Flavortown Bound: Winston-Salem Eateries That Deserve a Spot on Diners, Drive-Ins, and Dives

Hey, food fans! Buckle up because Winston-Salem, North Carolina, is rolling out some seriously tasty eats that would make Guy Fieri’s taste buds do the cha-cha. This city’s got a flavor-packed lineup of spots screaming for a visit from “Diners, Drive-Ins, and Dives.” Ready to dive in? Let’s hit the road and check out these five Winston-Salem eateries that are Flavortown-approved!

Bobby Boy Bakeshop

1100 Reynolda Rd, Winston-Salem, NC 27104

As soon as you walk into Bobby Boy Bakeshop, you’re greeted by the irresistible aroma of freshly baked bread and sugary confections. Bobby Boy Bakeshop is run by the dynamic husband-and-wife duo John and Lucia Bobby. Recently, the bakery earned a spot as a semifinalist for the 2024 James Beard Award, recognized in the Outstanding Bakery category. What sets this bakery apart is its unwavering dedication to using only the finest ingredients. They source from local farms and use premium flours and butter, putting quality above all else. John also nurtures the bakery’s onsite garden, growing mint, basil, and edible flowers that find their way into the delicious recipes. They craft everything daily, from flaky croissants and sourdough loaves to seasonal tarts and indulgent éclairs. We think this is a bakery that Guy Fieri would totally flip for.

Cibo Trattoria

601 N Liberty St, Winston-Salem, NC 27101

For a taste of Italy that’ll make you want to do the mambo, Cibo Trattoria’s got you covered. Emerging from the legacy of Paul’s Fine Italian Dining, Cibo is led by the former chef, sous-chef, and longtime manager of Paul’s. At Cibo, you’ll find many cherished Italian dishes and Winston-Salem staples for over 30 years. Dig into their “Frutti Di Mare Al Cognac” (it is absolutely divine) or go classic with their “Capellini Prosciutto,” packed with rich flavors and comforting vibes. It’s like a trip to Italy without leaving Winston-Salem. Guy, listen up; Cibo Trattoria is a surefire ticket to Flavortown!

Heff’s Burger Club

285 W 4th St, Winston-Salem, NC 27101

Craving a burger that’s got some serious swagger? Head over to Heff’s Burger Club, where the patties are juicy, and the toppings are out of this world. Heff’s Burger Club’s smash burgers are taking the burger world by storm! If you have yet to try one, here’s the scoop: they use a 4 oz. patty that’s smashed thin for a quick cook that delivers a crispy, crunchy bite. Justin Webster, the executive chef and owner of Heff’s, describes them as “big, wide, and yummy.” “We believe they’re the ultimate burgers,” he says, and we couldn’t agree more. Justin Webster recently appeared on the Food Network show “Chopped.” Also, Heff’s Burger Club is a James Beard Best New Restaurant Semifinalist. The fun, laid-back vibe, and those crazy-good burgers are a Flavortown no-brainer!

Mission Pizza Napoletana

707 Trade St NW, Winston-Salem, NC 27101

Get ready for a pizza party like no other at Mission Pizza Napoletana (MPN)! These pizza maestros are all about that classic Neapolitan vibe, and their wood-fired oven is where the magic happens. Chef Peyton Smith is a James Beard Best Chef Southeast Semifinalist and the founder/owner/operator of MPN. Guy, this place is where authentic pizza dreams come true! While the Diavola and the Diego Marinara are the most popular pizzas, Smith also suggested a must-try pasta dish on the menu, the Bucatini All’Amatriciana.

Timmy’s Hot Chicken

237 W 5th St, Winston-Salem, NC 27101

Crank up the heat at Timmy’s Hot Chicken, where spicy is an understatement! This joint takes Nashville hot chicken to a whole new level with its fiery, flavorful offerings. The hot chicken is the star of the show here, and the chefs have nailed the perfect blend of heat and flavor to suit every taste. Whether you like it medium, hot, very hot, or hellfire, Timmy’s has the right level of spice for you. Each piece is expertly seasoned, battered, and fried to a golden crisp, delivering that crave-worthy crunch on the outside with tender, juicy meat on the inside. Guy, this spot is sure to add some serious heat to your culinary adventure!

Picture of Jeff Valentino
Jeff Valentino

Hi, it’s Jeff Valentino. In 2019 my 2 sons and I packed up and moved to Winston Salem from the suburbs of Chicago. We didn’t know one person here. I wished there was a resource for people like me who are considering a similar move, so I decided to make one!

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