Pittsboro-Siler City Convention & Visitors Bureau

Live Music at Galloway's
2026-01-28 17:00 - 19:00, 2026-01-29 17:00 - 19:00, 2026-01-30 17:00 - 19:00, 2026-02-04 17:00 - 19:00, 2026-02-05 17:00 - 19:00 (America/New_York) | 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.

Improv Theatre at The Plant
2026-01-28 18:00 - 19:30 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
The Plant hosts Improv Theatre every fourth Wednesday, 6pm-7:30pm. Enjoy some spontaneous fun together as this trio of improvisers creates a show for you in real time based on your suggestions! Featuring Dan Sipp, Jane Allen Wilson, and Anoo Tree Brod, each actor, teacher, and facilitator of community improv workshops, who delight in sharing the improv muse with one and all! They have each branched into their own improv directions and companies and are thrilled to reunite in Pittsboro to share this dynamic art form with the Plant community!
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.

Music Bingo at House of Hops
2026-01-28 18:00 - 20:00, 2026-02-04 18:00 - 20:00 | North Carolina
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
2026-01-28 18:00 - 21:00, 2026-02-04 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.

Karaoke at Hops and Berry
2026-01-28 19:00 - 22:00, 2026-02-04 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
2026-01-29 17:00 - 18:30, 2026-02-05 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.

Opinionation Trivia at House of Hops
2026-01-29 18:00 - 20:00, 2026-02-05 18:00 - 20:00 | 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.

Live Piano Music at The Sycamore
2026-01-29 18:00 - 21:00, 2026-01-30 18:00 - 21:00, 2026-02-03 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.

Blues Jam at The MOD
2026-01-29 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.

Stamp-Making Pop-Ups at The Plant
2026-01-30 18:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Stamp-Making Pop-Ups, hosted on select dates in January. Print handmade stamps on t-shirts, totes, towels, and various other fabric products. Price ranges from $10-$20, depending on the fabric chosen. Available on a first-come, first-served basis. All classes are beginner-friendly. Pop-ups will take place on the following dates:

Fri, Jan 23, 6pm-8pm.
Fri, Jan 30, 6pm-8pm.

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.
Free parking is available on-site. 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.

Salsa Class at bmc
2026-01-30 18:00 - 21:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join bmc brewing for a Salsa Class on Fri, Jan 23, 6pm-9pm. Are you ready to dance? bmc brewing and Ta Contento are bringing you a night of dancing! Learn and show off your Salsa and Bachata moves! The Beginner Class runs from 6pm-7pm and is followed by Open Dancing from 7pm-9pm. The cost is $5 per person.
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.

Cactus Cowgirl's Plant Bingo Night
2026-01-30 19:00 - 21:00 | Cactus Cowgirl, 19 Hillsboro Street, Pittsboro, 27312, United States
Join Cactus Cowgirl for Plant Bingo Night hosted on the last Friday of every month, 7pm-9pm. Get ready for a night of plants, prizes, and pure fun. There will be seven exciting rounds of bingo, each packed with chances to win awesome planty prizes—from houseplants to fun goodies you’ll love. Whether you’re a seasoned plant parent or just getting started, this is the perfect way to hang out, meet fellow plant lovers, and enjoy a laid-back, laughter-filled evening. Bring your friends and get ready to shout BINGO! Spaces are limited, so sign up early and don’t miss out on one of their most fun events of the month! Tickets are $24.80 per person and include:

7 rounds of Bingo
2″ Mini Cactus
10% off the entire store during the event.
A cactus Cowgirl Saddle (Goodie) Bag

See more events at Cactus Cowgirl.

Wheelhouse Music Sessions: The Jive Bombers
2026-01-30 19:30 - 21:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant and Fair Game Beverage Company for Wheelhouse Music Sessions: The Jive Bombers on Fri, Jan 30, 7:30pm-9:30pm. Robert Waldrop returns to The Wheelhouse but this time as the main act with his band, The Jive Bombers!
The Jive Bombers are 4 like-minded folks who want to play good songs and make them sound pleasing to your ears. What folks call “Americana” is what NearBlind James Shoe and Harmonica Bob Waldrop have been playing together since 1979 as a duo and in multiple bands over the years. They are pretty much joined at the hip musically. John and Kim Dengler joined in 2019 to fill out the sound and singing, and to allow for different directions. Lots of Harmony and on-key singing! Songs include a few originals and others that date as far back as the 1930’s and up to now, including blues, soul, gospel, primitive country, rockabilly, R & B, and all those other good ‘ns. Jumpin’-Jivin’-Swingin’-Swayin”! No draggin mess cause folks want somethin with some PEP. It’ll be cold outside but hot inside!
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.
The admission cost is $15 per person. Free parking is available onsite. The event takes place indoors at The Plant. 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.

Live Music: Sammy and Jared at Hops and Berry
2026-01-30 19:30 - 22:30 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Live Music with Sammy and Jared on Fri, Jan 30, 7:30pm-10:30pm.
This event is free and takes place indoors. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. This space is wheelchair accessible. Schedules are subject to change – please confirm using the event organizer’s website for planning your visit. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music with The MixTapes at The MOD
2026-01-31 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Live Music with The MixTapes on Sat, Jan 31, 7pm-10pm. The MixTapes are a five-piece band from the North Carolina Triangle area that covers songs from Linda Ronstadt to Fleetwood Mac, Miranda Lambert to Whitney Houston, AC/DC to Van Halen, Bruce Springsteen to Billy Joel, and plenty of Stones, Beatles, and others. The band features Wendy Kreitman on lead vocals, Art Champagne on guitar, Sean Timmons on bass and vocals, Nancy Bierman on vocals, keys, and percussion, and Dana T. on drums.
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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 Club at House of Hops
2026-02-03 18:00 - 20:00 | North Carolina
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.

Music Bingo at Hops and Berry
2026-02-03 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
2026-02-03 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.

Open Mic Night at Fair Game Beverage Company
2026-02-04 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.
