The Triangle Entertainment Guide – Monday, September 22, 2025

Looking for the best things to do around Raleigh, Durham, Chapel Hill, and beyond this Monday? From free chili and Oktoberfest celebrations to open mic nights, comedy shows, and family-friendly activities, the Triangle is buzzing with events. Here’s your guide to what’s happening today, September 22, 2025.

🌶️ Free Bowl of Chili at Wendy’s

All Day | FREE | Wendy’s (multiple locations)

Celebrate the first day of fall with a warm, free bowl of chili at participating Wendy’s restaurants across the Triangle.

🍻 Oktoberfest at Ponysaurus Brewing Co.

All Day | FREE | Ponysaurus Brewing Co., Raleigh

Raise a glass to autumn at Ponysaurus Brewing’s Oktoberfest celebration, complete with craft beer and community vibes.

👶 Total Tot Time – Free Play for Kids

10:00 a.m. – 12:00 p.m. | FREE | W.D. Hill Recreation Center, Durham

Bring little ones up to age 5 for free play fun in a safe and welcoming space.

📚 Leyendo con el Centro – Preschool Storytime

11:00 a.m. – 12:00 p.m. | FREE | Chapel Hill Public Library

A bilingual storytime for preschoolers, encouraging early literacy and cultural connection.

🍺 Mug Monday at Oaklyn Springs Brewery

4:00 p.m. – 7:00 p.m. | $5 | Oaklyn Springs Brewery, Fuquay-Varina

Enjoy $5 20oz mugs of your favorite brews during this Monday special.

🍗 Durham Beer Garden Wing Night

5:00 p.m. – 10:00 p.m. | $0.75 per wing | Durham Beer Garden

Grab 75¢ wings (dine-in only) and enjoy one of Durham’s best Monday deals.

🎤 Open Mic Night at Steel String Brewery

6:00 p.m. – 11:00 p.m. | FREE | Carrboro

Support local talent or hop on stage yourself at this lively open mic session.

🏈 Flag Football Skills for Girls

6:15 p.m. – 7:15 p.m. | $6–$11 (series) | W.D. Hill Recreation Center, Durham

A skills-building program for girls to sharpen their game while having fun.

🌌 Fall Equinox Labyrinth Walk

6:30 p.m. – 7:00 p.m. | FREE | St. Paul’s Episcopal Church, Smithfield

Celebrate the equinox with a reflective labyrinth walk in a serene setting.

🥏 Disc Golf Putting League at The Glass Jug

6:30 p.m. – 9:00 p.m. | FREE | RTP

Practice your short game with friends and fellow disc golf enthusiasts.

😂 Cosmic Chuckles: Weekly Comedy Show

7:00 p.m. – 9:00 p.m. | FREE | Flying Saucer, Raleigh

Get your laughs in with this free weekly comedy series hosted at Flying Saucer.

🎨 Adult Coloring Night at KōMANA Brewing Co.

7:00 p.m. – 9:00 p.m. | FREE | Cary

Unwind and get creative at this relaxed adult coloring social.

🎲 Board Game Night at Moon Dog Meadery

7:00 p.m. – 11:00 p.m. | FREE | Durham

Sip mead, meet new people, and play classic and modern board games.

🎶 Carrboro Open Mic at Speakeasy

8:00 p.m. – 11:59 p.m. | FREE | Carrboro

Cap off the night with live performances and community vibes at Speakeasy’s open mic

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

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