The Downtown Raleigh Entertainment Guide Wednesday October 15th Edition

Downtown Raleigh is buzzing this Wednesday night with music, laughter, creativity, and good vibes from sunup to last call. Whether you’re looking to sip fine wine, belt out karaoke classics, or unwind with live jazz, there’s no shortage of things to do in the heart of the city.

Start your afternoon with a glass (or two) at Wine Wednesdays at Sitti Authentic Lebanese, running from 11 a.m. to 10 p.m. Treat yourself to Sitti’s curated wine list paired with Mediterranean flavors in a relaxed downtown setting — perfect for a midweek wind-down.

If you’re in the mood for a creative night out, head to Wye Hill Kitchen & Brewing for Modern Calligraphy & Pumpkin Lettering for Beginners from 7 to 8:30 p.m. Enjoy hands-on fall fun while overlooking Raleigh’s skyline with a pint of local brew in hand.

Music lovers have plenty to choose from this evening. Vidrio brings the ambiance with Live Music in the Bar from 6 to 10 p.m., followed by Wednesday Night Live Music from 7 to 10 p.m. Nearby, Boatman Spirits Co. keeps things smooth with Live Jazz featuring Al Strong and Friends from 8 p.m. to midnight — a can’t-miss experience for jazz enthusiasts and cocktail lovers alike.

Feeling lucky? Test your knowledge at Trivia Night at Longleaf Swine from 7 to 8:30 p.m., or join the crowd at Wolfe & Porter for Wednesday Night Music Bingo from 7 to 10 p.m. Both are perfect for groups, with great food, drinks, and lively energy.

For those craving laughs, the Oak City Comedy Festival presents Laugh & Lounge Longleaf at 8 p.m. inside the Longleaf Hotel — showcasing local comedians and a fun, relaxed atmosphere that keeps the midweek mood light.

And if you still have energy left after all that, end the night at Neptunes Parlour for Wednesday Karaoke, running from 9 p.m. to 2 a.m. Belt your favorite songs underground at one of Raleigh’s most iconic nightlife spots.

From music to comedy, wine to karaoke, Wednesday in Downtown Raleigh proves the city never slows down. Your week, your city, your fun — stay connected with everything happening in the Raleigh at DoRaleigh.com

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The Downtown Raleigh Entertainment Guide Wednesday October 8th Edition

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

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