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  • Live Music: Mondo Guitaro at The City Tap

    Events at City Tap
    City Tap 89 Hillsboro Street, Suite B, Pittsboro, NC, United States

    Join The City Tap for Live Music with Mondo Guitaro on Tue, Jan 27, 6pm-8pm. “Lonesome Tones for High Plains Drifters”: Mondo Guitaro performs spaghetti western, surf, and 1960s-style instrumentals arranged...

  • Live Piano Music at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, 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...

  • Music Bingo at Hops and Berry

    Music Bingo at Hops & Berry
    Hops & Berry 120 Mosaic Blvd, Suite 100, Pittsboro, NC, United States

    Come to Hops and Berry-Pittsboro for Music Bingo every Tuesday, 7pm-9pm. Instead of numbers, players listen for tracks and mark their cards as they recognize each tune, racing to fill...

  • Pub Trivia at Doherty’s

    Events at Doherty’s
    Doherty's Irish Pub and Restaurant 56 Sanford Road, Pittsboro, NC, 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...

  • Hampton Inn and Suites – Pittsboro Career Fair

    MOSAIC at Chatham Park Events
    Hampton Inn & Suites by Hilton Pittsboro 324 Freedom Parkway, Pittsboro, United States

    Introducing Hamptonality to Pittsboro! Join Hampton Inn and Suites – Pittsboro for a Pittsboro Career Fair on Wed, Jan 28, 10am-5pm. They are on the lookout for enthusiastic individuals to join their team and...

  • Live Music at Galloway’s

    Events at Fearrington Village
    The Belted Goat Market Street, Pittsboro, North Carolina, 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

    Improv Theatre at The Plant
    Fair Game Beverage Company 192 Lorax Lane, Pittsboro, NC, United States +1 more

    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!...

  • Adult Begin to Sew Series with Checkered Tulip

    Events at Checkered Tulip
    Checkered Tulip 35 West Chatham Street, Pittsboro, NC, United States

    Join Checkered Tulip for this Adult Begin to Sew Series, hosted on select days throughout 2026. This workshop provides a structured introduction to essential sewing techniques for beginners or those...

  • Jazz Nights at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, 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...

  • Acoustic Irish Music Seisiún

    Events at Doherty’s
    Doherty's Irish Pub and Restaurant 56 Sanford Road, Pittsboro, NC, United States

    Join Doherty's Irish Pub & Restaurant for an Acoustic Irish Music Seisiún on the last Wednesday of every month, 6pm-9pm. Whether you're just beginning your music journey, a seasoned pro, or just love to listen, bring your instruments and passion for Irish music for an evening of lively tunes and great company. Musicians will be upstairs. See...

  • Karaoke at Hops and Berry

    Karaoke at Hops and Berry
    Hops & Berry 120 Mosaic Blvd, Suite 100, Pittsboro, NC, United States

    Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. The taproom's weekly Karaoke night turns its live-entertainment stage over to the crowd, where regulars and first-timers alike line...

  • Winter 2026 Homeschool Camp at Clapping Hands Farm

    Clapping Hands Farm Events
    Clapping Hands Farm 3348 Alston Chapel Road, Pittsboro, NC, United States

    Join Clapping Hands Farm for their Winter 2026 Homeschool Camp, hosted every Thursday, January 8-February 12, 9am-3:30pm. Clapping Hands is an arts and nature camp and retreat with a special love for community. Our homeschool camp workshops include visual arts, crafts, music, theater, and dance, as well as engineering, building, nature exploration, game creation, and more! GENERAL...

  • Storytime with Johanna Banana

    Events at Fearrington Village
    McIntyre's Books 220 Market Street, Pittsboro, NC, United States

    Join McIntyre's Books for Storytime with Johanna Banana, hosted every Thursday, 10:30am-11:30am. McIntyre’s bookseller Johanna Banana leads this weekly storytime. The books and songs shared are primarily for toddlers and preschoolers,...

  • Winter Sowing Pollinator Flowers

    Chatham County Parks and Recreation Events
    The Arts Center 964 East Street, Suite 105, Pittsboro, NC, United States

    At Winter Sowing Pollinator Flowers on Thu, Jan 29, 4pm-5pm, you'll join the Therapeutic Horticulture Extension Master Gardeners of Chatham County to learn about the benefits of growing native and pollinator flowers and how to winter sow. Winter sowing is the art of planting seeds in terrarium-like conditions and setting them outside to let nature work its...

  • Run Club at Thirsty Skull PBO

    Events at Thirsty Skull PBO
    Thirsty Skull Brewing - Pittsboro 684 West Street, Pittsboro, NC, 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.

  • Live Music at Galloway’s

    Events at Fearrington Village
    The Belted Goat Market Street, Pittsboro, North Carolina, 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.  

  • 8 Week Social Bolero – Intermediate Level

    Events at Chatham Mills
    Forest Hall at Chatham Mills 480 Hillsboro Street, Suite 350, Pittsboro, NC, United States

    Build your skills on the dance floor with this 8 Week Social Bolero - Intermediate Level, hosted by the Chatham Social Club at the Forest Hall at Chatham Mills. Learn...