Downtown Raleigh comes alive this Wednesday night with smooth jazz, karaoke, trivia, and local brews. Whether you’re looking to sing your heart out, unwind with a glass of wine, or enjoy live music and community vibes, there’s something for everyone in the heart of the capital city. Here’s your full entertainment lineup for Wednesday, October 8, 2025.

🍷 Wine Wednesdays at Sitti Authentic Lebanese

🕚 11:00 a.m. – 10:00 p.m. | 📍 Sitti, Downtown Raleigh

Enjoy a midweek escape with half-priced bottles and glasses of wine at one of Raleigh’s most beloved Mediterranean restaurants. Perfect for a romantic dinner or a relaxed evening with friends.

🧙‍♂️ Dungeons n’ Drafts @ Crank Arm Brewing

🕡 6:30 p.m. – 10:00 p.m. | 📍 Crank Arm Brewing, Warehouse District

Grab your dice and your favorite pint for an evening of adventure and craft beer. Whether you’re a seasoned Dungeon Master or just curious, this event is all about creativity, camaraderie, and fun.

🎷 Live Jazz with Al Strong & Friends

🕗 8:00 p.m. – Midnight | 📍 Boatman Spirits Co.

Unwind midweek with live jazz led by renowned trumpeter Al Strong and his talented ensemble. Smooth sounds, handcrafted cocktails, and a classy downtown vibe make this a must for Raleigh music lovers.

🎸 Live Music in the Bar + Wednesday Night Live at Vidrio

🕕 6:00 p.m. – 10:00 p.m. | 📍 Vidrio, Glenwood South

Vidrio’s vibrant bar transforms into a live music lounge every Wednesday evening. Sip craft cocktails, enjoy Mediterranean-inspired bites, and groove to live tunes all night long.

🎤 Wednesday Karaoke at Neptunes Parlour

🕘 9:00 p.m. – 2:00 a.m. | 📍 Neptunes Parlour, Fayetteville Street

Step into the spotlight at one of Raleigh’s most iconic underground venues. Whether you’re a karaoke pro or just singing for fun, Neptunes brings the energy, crowd, and good vibes every Wednesday night.

🧠 Trivia Night at Longleaf Swine

🕖 7:00 p.m. – 8:30 p.m. | 📍 Longleaf Swine, Person Street

BBQ, beer, and brainpower! Gather your crew for an evening of trivia and tasty eats in this beloved Raleigh smokehouse.

🎵 Wednesday Night Music Bingo at Wolfe & Porter

🕖 7:00 p.m. – 10:00 p.m. | 📍 Wolfe & Porter, Downtown Raleigh

It’s bingo with a musical twist! Listen, mark your cards, and win prizes while enjoying drinks and downtown’s lively bar scene.

Plan Your Perfect Downtown Wednesday

Raleigh’s nightlife scene offers the perfect midweek mix of music, fun, and flavor. Whether you’re exploring Fayetteville Street, Glenwood South, or the Warehouse District, there’s no better time to experience the city’s creative pulse.

Your week, your city, your fun — stay connected with everything happening in the Raleigh at DoRaleigh.com