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  • Holly Jolly Christmas Party 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 Holly Jolly Christmas Party and their first-ever cookie exchange on Sat, Dec 20, 5pm-8pm. Wear your best ugly Christmas sweater and delight in a hot cocoa bar...

  • 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...

  • 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...

  • The Graveyard Shift at The MOD

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

    Join The MOD for The Graveyard Shift, a monthly dark disco dance party. All are welcome. This event is for ages 21+ and the cover is $5 per person. Upcoming event dates and guest DJs are listed below: Sat, Jun 28, 8pm-12am Mouse the DJ. Fri, Jul 18, 8pm-12am Guest DJ APTIK. Sat, Aug 16, 8pm-12am Guest DJ...

  • Christmas Market at The City Tap

    Events at City Tap
    City Tap 89 Hillsboro Street, Suite B, Pittsboro, NC, United States

    Attention, last-minute shoppers! Join The City Tap for a Christmas Market on Sun, Dec 21, 11:30am-3:30pm. Get your host gifts, stocking stuffers, or spoil yourself, all while enjoying a cup of cheer! Vendors...

  • Winter Solstice Forest Bathing Walk

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

    Join The Plant and Rewild Within for a Winter Solstice Forest Bathing Walking on Sun, Dec 21, hosted: 1pm-2:15pm. 2:30pm-3:45pm. Two sessions are available for this gentle, reflective experience to ground, express gratitude, and welcome the return of the light guided by Amy Allen. Connect with your senses, nature, and yourself- no experience needed. The session will end with...

  • 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...

  • 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....

  • Winter Solstice Forest Bathing Walk

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

    Join The Plant and Rewild Within for a Winter Solstice Forest Bathing Walking on Sun, Dec 21, hosted: 1pm-2:15pm. 2:30pm-3:45pm. Two sessions are available for this gentle, reflective experience to ground, express gratitude, and welcome the return of the light guided by Amy Allen. Connect with your senses, nature, and yourself- no experience needed. The session will end with...

  • 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...

  • 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...

  • Fearrington Farmers Market

    Fearrington Farmers Market
    Fearrington Farmers Market E Camden, Pittsboro, NC, United States

    The Fearrington Farmers Market is a producers-only market open Mar-Oct, Tuesdays, 4pm-6pm, and Nov-Feb, Tuesdays, 3pm-5pm, year-round in Fearrington Village. Bring reusable tote bags and plan to explore the many local vendors. You also might chat with the farmers, see old friends, or meet new ones! It’s a welcoming, inclusive, and friendly atmosphere that encourages healthy,...

  • Yoga at Bynum Front Porch

    Yoga at Bynum General Store
    Bynum General Store 950 Bynum Rd, Bynum, NC, United States

    Unwind and recharge with Yoga at Bynum Front Porch, hosted every Tuesday, 6pm-7pm at the Historic Bynum General Store. This all-levels class offers a welcoming space to stretch, breathe, and connect with...

  • Run Club at House of Hops

    Events at House of Hops

    Join House of Hops every Tuesday, 6pm-8pm for Run Club and 20%-off mixed six pack. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

  • 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...

  • 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...

  • 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...