Pittsboro-Siler City Convention & Visitors Bureau

Jazz Nights at The Sycamore
2025-05-07 18:00 - 21:00, 2025-05-14 18:00 - 21:00 (America/New_York) | 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
2025-05-07 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
2025-05-07 19:00 - 22:00, 2025-05-14 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
2025-05-08 17:00 - 18:30, 2025-05-15 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
2025-05-08 18:00 - 20:00, 2025-05-15 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
2025-05-08 18:00 - 21:00, 2025-05-09 18:00 - 21:00, 2025-05-10 18:00 - 21:00, 2025-05-13 18:00 - 21:00, 2025-05-15 18:00 - 21:00, 2025-05-16 18:00 - 21:00, 2025-05-17 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.

Euchre Mondays at bmc
2025-05-12 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
2025-05-13 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.

Music Bingo at Hops and Berry
2025-05-13 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
2025-05-13 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.

Poetry at The Plant
2025-05-14 18:00 - 19:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Come out for Poetry at The Plant on the second Wednesday of every month, 6pm-7pm. Enjoy an hour of original poetry from regional poets in the Fair Game Beverage Company Wheelhouse Tasting Room (and enjoy a drink and meal while you’re at it)!
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
2025-05-14 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.

3rd Friday Artist Receptions
2025-05-16 17:00 - 20:00 | Pittsboro Gallery of Arts, 44 Hillsboro Street, Pittsboro, NC, 27312, United States
Pittsboro Gallery of Arts is pleased to announce the return of 3rd Friday Artist Receptions. Each month, they highlight a new artist and offer an opportunity to meet them and ask about their work. Beverages and snacks will accompany. These events are held every third Friday, 5pm-8pm. Featured artists are announced on their Facebook Page.
See more Pittsboro Gallery of Arts events.

Live Music: Deep Black River Band
2025-05-16 18:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Deep Black River Band on Fri, May 16, 6pm-9pm. The band will be bringing 90’s and classic rock tunes!
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 pets are allowed. This event is free! See all events at The Plant.

Karaoke at Thirsty Skull
2025-05-16 19:00 - 21:00 | Thirsty Skull Brewing, 915 N Second Ave, Siler City, NC, 27344, United States
Join Thirsty Skull Brewing – Siler City on the third Friday of each month, 7pm-9pm for Karaoke with JV Jams.
See all events at Thirsty Skull Brewing. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music: Guy Wire
2025-05-16 19:30 - 21:30 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Guy Wire on Fri, May 16, 7:30pm-9:30pm.
This event takes place on the patio at The City Tap. There is no cover charge for this event, but tipping the musicians is recommended. See all events at City Tap.

Live Music: The Petty Thieves
2025-05-17 14:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with The Petty Thieves on Sat, May 17, 2pm-5pm, in celebration of Lilly Den’s third anniversary. The Petty Thieves are a good time band out of Pittsboro playing their favorite Tom Petty songs.
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 pets are allowed. This event is free! See all events at The Plant.

Live Music: Old Play
2025-05-17 18:00 - 21:00 | Havoc Brewing Company, 39 West Street, Pittsboro, NC, 27312, United States
Havoc Brewing Company presents Live Music with Old Play. Performances take place on the following dates:

Sat, May 17, 6pm-9pm.
Sat, Jul 26, 6pm-9pm.

Based in the Raleigh/Durham/Cary area, Old Play has performed crowd-pleasing rock classics for the last 10 years. Old Play shows are high-energy entertainment featuring some of the most loved songs of the past 4 decades, from AC/DC to ZZ Top, and everything in between! You’ll surely be dancing, singing along, air-drumming, or fist-pumping as Old Play belts out their repertoire of classic rock anthems and ballads – and maybe even a little country!
More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music: Shot Gun Ragtime
2025-05-17 19:30 - 21:30 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Shot Gun Ragtime on Sat, May 17, 7:30pm-9:30pm.
This event takes place on the patio at The City Tap. There is no cover charge for this event, but tipping the musicians is recommended. See all events at City Tap.

Live Music: Chosen Family Card
2025-05-18 13:00 - 16:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Chosen Family Card on Sun, May 18, 1pm-4pm.
Chosen Family Card emerged from the pandemic when a married couple, Aaron (lead guitar) and Julie Keane (lead vocals) and their best friend, Deborah Usinger (violin) played music and joined an online community open mic series so that they wouldn’t go stir crazy! What began as music sessions to break the monotony of lockdown quickly evolved into something more —a rock and pop cover band that celebrates the bonds we choose rather than inherit. The band is now joined by good friend Dan Radzicki on bass and our neighbor, Dale Hammer, on drums.
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. 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 pets are allowed. This event is free! See all events at The Plant.
