Weekender: 24+ Events in Winston-Salem this Weekend Including Wine Dinner, Volleyball Tournament, and Vintage Market!

Making weekend plans? Enjoy a wine-paired dinner at The Downtown Grille, watch (or join in) the YMCA volleyball tournament, or shop at the Winston Vintage Market!

Check out these 24+ events in Winston-Salem this weekend, and don’t forget to also look at our live music guide!

May 29, 2024

Thursday, May 30

• Wine Dinner – Enjoy a four-course, wine-paired dinner at The Downtown Grille, featuring wine from Biltmore Winery. 6 PM
• Tequila Tasting – Try five different tequilas and learn how to make two tequila-based cocktails at The Playground Golf & Sports Bar. 6:30 PM
• R&B and Poetry – Enjoy live performances of R&B and spoken word at Bar Nola, with rounds of music bingo and poetry karaoke thrown in the mix! 8-11 PM
• Baseball Games – The Winston-Salem Dash faces the Hickory Crawdads at Truist Stadium! This week, theme nights include Margaritaville Night and Strikeout Cancer Day. Games every night through Sunday starting at 7 PM.

Friday, May 31

• Outdoor Movie – Join Senior Services at the Intergenerational Center to watch Jumanji: Welcome to the Jungle. Come early for a performance from the Triad Swing Band! Band plays at 7 PM, movie starts at 8:15 PM.
• Salsa Dance – Head to the Coal Pit for a beginner salsa or bachata class, followed by social dancing with a live DJ. 7-11 PM
• Comedy and Brewpub Tour – Climb aboard the “jolly trolley” for a hilarious trip around town featuring an onboard comedy show and a tasting at a local brewpub. 7 PM
• House Hangs – Hang out at SECCA and enjoy a live DJ, conversation, cocktails, and dinner prepared by Native Root and MO’ Empanadas. 5-8 PM
• Reopening – The Humble Bee Shoppe is reopening! The dessert shop offers 20+ flavors of macaroons, cupcakes, dream tarts, and more. 12-4 PM

Saturday, June 1

• BASH Volleyball Tournament – Gather a team for the tournament at the Jerry Long Family YMCA! Triples play on Saturday and reverse coed doubles play on Sunday.
• Green Home Tour – Piedmont Federal Bank is proud to sponsor the Triad’s first Green Home Tour. Tour eight homes in Winston-Salem for a firsthand look at innovative and exciting green home trends in action. 11 AM – 2 PM
• New Restaurant – Try Jade Express’ famous bourbon chicken at its grand opening! The new Chinese/hibachi restaurant is located at 1103 Salis Creek Pkwy.
• Brunch Run – Run in Piedmont Forest School’s first annual 5K at The Quarry at Grant Park! Enjoy pancakes, nature crafts, and live music in support of the school’s Growing Together Fund. 9 AM – 1 PM
• Taco Festival – Head to the Winston-Salem Fairgrounds for tacos, live DJs, local shopping, and a fun zone with axe throwing + corn hole! 12-5 PM
• Pride Cookout – Enjoy grilled food and a live DJ at South Fork Park for the first day of Pride Month. 4-8 PM
• Supper Club – Unwind at Simply Sonya’s with great food, Southern soul music, and a performance by comedian Burpie! 8:30 PM
• Summer Shindig – Welcome in summer at the Jerry Long Family YMCA with a live concert featuring UNKNOWN ARTIST, a kids zone, and food trucks. 5-8 PM
• Chase the Dream 5K – Get ready for this glow-in-the-dark 5K at Bailey Park, supporting the Dream Center. 8 PM
• Street Festival – Food trucks, 75 vendors, live music, a kids zone, and more – experience it all at Depot Street in Mocksville. 11 AM – 7 PM
• Hard Hat Tour – Take a tour of the former Coca-Cola Bottling Plant! The building’s owner will share its history and the plans to transform the plant into a restaurant and event space. 9-11 AM
• Winston Vintage Market – Find clothing from the 70s, 80s, 90s, and 00s from 20+ vendors at ALV Nightclub. Most vendors’ price points start at just five dollars! 11 AM – 5 PM
• Mario Kart Tournament – Start your engines! ROAR hosts a Mario Kart 8 tournament in its gaming space, The BUNKR, complete with a UNSCA 4-piece band performing music from the iconic soundtrack. 5-11:30 PM
• Flamenco Night – The Raleigh-based Eduardo de Rosamaria Flamenco Ensemble performs at Pink Moon Cafe. 9-11 PM
• Grand Opening – Performance Nutrition, a veteran-owned supplement store, celebrates its grand opening with giveaways and prizes at 2253 Cloverdale Ave. 2-5 PM

Sunday, June 2

• Farmers Market – Find fresh produce, fruit, beer, and even knife sharpening at Foothills Tasting Room. 12 PM
• Funky Llama Market – Divine Llama Vineyards hosts an art, craft, and vintage market. Shop for unique items and don’t forget to say hi to the llamas! 1-5 PM
• Wine For Woofs – Taste 10 wines, enjoy a slice from Uptown Pizza, and meet foster pups at Meladoni Cellars. A percentage of proceeds from the event benefit the Animal Adoption and Rescue Foundation (AARF). 1-3 PM

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