It’s midweek in downtown Raleigh — the perfect time to unwind, grab a drink, and dive into live music, trivia, or creative workshops across the city. Whether you’re in the mood for smooth jazz, a round of music bingo, or karaoke that lasts till 2 a.m., this Downtown Raleigh After-Work Guide has your Wednesday plans covered.
🍷 Wine, Dine & Relax
Wine Wednesdays at Sitti Authentic Lebanese
📍 Sitti Authentic Lebanese, 137 S Wilmington St
🕚 11 AM – 10 PM
🍷 Half-off bottles of wine all day!
Spend your Wednesday at one of downtown Raleigh’s most beloved restaurants. Savor authentic Lebanese dishes — from fresh mezze to grilled lamb — while enjoying Sitti’s famous Wine Wednesday specials.
Live Music in the Bar at Vidrio
📍 Vidrio, 500 Glenwood Ave
🕕 6 PM – 10 PM
Unwind with small plates, craft cocktails, and live tunes in Vidrio’s gorgeous Mediterranean-style bar. The perfect post-work lounge spot for conversation and atmosphere.
🎶 Music Lovers’ Night Out
Live Jazz with Al Strong and Friends
📍 Boatman Spirits Co., 319 W Davie St
🕗 8 PM – Midnight
Celebrate Raleigh’s jazz scene with Grammy-recognized trumpeter Al Strong and his talented band. Smooth vibes, great cocktails, and pure downtown cool — a must-attend midweek music ritual.
Wednesday Karaoke at Neptunes Parlour
📍 Neptunes Parlour, 14 W Martin St
🕘 9 PM – 2 AM
Step underground for one of Raleigh’s most legendary karaoke nights. From classics to guilty pleasures, it’s your time to shine under the neon lights at Neptunes.
🧠 Trivia, Bingo & Midweek Games
Trivia at the Brewery
📍 Incendiary Brewing Taproom, 602 N Person St
🕖 7 PM – 9:30 PM
Bring your team and test your knowledge while sipping local craft beer. Free to play and prizes for winners — because Wednesdays were made for bragging rights.
Trivia Night at Longleaf Swine
📍 Longleaf Swine, 300 E Edenton St
🕖 7 PM – 8:30 PM
Join the BBQ and beer crowd at Longleaf Swine for another round of fun, fast-paced trivia. Grab some smoked wings, local brews, and show off your smarts.
Wednesday Night Music Bingo
📍 Wolfe & Porter, 210 S Wilmington St
🕖 7 PM – 10 PM
Bingo meets your favorite hits! Match songs instead of numbers while enjoying craft cocktails and good company.
✍️ Creative After-Work Workshops
Modern Calligraphy & Pumpkin Lettering for Beginners
📍 Wolfe & Porter
🕡 6:30 PM – 8:00 PM
Learn the art of brush lettering in a cozy creative setting. Perfect for beginners who want to master calligraphy with a seasonal twist — pumpkin lettering!
Sip & Script at Wolfe & Porter
📍 Wolfe & Porter
🕡 6:30 PM – 8:00 PM
A hands-on calligraphy workshop that pairs lettering instruction with sips of your favorite drink. It’s a relaxing, artsy way to spend your evening downtown.
🚴♂️ For the Active Crowd
Wednesday Night Ride at Crank Arm Brewing
📍 Crank Arm Brewing, Warehouse District
🕡 6:30 PM – 9:30 PM
Join Raleigh’s cycling community for the weekly Wednesday Night Ride. The route winds through downtown and ends right where it starts — with cold beers, community, and post-ride laughs.
🌙 Make It a Midweek to Remember
From Wine Wednesday and live jazz to karaoke till 2 a.m., downtown Raleigh is buzzing with ways to celebrate the middle of the week. Grab your friends, meet new ones, and make your Wednesday night something special.
📲 For more local events, guides, and Raleigh happenings, visit DoRaleigh.com — your source for everything happening in the heart of the city.
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