• Downtown Pittsboro Events

    Pittsboro Christmas Parade

    Pittsboro 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 cheer and festive spirit, with fun costumes, floats, twinkling lights, and more. Seating will not be provided. Spectators are encouraged to bring their own chairs...

  • Events at Chatham Mills

    Holiday Dinner at The Sycamore

    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...

  • Events at Chatham Mills

    Holiday Dinner at The Sycamore

    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...

  • Events at Chatham Mills

    Holiday Dinner at The Sycamore

    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...

  • Events at Thirsty Skull PBO

    Jingle and Mingle with Chatham Pride Alliance

    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 gathering is more than a party - it's a space to unwind, support one another, and strengthen the ties that make our community shine. Whether...

  • Events at Chatham Mills

    Holiday Dinner at The Sycamore

    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...

  • Chatham County Agriculture & Conference Center Events

    Yu-Gi-Oh World Championship Regional Qualifier

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

    Yu-Gi-Oh World Championship Regional Qualifiers are hosted on select dates at the Chatham County Agriculture and Conference Center for the 2025-2026 season. Regional qualifiers are Tier-2 tournaments in which Duelists compete to earn invites to the World Championship qualifiers, along with exclusive prizes. Participants in the Regional Qualifiers are held to the highest standards of...

  • Events at Fearrington Village

    Donald Davis Annual Storytelling

    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....

  • Events at Chatham Mills

    Holiday Dinner at The Sycamore

    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...

  • Events at Fearrington Village

    Donald Davis Annual Storytelling

    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....

  • Vino!! Wine Shop Tastings and Events

    Annual Dueling Sommelier Dinner

    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 winner Annabel Butler, Level I Sommelier, of Oxford Street Merchants. Chef Regan Stachler has crafted a fantastic four-course meal, which has been shared with both...

  • Events at Chatham Mills

    New Year’s Eve Dinner at The Sycamore

    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,...

  • Events at The Plant

    A Roving New Year’s Eve!

    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! Fair Game Beverage Company, bmc brewing, Starrlight Mead, and Koshu Sake will have festive beverages and creative spirit cocktails, specials, and, of course, sparkling wine...

  • 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...

  • Reclamation Events

    In With The New at Reclamation

    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 at 4pm with lots of new inventory. Adult beverages, free-spirited drinks, snacks, and light appetizers will be provided. Come sip, shop, and kick off the...

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

    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...

  • Events at Fearrington Village

    CrimeScene Killer Cocktail 2026

    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 Mystery Guru Pete Mock is the emcee and creator of the weekend. Pete reads something on the order of 200+ mysteries a year, and he’s the sole...

  • CrimeScene Mystery Bookfest 2026

    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 Mock is the emcee and creator of the weekend. Pete reads something on the order of 200+ mysteries a year, and he’s the sole judge and...

  • Farm Dinners and Tours at Celebrity Dairy

    Open Barn at Celebrity Dairy

    Celebrity Dairy 146 Celebrity Dairy Way, Siler City, NC, United States

    You do not want to miss The Inn at Celebrity Dairy's annual Open Barn hosted every Saturday, Feb 14-Apr 18, 12pm-5pm. Explore the barn, scratch a mama goat behind the ears, and cuddle with some adorable baby goats. This is a great opportunity to learn more about small farm life, with plenty of fun for the...

  • Events at The Plant

    Mardi Gras at The Plant

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

    Get ready to celebrate Mardi Gras at The Plant on Sat, Feb 14, 12pm-6pm. Enjoy a full day of Mardi Gras magic, including jester entertainment, live music, and a high-energy costume-and-music parade led by the Boom Unit Brass Band. Come dressed to impress, bring your friends, and celebrate New Orleans–style at The Plant! ENTERTAINMENT SCHEDULE 12:30pm-3:30pm: Funk Band Jandr....