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  • 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...

  • 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 include:  Build-your-own cookie platters, breakfast pastries, and more from Confectious Creations. Goat's milk soap and skincare products from Toad Hollow Soapery. Potted giant amaryllis, dried...

  • 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...

  • 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 regular euchre group is happy to bring newcomers up to speed, so you can show up solo or with friends and jump right in. Monday...

  • 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...

  • 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 the community - bring your mat and a positive spirit. This event is free to attend, with a suggested donation of $15. Directions. Year-round events,...

  • 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 include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here. See more events at The Sycamore at Chatham Mills.

  • 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 a line before anyone else. It's a low-key, high-energy way to spend a weeknight, and the format welcomes everyone from casual listeners to die-hard music...

  • 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 more events at Doherty's.

  • Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill

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

    Join Fair Game Beverage Company in the Wheelhouse for Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill on Tue, Dec 23, 7:30pm-9:30pm. Jennifer Curtis returns for another Wheelhouse show, accompanied by Matthew Greenslade with festive Christmas tunes—plus some special guests! Matthew Greenslade will bring the holiday spirit and perform music from The Real Christmas...

  • Christmas Eve Party at Vino!!

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

    Join Vino!! Wine Shop for a Christmas Eve Party on Wed, Dec 24, 12pm-5pm. Celebrate the end of the year and the holidays by wearing your ugly sweaters or Christmas PJs. There will be holiday cocktail specials and a cookie exchange! This event takes place indoors. All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and...