Opinionation Trivia at House of Hops
2026-01-01 18:00 - 20:00, 2026-01-08 18:00 - 20:00 (America/New_York) | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops every Thursday, 6pm-8pm for Opinionation Trivia. This Family Fued-style trivia game is so much fun! Play at 6pm and again at 7pm for two chances to win $15 or $25 House of Hops gift cards. Bring the crew, bring food from neighbors Cafe Root Cellar or Mi Cancun, and enjoy!
More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Blues Jam at The MOD
2026-01-01 19:00 - 22:00, 2026-01-08 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Blues Jam hosted every Thursday, 7pm-10pm by Lo Taylor. This open jam is an excellent opportunity for those who share a love for the blues and wish to share their talents. Mr. Taylor and his band of talented musicians will make you feel right at home on our stage. Bring your voice, bring your instruments, or just bring your ears to partake in this musical delight. The Mod is dedicated to providing space for live music, great food, craft beverages, community, and love. Arrive early for musician sign-up or to grab a table for the evening. Any schedule changes due to weather, holidays, or unforeseen circumstances will be posted on their Facebook and Instagram pages.
See more events at The MOD.

Run and Roam Fridays at The Plant
2026-01-02 17:00 - 21:00, 2026-01-09 17:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country Inns Trail, with local beers from bmc brewing, wines and ciders from Starrlight, spirits from Fair Game, and sake from Koshu. Local dining available at Kingston 99 Kitchen and Ta Contento.
This free event takes place indoors and outdoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. See all events at The Plant.

Euchre Mondays at bmc
2026-01-05 18:00 - 20:00, 2026-01-12 18:00 - 20:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. No experience is needed. Monday is also $5 pint night at bmc brewing.
This event is free and takes place indoors. The space is wheelchair accessible. No pets are allowed. Free parking is available on-site. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Run Club at House of Hops
2026-01-06 18:00 - 20:00, 2026-01-13 18:00 - 20:00 | NC
Join House of Hops every Tuesday, 6pm-8pm for Run Club and 20%-off mixed six pack. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Piano Music at The Sycamore
2026-01-06 18:00 - 21:00, 2026-01-08 18:00 - 21:00, 2026-01-09 18:00 - 21:00, 2026-01-10 18:00 - 21:00, 2026-01-13 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Tuesday, Thursday, Friday, and Saturday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Live Piano Music. The series features a rotating list of local musicians. Past and present musicians include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here.
See more events at The Sycamore at Chatham Mills.

Music Bingo at Hops and Berry
2026-01-06 19:00 - 21:00, 2026-01-13 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come to Hops and Berry-Pittsboro for Music Bingo every Tuesday, 7pm-9pm. This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Pub Trivia at Doherty's
2026-01-06 19:00 - 21:00, 2026-01-13 19:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for Pub Trivia every Tuesday, 7pm-9pm, hosted by Patrick W. Trivia. Trivia is free to play, with prizes for first, second, and third place.
See more events at Doherty’s.

Music Bingo at House of Hops
2026-01-07 18:00 - 20:00 | NC
Join House of Hops every Wednesday, 6pm-8pm for Music Bingo hosted by DJ Special K. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Jazz Nights at The Sycamore
2026-01-07 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Open Mic Night at Fair Game Beverage Company
2026-01-07 18:30 - 21:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Call all performing artists! Fair Game Beverage Company, located at The Plant in Pittsboro, hosts its Open Mic Night on the first Wednesday of every month, 6pm-9pm. Bring your talent – originals, covers, comedy, stories, or poetry! Or just come spectate and listen to local artists. Hosted by Danny Whipple.
Local NC beers, wines, ciders, and craft cocktails will be available at the bar. Local dining available at Kingston 99 Kitchen and Ta Contento. This event is free and takes place indoors. The Plant is wheelchair accessible, and additional accommodations are available upon request. Free parking is available on-site. No pets allowed, please. See more events at The Plant. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

Karaoke at Hops and Berry
2026-01-07 19:00 - 22:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Run Club at Thirsty Skull PBO
2026-01-08 17:00 - 18:30 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro every Thursday, 5pm-6:30pm for Run Club.
See all events at Thirsty Skull Brewing – PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

Bynum Byte Night
2026-01-08 18:00 - 20:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Bynum’s Byte Night happens every other Thursday, 6pm-8pm. It’s a weekly tech hangout for anyone curious about computers, electronics, or AI – whether you’re fixing a glitchy device, exploring creative and design tools, or just want to talk digital life with neighbors. They’ve even got a virtual reality (VR) headset on hand if you want to step into another world for a bit. No pressure, no jargon—just a space to learn, share, and connect. Bring your questions, your projects, or just come see what others are up to. All skill levels welcome!
Contact Helbragga (John G.) at 919.593.3559 with any questions.
See more Bynum Front Porch events.

Live Music at Galloway's
2026-01-09 17:00 - 19:00, 2026-01-10 17:00 - 19:00, 2026-01-14 17:00 - 19:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesday-Saturday, 5pm-7pm. Check out their events calendar to see who’s playing.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

America 250 History Trivia
2026-01-10 10:00 - 12:00 | Chatham Community Library, 197 NC Hwy 87 N, Pittsboro, NC, 27312, United States
Join the Chatham Community Library for America 250 History Trivia on Sat, Jan 10, 10am-12pm. America 250 history trivia is a set of fun questions or facts about U.S. history made to celebrate America’s 250th anniversary in 2026. America 250’s mission is to honor and commemorate the 250th anniversary of the signing of the Declaration of Independence, marking America’s Semiquincentennial.
This FREE, family-friendly event is open to the public. No registration is required. The event will take place indoors in the Chatham Community Library’s Holmes Family Meeting Room. The Chatham Community Library is ADA-compliant, including wheelchair-accessible parking, entrances, seating, common spaces, walkways, and restrooms. The Holmes Family Meeting Room has an automatic door opener. Free parking is available outside the library. Pets are not allowed – please leave your furry friends at home.
This event is part of our Chatham Celebrates America 250 initiative. See more America 250 events. See more events at the Chatham Community Library.

Live Music: Dr. Scott
2026-01-10 15:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Dr. Scott, hosted on select days throughout 2026. Check out these upcoming performances:

Sat, Jan 10, 3pm-5pm.
Sun, Feb 1, 2pm-4pm.

Dr. Scott is a fingerstyle guitarist and vocalist with 15 years of experience performing a genre-spanning repertoire, including blues, jazz, folk, Spanish, classical guitar, bluegrass, country, and classic rock. Known for his technical guitar playing and rich baritone vocals, he delivers smooth melodies, thumb-thumping rhythms, and familiar favorites sure to get your feet tapping and your knees slapping. Featuring covers of artists like John Prine, Dave Van Ronk, Ray Charles, Doc Watson, Leon Redbone, the Beatles, and the occasional original.
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they are in a position of having to cancel, they will try to do so well in advance. Free parking is available onsite. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.
