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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 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...

  • Our State Book Club: History, Mystery, and Dracula

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

    Join McIntyre's Books for an Our State Book Club: History, Mystery, and Dracula - An Evening with Elizabeth Kostova on Wed, Oct 29, 7pm-8:30pm in the Fearrington Barn. Get ready for a spellbinding evening of conversation with internationally best-selling author Elizabeth Kostova, whose gothic thriller The Historian is Our State's October Book Club selection. The New York Times...

  • 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,...

  • Annual NC Truck Camper Rally

    Chatham Sports Alliance
    Jordan Lake State Recreation Area - Vista Point Access 2498 North Pea Ridge Road, Pittsboro, NC, United States

    D&H RV & Marine hosts their Annual NC Truck Camper Rally on Thu, Oct 30-Sun, Nov 2, 2025. Whether you're a truck camper owner or enthusiast, come enjoy the weekend at...

  • Fall for Literacy Luncheon

    Chatham County Agriculture & Conference Center Events
    Chatham County Agriculture & Conference Center 1192 US-64 W, Pittsboro, NC, United States

    Join Chatham Literacy for their Fall for Literacy Luncheon on Thu, Oct 30, 11am-2pm at the Chatham County Agriculture and Conference Center (CCACC). National columnist, award-winning journalist, popular TED Talk speaker, and author Steven...

  • 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.

  • Halloween Bash at Mystic Mocha

    Mystic Mocha Events
    Mystic Mocha 111 Siler City Crossing, Siler City, United States

    Come out to Mystic Mocha in Siler City for a Halloween Bash on Thu, Oct 30, 5pm-7pm. It's time to dust off those costumes and prepare for a frightfully good night of thrilling fun, wicked music, and Halloween-themed drinks. See more events at Mystic Mocha.

  • 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...

  • Pumpkins on the Bridge – Halloween at Bynum Front Porch

    Bynum Front Porch Music
    Bynum General Store 950 Bynum Rd, Bynum, NC, United States

    Get ready for Pumpkins on the Bridge - Halloween at Bynum Front Porch on Fri, Oct 31, 3pm-11pm  at the historic Bynum Bridge. As the sky starts to turn that perfect Carolina gold, the real magic begins. Neighbors carry their jack-o’-lanterns to the old Bynum Bridge, closed to cars, wide open to everyone. One by one, candles...

  • Halloween at The Plant

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

    Come celebrate Halloween at The Plant on Fri, Oct 31, 4pm-9pm. There will be a Bazaar Night Market featuring local vendors, arts and crafts, a costume parade and contest, trick-or-treating,...

  • Weekly Free Tastings at Vino!! Wine Shop

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

    Weekly free tastings at Vino!! Wine Shop are hosted every Friday. Experts share their picks of wines with varied pricing and from diverse locations. Tasting details, including which wines will be served, are shared on their Facebook Page and in their newsletters. All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country...

  • 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,...

  • 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...

  • Live Music: Vinnie’s Garage

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

    Join The Plant for Live Music with Vinnie's Garage on Fri, Oct 31, 6pm-9pm. Vinnie's Garage is a local good time rock and roll band covering classic rock songs from the...

  • Halloween Bash at The MOD

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

    Join The MOD and locals The Radio and DJ Mouse for a Halloween Bash on Fri, Oct 31, 6pm-Sat, Nov 1, 2am, bringing you the spookiest Halloween festivities around! Dress to impress for their Costume Contest and Parade around the circle. The overall winner gets a table for 8 at The Mod's annual New Year's Eve Gala, including...