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  • 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...

  • 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...

  • 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...

  • Wine Class – Blind Tasting 101

    Events at Fearrington Village
    Fearrington House Restaurant 230 Market Street, Pittsboro, United States

    Join Fearrington Village for a Wine Class - Blind Tasting 101 on Thu, Feb 5, 6pm-7pm. During this unique, interactive, and educational session, you'll learn about classic wines! Many people have heard of...

  • 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...

  • Paint and Sip at Hops and Berry

    MOSAIC at Chatham Park Events
    Hops & Berry 120 Mosaic Blvd, Suite 100, Pittsboro, NC, United States

    Come out to Hops and Berry-Pittsboro for a Paint and Sip on Thu, Feb 5, 6pm-8:30pm. Paint a stunning winter wonderland! Your ticket includes all painting supplies, step-by-step guided instructions, and one...

  • 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...

  • 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...

  • Winter Art Sale at the Vineyard

    Events at FireClay Cellars
    FireClay Cellars 1276 Bowers Store Rd, Siler City, NC, United States

    Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy...

  • One Love: Celebrating Bob Marley’s Birthday

    Events at The Plant
    Fair Game Beverage Company 192 Lorax Lane, Pittsboro, NC, United States

    Join Fair Game Beverage Company and Kingston 99 Kitchen for One Love: Celebrating Bob Marley's Birthday on Fri, Feb 6, 5pm-8pm. Dub Fire Reggae Band is bringing the Reggae Rhythms from 5pm-8pm....

  • 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...

  • CrimeScene Killer Cocktail 2026

    Events at Fearrington Village
    Fearrington Barn 500 Market Street, Pittsboro, NC, United States

    Join McIntyre's Books for the biennial return of the CrimeScene Killer Cocktail and Mystery Bookfest during the weekend of Fri, Feb 6-Sat, Feb 7, 2026. The Killer Cocktail will take place on Friday evening, 6pm-9pm. McIntyre’s...

  • Live Music: Eric Tubbs at Hops and Berry

    MOSAIC at Chatham Park Events
    Hops & Berry 120 Mosaic Blvd, Suite 100, Pittsboro, NC, United States

    Come out to Hops and Berry-Pittsboro for Live Music with Eric Tubbs on Fri, Feb 6, 7:30pm-10:30pm. Eric grew up in coastal communities, which influenced his singing and playing, and through the...

  • CrimeScene Mystery Bookfest 2026

    Events at Fearrington Village
    Fearrington Barn 500 Market Street, Pittsboro, NC, United States

    Join McIntyre's Books for the biennial return of the CrimeScene Killer Cocktail and Mystery Bookfest during the weekend of Fri, Feb 6-Sat, Feb 7, 2026. The Mystery Bookfest takes place all day Saturday. McIntyre’s Mystery Guru Pete...

  • Winter Art Sale at the Vineyard

    Events at FireClay Cellars
    FireClay Cellars 1276 Bowers Store Rd, Siler City, NC, United States

    Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy...