Pick any bottle from JOLO’s lineup, and chances are it boasts a string of 15-plus awards. Not just any awards—think Best in Show and Best of Class from prestigious competitions like the Los Angeles Invitational Wine & Spirits Challenge and the International Eastern Wine Competition. But it’s not just the wines racking up accolades. This year, OpenTable named End Posts Restaurant one of the Top 100 Most Romantic Restaurants in America. Last year, it made OpenTable’s Top 100 Brunch Spots in America and was crowned North Carolina’s Most Beautiful Restaurant by the Love Food Awards. To top it off, JOLO took home Best Winery/Vineyard in The Go-To Winston-Salem’s 2025 Reader’s Choice Awards.

Good to Know: Reservations are required, and the venue is strictly 21 and over.

Don’t let the laid-back atmosphere at Haze Gray fool you—Deane and Becky Muhlenberg are serious about their wine. In 2024, they took home silver and bronze medals at both the American Wine Society Competition and the NC Wine Competition. As you sip, take a stroll down to the pasture to watch the cows and horses graze, or simply relax on the back deck and soak in the peaceful countryside views.

Since opening in 2004, Childress Vineyards’ winemaker, Mark Friszolowski, has amassed an impressive 750-plus awards. Two of his wines have earned spots on the 50 Best Wines of the World list, and the winery has been honored with the prestigious Governor’s Cup Award five times. 

The accolades don’t stop there—Wine Enthusiast Magazine named its tasting room one of the Top 25 Tasting Rooms in America, while its on-site restaurant, The Bistro, secured a spot on OpenTable’s Top 100 Scenic Restaurants in America. Whether you’re here for a tasting or a full dining experience, Childress Vineyards delivers excellence on both fronts.

Good to know: During the warmer months, cool down with their Insta-famous wine slushies!

Owned by the same family as JOLO, it is no surprise that Rayson is already making a name for itself in the world of wine. They have quickly racked up medals at prestigious competitions like America’s Wine Cup, the American Wine Society Competition, the NC Fine Wines Competition, and the Southeast Regional Winemaker Challenge—earning multiple platinum, gold, and Best in Show honors. Their restaurant, Bistro Europa, is also gaining recognition, securing a spot on OpenTable’s Top Ten for Value in Winston-Salem list. 

Good to Know: Reservations are required and the venue is strictly 21 and over.

Raffaldini Vineyards has earned numerous accolades over the years, with recent honors from esteemed wine critic James Suckling, the International Wine & Spirits Competition, and the International "East Meets West" Wine Challenge. It was also named one of The South’s Best Vineyards by Southern Living Magazine, solidifying its reputation as a top-tier destination for wine lovers. 

Beyond its award-winning wines, Raffaldini stands out for its commitment to the environment by earning recognition from the National Wildlife Federation as a Certified Wildlife Habitat for its efforts to enhance and preserve the local ecosystem. 

Good to Know: This venue is strictly 21 and over.

Patrick and Wendy McNabb wasted no time making their mark after taking over Carolina Heritage. In 2024, their wines earned two gold, four silver, and two bronze medals at America’s Wine Cup, with winners including The O.G. Blend, Daredevil, and their signature selections—Glogg and Apple Pie. It’s not just their wines bringing home awards, but their innovative packaging is turning heads too. 

With glass recycling no longer available in the county, Carolina Heritage made the bold move to switch to paper bottles. Their Apple Pie bottle and label design won Gold at the Southeast Regional Winemaker Challenge, proving their commitment to both sustainability and creativity.

Known for their bold reds, Piccione was recently recognized in Forbes Magazine for having some of the best Italian varietal red wines in The San Francisco International Wine Competition. In addition, they received awards from the Finger Lakes International Wine Competition and Mid-Atlantic Southeastern Wine Competition. 

Wine Enthusiast Magazine has featured them in their guide to under-the-radar wineries in North Carolina, and Piccione came out on top in the Drink category of the Made in NC Awards hosted by Our State Magazine. The mountain views from their new tasting room are sure to leave you breathless and their quality wines will keep you coming back.

Good to know: On Fridays, food trucks can be found on site and all glasses of wine are $8!

Learn more about more things to do in Winston-Salem and places to stay while exploring these award-winning wineries by downloading or requesting a Visitor Guide and signing up for our e-newsletter.