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  • Run Club at House of Hops

    Events at House of Hops

    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

    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 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

    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 a line before anyone else. It's a low-key, high-energy way to spend a weeknight, and the format welcomes everyone from casual listeners to die-hard music...

  • 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 more events at Doherty's.

  • 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.  

  • Crokinole at Fair Game

    Crokinole at Fair Game Beverage Company
    Fair Game Beverage Company 192 Lorax Lane, Pittsboro, NC, United States +1 more

    Try your hand at an obscure Canadian board game with Crokinole at Fair Game Beverage Company, hosted every third Wednesday, 6pm-8pm in the Wheelhouse. Crokinole is a classic Canadian tabletop game — think shuffleboard meets curling, shrunk onto a round wooden board. It's easy to learn in a single round and genuinely fun whether you're a first-timer or a...

  • 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...

  • 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...

  • Pittsboro Farmers Market

    Farmers Markets
    Pittsboro Pop-Up Park West Salisbury Street, Pittsboro, North Carolina, United States

    The Pittsboro Farmers Market is open year-round and features select items from within a 50-mile radius. They are open every Thursday, 3pm-6pm at Pittsboro's Pop-Up Park. The product-only market features...

  • 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.  

  • Opinionation Trivia at House of Hops

    Events at House of Hops
    House of Hops 112 Russet Run, Pittsboro, NC, 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...

  • 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 include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here. See more events at The Sycamore at Chatham Mills.

  • Live Music with Mondo Guitaro at Thirsty Skull

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

    Join Thirsty Skull Brewing - Pittsboro for Live Music with Mondo Guitaro, hosted every third Thursday,7pm-9pm. Come hang out and listen to the awesome sound of Mondo Guitaro. “Lonesome Tones...

  • Blues Jam at The MOD

    Events at The MOD
    The Modern Life Deli & Drinks 46 Sanford Road, Pittsboro, NC, 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...

  • Free Public Domain Movie Night at bmc

    Free Public Domain Movie Night at bmc
    bmc brewing 213 Lorax Lane, Pittsboro, NC, United States +1 more

    Join bmc brewing for a Free Public Domain Movie Night hosted every Thursday, 7pm-10pm. Films enter the public domain in the United States when their copyright protection expires, which typically happens 95 years after publication for older works, or if owners fail to follow registration and renewal requirements. As of 2026, all films released before 1930 are...