tobacco shop on Silas Creek Parkway serving the south side of Winston-Salem. Known for competitive pricing and a solid selection of cigars, pipe tobacco, and accessories. The no-frills approach appeals to regular smokers who know what they want and appreciate straightforward service at fair prices. Open daily from early morning.
Havana Phil's Cigar Company
A Davidoff Appointed Merchant just 30 minutes from Winston-Salem in nearby Greensboro, making it an essential stop for Piedmont Triad cigar lovers. State-of-the-art Spanish cedar walk-in humidors house an extensive inventory including Davidoff, Rocky Patel, Arturo Fuente, and many boutique brands. The exclusive Davidoff Lounge opens Tuesday through Saturday evenings for a premium experience.
The Smoke and Oak
A bourbon and cigar bar in nearby Lexington, about 25 minutes south of Winston-Salem. Features a carefully curated cigar humidor alongside an impressive bourbon and cocktail menu. The warm, inviting atmosphere is perfect for relaxing with friends over a smoke and a well-crafted drink. Open Tuesday through Sunday with Sunday hours for a leisurely afternoon session.
Winston-Salem Cigar Tips
Best Times to Visit
Weekday afternoons are perfect for a relaxed session at shops like Robinhood Tobacco or The Pipe and Pint. Friday and Saturday evenings bring the energy at Top Leaf and downtown cocktail spots. Many tobacco shops open early, by 8 or 9 AM.
Neighborhoods to Explore
Downtown/West End is home to Top Leaf and the historic Reynolds Building. Robinhood Road offers classic tobacco shopping. Burke Street in the Buena Vista neighborhood has a bohemian vibe. Nearby Greensboro and Lexington add regional depth.
What to Try
Smoke a rare boutique blend at Top Leaf Cigar Lounge with a local craft beer. Browse the deep humidor at Robinhood Tobacco for AJ Fernandez and La Flor Dominicana sticks. Make the short drive to Havana Phil's in Greensboro for Davidoff exclusives.