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The Triangle Event Guide – Things to Do Monday, December 29th Edition

Looking for things to do across the Triangle on Monday, December 29, 2025? From free community celebrations and holiday light displays to live music, comedy, game nights, and cultural events, the Triangle is packed with options to close out the year.

This Triangle Event Guide highlights events happening in Raleigh, Durham, Cary, Carrboro, and beyond—perfect for families, friends, and anyone looking to make the most of a Monday.

🎉 Monday, December 29, 2025 — Triangle Events

Cheapskate Day at Skate the Square

🕒 All Day | Discounted ($3 off)

📍 Fenton, Cary

Enjoy discounted skating all day at Fenton’s outdoor rink. Check the website for updated hours and availability.

Little WORLD Charity Holiday Model Train Show

🕙 10:00 am – 12:30 pm | FREE

🕜 1:30 pm – 5:00 pm | FREE

📍 Durham County Main Library

A family-friendly favorite featuring intricate model train displays while supporting a charitable cause.

Town of Cary’s Annual Kwanzaa Celebration

🕜 1:30 pm – 6:00 pm | FREE

📍 Cary Arts Center

Celebrate culture, heritage, and community with performances and reflections honoring the principles of Kwanzaa.

Monday Night NFL Football Watch Party

🕒 3:00 pm – 7:00 pm | FREE

📍 Crank Arm Brewing Company

Catch Monday Night Football with fellow fans in a relaxed brewery setting.

Illuminate Art Walk

🕟 4:45 pm | FREE

📍 Downtown Raleigh

Explore public art, illuminated installations, and creative spaces throughout downtown Raleigh on this guided art walk.

Durham Beer Garden: 75¢ Wings

🕔 5:00 pm – 10:00 pm | $0.75 wings (dine-in only)

📍 Durham Beer Garden

An affordable way to kick off the evening with food and drinks in downtown Durham.

🎄 Holiday Lights & Seasonal Favorites

Piper Lights

🕠 5:30 pm – 9:00 pm | FREE

📍 Piper Lights, Wake Forest

A must-see neighborhood holiday light display perfect for families.

Contentnea Fire Department Christmas Light Display

🕠 5:30 pm – 9:00 pm | FREE

📍 Contentnea Fire Department, Wilson

A festive drive-through display supporting local firefighters and holiday cheer.

Lake Myra Christmas Lights

🕠 5:30 pm – 10:00 pm | FREE

📍 Lake Myra, Wendell

One of the Triangle area’s most popular holiday light traditions.

North Carolina Chinese Lantern Festival

🕕 6:00 pm – 10:00 pm | $16.74–$30.64

📍 Koka Booth Amphitheatre

Walk through stunning illuminated lantern displays celebrating art, culture, and craftsmanship.

🎤 Nightlife, Comedy & Game Nights

Open Mic Night

🕕 6:00 pm – 11:00 pm | FREE

📍 Steel String Brewery, Carrboro

Local musicians, poets, and performers take the stage.

Early Karaoke

🕕 6:00 pm | FREE

📍 The Northside District

Start karaoke early and sing your favorites.

Cosmic Chuckles: Weekly Comedy Show

🕖 7:00 pm – 9:00 pm | FREE

📍 Flying Saucer, Raleigh

A weekly stand-up comedy showcase featuring local talent.

Adult Coloring Night

🕖 7:00 pm – 9:00 pm | FREE

📍 KōMANA Brewing Company, Cary

Relax, color, and unwind with a creative crowd.

Game Night

🕖 7:00 pm – 10:00 pm | FREE

📍 Crank Arm Brewing Company, Raleigh

Board games, cards, and casual competition.

Board Game Night

🕖 7:00 pm – 11:00 pm | FREE

📍 Moon Dog Meadery & Bottle Shop, Durham

Bring friends or meet new ones over classic and modern board games.

Air Hockey Tournament

🕗 8:00 pm – 10:00 pm | FREE

📍 Boxcar Bar + Arcade, Raleigh

Fast-paced fun with prizes and bragging rights on the line.

Carrboro Open Mic at Speakeasy

🕗 8:00 pm – 11:59 pm | FREE

📍 Speakeasy, Carrboro

A late-night open mic featuring music, poetry, and performance.

Make the Most of Your Monday in the Triangle

From cultural celebrations and holiday lights to comedy, karaoke, and game nights, Monday, December 29, 2025 is packed with things to do across the Triangle. Many events are free or low-cost, making it easy to explore multiple spots in one night.

Follow DoRaleigh.com for daily updates on government meetings, local festivals, and community happenings — your one-stop guide to everything Raleigh!

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The Downtown Raleigh After-Work Event Guide Thursday December 18th Edition

Looking for the best things to do after work in Downtown Raleigh? From happy hour drink specials and free wings to live music, improv, art walks, karaoke, and holiday pop-ups, Thursday, December 18 is packed with ways to unwind, connect, and celebrate the season downtown. Here’s your complete after-work event guide.

🍸 Happy Hour, Drinks & Social Meetups

Start the evening with drink specials and social vibes at some of downtown Raleigh’s favorite spots.

$10 Classic Cocktails All Day | Boatman Spirits Co. Enjoy expertly crafted classic cocktails at a special all-day price every Thursday. Singles Mingle 6:00–8:00 p.m. | Good Day Good Night Mix, mingle, and meet new people in a relaxed after-work social setting.

🎨 Arts, Creativity & Holiday Pop-Ups

Add some creativity and seasonal fun to your Thursday night.

Wrap It Up – Pop-Up Gift Wrapping 4:00–6:00 p.m. | Platform Get your holiday gifts professionally wrapped while supporting a downtown pop-up experience. Illuminate Art Walk Sip n’ Stroll Tour 5:45–6:45 p.m. | Raleigh Walking Tours Explore Downtown Raleigh’s Illuminate Art Walk with a guided sip-and-stroll tour featuring public art and holiday vibes. Pottery Painting Pop-Up: Holiday Edition 6:00–7:30 p.m. | Incendiary Brewing Taproom Sip craft beer while painting pottery in this festive, hands-on creative experience.

🎭 Comedy, Improv & Live Entertainment

Leela Improv Theatre: Drop-In Improv Class 7:00–9:00 p.m. | Leela Improv Theatre Jump into improv—no experience required—at this fun, interactive drop-in class. Frog Machine & Vitamin D (Live Music) 9:00–11:00 p.m. | Slim’s Downtown Catch live music late into the evening at one of downtown’s most iconic venues.

🏈 Sports, Wings & Late-Night Karaoke

Free Gussie’s Wings & Thursday Football 8:15 p.m. | Wolfe & Porter Watch Thursday Night Football and enjoy free wings while supplies last. Thursday Night Music Karaoke 8:00 p.m. | Wolfe & Porter Warm up your vocals and sing along to your favorite hits. Zenith Raleigh Downtown Karaoke 9:00 p.m. | Zenith Raleigh Keep the party going with late-night karaoke downtown.

Make the Most of Your Downtown Raleigh Evening

Whether you’re heading out straight from work or meeting friends later in the night, Downtown Raleigh offers something for everyone—from creative workshops and guided art walks to live music, football, and karaoke.

Check back daily on DoRaleigh.com for the latest after-work guides, weekend previews, and downtown happenings.

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