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  • 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, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country...

  • Scarecrow Shenanigans (All Ages)

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

    Scarecrow Shenanigans (All Ages) is the perfect October workshop for the entire family! Build your scarecrow using a wooden frame, colorful clothing, straw, and a touch of imagination. Get ready to bring your scarecrow to life with quirky personalities and funny faces. The recommended short supply list is available upon registration. Instructed by Leigh Babcock. This...

  • 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...

  • Save The Duck – Fall 2025 Trunk Show

    Events at Fearrington Village
    Dovecote Home and Garden, Nest, and Sprout 250 Market Street, Pittsboro, NC, United States

    Fri, Oct 3-Sat, Oct 4, 10am-5pm, Dovecote will host designer Save The Duck as part of their Fall 2025 Trunk Show series. Seth is back with Save the Duck, and he’ll...

  • Huckleberry Trail Farm Fall Festival

    Huckleberry Trail Farm Events
    Huckleberry Trail Farm 143 Pleasant Hill Church Rd, Siler City, NC, United States

    Visit the Huckleberry Trail Farm Fall Festival for a corn maze, a pumpkin patch (select a pumpkin from the vine), a cotton patch, and a fall atmosphere. Find designated quiet areas set up the entire season. The family’s mission is to bring all kids back to the outdoors with the goal of making many of the farm...

  • Egyptian Festival

    Egyptian Festival

    Join Archangel Raphael and Blessed St. John Coptic Orthodox Church for their third annual Egyptian Festival on Sat, Oct 4, and Sun, Oct 5, 12pm-6pm. This family-friendly event will feature delicious Egyptian food, artwork, jewelry,...

  • Carolina Brewery Fall Music Series

    Carolina Brewery and Grill Events
    Carolina Brewery & Grill 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, United States

    Take in live music from local musicians on the patio at Carolina Brewery and Grill during their Fall Music Series. Hosted Saturdays, September-October, 5:30pm-8pm. See specific dates and performers listed...

  • 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...

  • First Sunday Sound Bath

    First Sunday Sound Bath at Starrlight Mead
    Starrlight Mead 130 Lorax Ln, Pittsboro, NC, United States +1 more

    At Starrlight Mead's First Sunday Sound Bath, cathedral-like acoustics in this space bring a sense of reverence and play to these sessions. Think of it like a non-dogmatic sonic church....

  • The Wanderer’s Market

    Events at West End
    West End Kitchen and Catering Pittsboro, North Carolina, United States

    Join West End for The Wanderer's Market hosted every first Sunday, May-Oct, 12pm-4pm. Markets include a new music guest each month, great food and drink from West End, and shopping at Finders...

  • First Sunday Pittsboro

    Downtown Pittsboro Events
    Pittsboro Pop-Up Park West Salisbury Street, Pittsboro, North Carolina, United States

    First Sunday Pittsboro takes place the first Sunday, Apr-Dec, 12pm-4pm.  Come out and enjoy a bit of Pittsboro’s downtown charm. This family-friendly event is free to attend. Artisans, non-profits, and local businesses...

  • Oktoberfest at The Plant

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

    Come celebrate Oktoberfest at The Plant on Sun, Oct 5, 12pm-6pm. The festivities will include local bratwurst and Bavarian Pretzels, live music by Folkknot from 2pm-5pm, a kid's costume contest, a stein holding contest,...

  • Egyptian Festival

    Egyptian Festival

    Join Archangel Raphael and Blessed St. John Coptic Orthodox Church for their third annual Egyptian Festival on Sat, Oct 4, and Sun, Oct 5, 12pm-6pm. This family-friendly event will feature delicious Egyptian food, artwork, jewelry,...

  • Huckleberry Trail Farm Fall Festival

    Huckleberry Trail Farm Events
    Huckleberry Trail Farm 143 Pleasant Hill Church Rd, Siler City, NC, United States

    Visit the Huckleberry Trail Farm Fall Festival for a corn maze, a pumpkin patch (select a pumpkin from the vine), a cotton patch, and a fall atmosphere. Find designated quiet areas set...

  • Live Music: Folkknot

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

    Join The Plant for Live Music with Folknot on Sun, Oct 5, 2pm-5pm. Folkknot is a seafaring six-piece band based in Greensboro, North Carolina. Never afraid to sail against the wind,...

  • Tap Dancing – Advanced

    Chatham County Parks and Recreation Events
    Chatham Grove Community Center 1301 Andrews Store Road, Pittsboro, United States

    Tap Dancing - Advanced is for experienced tappers who are skilled at named steps and can perform intricate choreography. Tap shoes are recommended but not required. This class occurs every Monday, Sep 8-Oct 13, 1pm-2pm. Registration opens Wed, Aug 15, and closes Mon, Sep 15. This event is held indoors at the Chatham Grove Community Center by...

  • Makers: Recycle, Upcycle, and Create!

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

    At Makers: Recycle, Upcycle, and Create, you'll be challenged to combine DIY craft supplies with repurposed household discards and recyclables in generating artful expressions and upcycled decor! This four-week session takes place every Monday, Oct 6-Oct 27, 6pm-7:30pm. Registration opens Mon, Aug 18, and closes Mon, Sep 29. This event is held indoors at the new Chatham...