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  • 2025 Clayworxs Studios Show

    Clayworx Studios 136 Fayetteville St., Suite G, Pittsboro, United States

    This is the event of the season that you don't want to miss! The 4th Annual Clayworxs Studios Show is happening Sat, Dec 13, 5pm-8pm. Join them for an "Enchanting Evening" event...

  • Pittsboro Christmas Parade

    Downtown Pittsboro Events
    Downtown Pittsboro Hillsboro Street, Pittsboro, NC, United States

    An annual tradition returns to downtown with the Pittsboro Christmas Parade on Sun, Dec 14, 3pm-5pm. There will be beautifully decorated floats built by local groups and businesses, filled to the brim with...

  • Holiday Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings...

  • Holiday Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings...

  • Holiday Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings...

  • Jingle and Mingle with Chatham Pride Alliance

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

    Join Chatham Pride Alliance for their second annual Jingle and Mingle on Thu, Dec 18, 6pm-9pm at Thirsty Skull Brewing - Pittsboro. Get ready for a festive evening of community, connection, and cheer! This...

  • Holiday Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings...

  • Donald Davis Annual Storytelling

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

    Fearrington Village is delighted to welcome back their beloved friend and storyteller, Donald Davis, for their Annual Storytelling on Sat, Dec 20, 11am-12pm and Sun, Dec 21, 2pm-3pm. After a hiatus last year, their fundraiser for the Chatham food pantry, CORA, is back. And they will tell you, the holidays just don’t start at McIntyre's until Donald arrives in Fearrington....

  • Holiday Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings...

  • Donald Davis Annual Storytelling

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

    Fearrington Village is delighted to welcome back their beloved friend and storyteller, Donald Davis, for their Annual Storytelling on Sat, Dec 20, 11am-12pm and Sun, Dec 21, 2pm-3pm. After a hiatus last year, their fundraiser...

  • Annual Dueling Sommelier Dinner

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

    'Tis the season for the Annual Dueling Sommelier Wine Dinner with Vino!! Wine Shop on Sun, Dec 21, 5:45pm-8:45pm. Newcomer Sommelier Michael Maller of Orsini Wines is ready to take on former...

  • New Year’s Eve Dinner at The Sycamore

    Events at Chatham Mills
    The Sycamore at Chatham Mills 480 Hillsboro Street, Suite 500, Pittsboro, NC, United States

    Join The Sycamore at Chatham Mills for a New Year's Eve Dinner on Wed, Dec 31, 5pm-8:30pm. They won't be ringing in the new year, but they will have a beautifully curated Chef's Tasting Menu ($110 per person, including one glass of champagne) designed to elevate your last evening of the year with rich flavors, seasonal inspiration,...

  • A Roving New Year’s Eve!

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

    Welcome 2026 with A Roving New Year's Eve at The Plant, Wed, Dec 31, 6pm-Thu, Jan 1, 12am. Join The Plant on New Year's Eve for "one last crawl" to end 2025!...

  • Quiltmaker’s Annual New Year’s Open House

    Quiltmaker Cafe 75 W Salisbury St, Pittsboro, NC, United States

    Join your community members and Quiltmaker Cafe for their Annual New Year's Open House on Thu, Jan 1pm-4pm. Start 2026 right with desserts, games, and community at Quiltmaker's future home (opening soon). This celebration is an Open-House, child-friendly event, so please stay for as long as you are able. Volunteer opportunities are available. Participating businesses include Circle City...

  • In With The New at Reclamation

    Reclamation Events
    Reclamation 102 Hillsboro St, Pittsboro, NC, United States

    Join Reclamation for their annual "In With The New" evening on Fri, Jan 2, 4pm-7pm. They will be closed starting Mon, Dec 29-Thu, Jan 1, and will re-open on Fri, Jan 2...

  • 2nd Annual Chatham Farm Forever: Farmland Preservation and Conservation Day

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

    Join The Chatham County Farmland Preservation Program for their 2nd Annual Chatham Farm Forever: Farmland Preservation and Conservation Day on Thu, Jan 15, 8:30am-3pm at the Chatham County Agriculture & Conference Center (CCACC). Chatham Farms Forever is a free, daylong workshop program for working landowners that provides resources on farmland preservation and conservation management. Speakers will present on a...

  • 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...

  • 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...