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  • 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.

  • Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill

    Events at The Plant
    The Plant 220 Lorax Lane, Pittsboro, NC, United States

    Join Fair Game Beverage Company in the Wheelhouse for Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill on Tue, Dec 23, 7:30pm-9:30pm. Jennifer Curtis returns for another Wheelhouse show, accompanied by Matthew Greenslade with festive Christmas tunes—plus some special guests! Matthew Greenslade will bring the holiday spirit and perform music from The Real Christmas...

  • Christmas Eve Party at Vino!!

    Vino!! Wine Shop Tastings and Events
    Vino!! Wine Shop 89 Hillsboro Street, Suite A, Pittsboro, NC, United States

    Join Vino!! Wine Shop for a Christmas Eve Party on Wed, Dec 24, 12pm-5pm. Celebrate the end of the year and the holidays by wearing your ugly sweaters or Christmas PJs. There will be holiday cocktail specials and a cookie exchange! This event takes place indoors. All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and...

  • 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 up to belt out their favorites—whether that's a power ballad, a crowd-singalong anthem, or a deep cut only you remember. With a supportive, come-as-you-are vibe,...

  • 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.

  • 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 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...

  • 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.

  • 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...

  • Line Dancing Classes at Chatham Mills

    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 Line Dancing Classes at Chatham Mills, hosted by Forest Hall at Chatham Mills and the Chatham Social Club every Friday, 11am-12pm. The cost is...

  • Run and Roam Fridays at The Plant

    Events at The Plant
    The Plant 220 Lorax Lane, Pittsboro, NC, United States

    Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country...

  • 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 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: Jason Damico

    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 Jason Damico. Performances take place on the following dates: Sat, Jun 7, 7:30pm-10:30pm. Sat, Aug 23, 7:30pm-10:30pm. Sat, Oct 25, 7:30pm-10:30pm. Sat, Dec 27, 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....

  • Crafternoons at Clapping Hands Farm

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

    Join Clapping Hands Farm for Crafternoons hosted every Sunday, December 2025-February 2026, 1pm5pm. This is a drop-in crafting circle, not a class. Bring a project you’re already working on, or join many of...

  • Euchre Mondays at bmc

    Euchre Mondays at bmc
    bmc brewing 213 Lorax Lane, Pittsboro, NC, United States +1 more

    Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. This weekly gathering is built around the classic trick-taking card game. No experience is needed — a fantastic regular euchre group is happy to bring newcomers up to speed, so you can show up solo or with friends and jump right in. Monday...

  • Paint and Pint Night at House of Hops

    Events at House of Hops
    House of Hops 112 Russet Run, Pittsboro, NC, United States

    Join House of Hops for a Paint and Pint Night on Mon, Dec 29, 6:30pm-8:30pm. Come cozy up at House of Hops while Wine & Design guides you through a step-by-step instructed paint class on pre-sketched canvases. Tickets are $25 per person. No experience required. Arrive 30 minutes early to order your drinks! Wine & Design will have...