Weekender: 23+ Events in Winston-Salem this Weekend, including Kentucky Derby Watch Parties, Spring Folly, and Blooms in the Atrium

Making weekend plans? Check out these 23+ events in Winston-Salem this weekend (April 30 – May 3), including Spring Folly, Kentucky Derby watch parties, and Blooms in the Atrium!

Don’t forget to look at our live music guide — it’s updated weekly.

Thursday, April 30

• Wine Women & Shoes – Sip, shop, and savor an evening out at Legacy Stables & Events! Proceeds benefit Ronald McDonald House Charities of the Piedmont Triad. 5:30 PM
• Blooms in the Atrium – Create a custom floral arrangement with a local florist at 500 West 5th! 6 PM
• Mahjong 102 – Already know the basics? Join Camel City Mahjong at Peacehaven Chick-fil-A to review and solidify your game knowledge. 9:30 AM
• Baseball – Cheer on the Dash as they take on the Greensboro Grasshoppers! Daily games through Sunday. Theme highlights: Tobacco Beetles rebrand and Star Wars Day.

Friday, May 1

• Johnny Loves Johann – Bach, reimagined. Experience the music of Bach performed by a GRAMMY-winning violinist alongside a breathtaking dance performance at Agnes de Mille Theatre. Performances available through Sunday.
• Derby Bunco Night – Play Bunco and compete for the best derby hat at the Historic Broyhill! Proceeds benefit the Fostering Faith Foundation. 6 PM
• Spring Folly – Shop from local vendors, listen to live music, and explore downtown Kernersville during one of its biggest events of the year! Runs through Sunday.
• Open House – Enjoy free bites, mocktails, bakery treats, and a shopping experience at Short Street Bakehouse! Did we mention there are also prizes? 5-8 PM
• Pink Out at the Races – Watch horse races and sip on mint juleps at Dram & Draught! Proceeds from their specialty menu benefit the Pretty In Pink Foundation. Runs through Saturday.
• Wine Tasting – Sip on a flight paired with charcuterie, enjoy an educational tasting session, and play trivia at the Delta Arts Center! 6 PM
• Plant Sale – Your garden could use another plant. Shop for native plants, perennials, annuals, and more at The Arboretum at Tanglewood Park! 8 AM – 2 PM

Saturday, May 2

• Wise Man Derby – Watch the Kentucky Derby, shop a vintage market, and listen to live music (including a Grateful Dead cover band) at Wise Man Brewing. All-day event.
• Anniversary – Celebrate 1 year of Pure Sweat Sauna Studio with a free wellness expo, complimentary infrared sauna and cold plunge sessions, and a vendor market! Registration required. 2-6 PM
• Comedy Night – The lineup and venue? Top secret. Don’t Tell Comedy emails you the location the morning of the show! 8:15 PM
• Brookstown Block Party – Browse art vendors and grab a bite from food trucks at Cotton Street Apparel! 12-5 PM
• Free Tennis – Ace! Sign up for free child and adult clinics with Triad Tennis at Forsyth Country Day School. Sessions from 9 AM – 1 PM.
• Women’s Legacy Parade – Celebrate the incredible women in your life at Corpening Plaza! Watch the parade, groove to live music, and grab a bite from local food trucks. Parade at 1 PM; festival runs until 5 PM.
• Community Day – Face painting, scavenger hunts, disc golf tournaments, and more — don’t miss Lewisville’s first-ever community day! Free breakfast and lunch included. 10 AM – 2 PM
• Petals & Pints – Cross off your Mother’s Day shopping list. Browse 15+ vendors and grab a plate of BBQ at Radar Brewing! 1-6 PM
• The Wizard of Oz – Watch the classic movie at Tanglewood Park for free; arrive early for a Dash City Saxophone Quartet performance! Movie starts at sundown.
• Spring Market – Shop homemade items at Winston Junction Market. Live music and food trucks onsite! 11 AM – 4 PM

Sunday, May 3

• Rescue for the Roses – This Derby-themed fundraiser at Medaloni Cellars features Uptown Dueling Pianos, a silent auction, and lawn games! Proceeds support Red Feather Equine Sanctuary. 12 PM
• Trade Street Farmers Market – Taste the difference. Support your local producers by shopping fresh fruit and veggies, baked goods, and more on Trade Street! 10 AM – 2 PM
• May Day Festival – Celebrate spring with face painting, flower crowns, live music, and a vendor market at Brouwerij DuBois! 12-8 PM
• Line Dance Party – Pick up a new routine with Maggie Shipley, then hit the floor for open dancing! 12:30-4:30 PM
• Embroidery 101 – Learn the basics of embroidery and stitch a dandelion at Village Fabric Shop! Supplies included. 4 PM