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  • Valentine’s Chef’s Tasting Menu at The Sycamore

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

    Whether you're celebrating love, friendship, or simply the joy of good food, check out the Valentine's Chef's Tasting Menu at the Sycamore on Fri, Feb 13, and Sat, Feb 14, 4pm-8:45pm. Make...

  • 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.

  • Valentine’s Champagne Wine Dinner at 458 West

    458 West Bed and Breakfast 458 West St, Pittsboro, NC, United States

    458 West B&B is excited to announce their Valentine's Champagne Wine Dinner on Sat, Feb 14, 6pm-9pm. The cost is $155 per person or $395 per couple, and includes dinner, a room, and...

  • Brushes and Bubbles at House of Hops

    Events at House of Hops
    House of Hops 112 Russet Run, Pittsboro, NC, United States

    Join House of Hops for Brushes and Bubbles on Sat, Feb 14, 6:30pm-8:30pm. Come paint with your love. You and yours will each paint on your pre-sketched canvas, creating a completed masterpiece...

  • Valentine’s Day with Phantom Playboys at The MOD

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

    Join The MOD for a Valentine's Day with Phantom Playboys on Sat, Feb 14, 7pm-10pm. This is one of The MOD's favorite bands and traditions. Come share the love! This event takes...

  • Watercolor Basics Workshop at The Plant

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

    Join The Plant for a Watercolor Basics Workshop on Sun, Feb 15, 12pm-4pm. This class will allow you to play and experiment with various watercolor techniques before embarking upon a...

  • Winter Art Sale at the Vineyard

    Events at FireClay Cellars
    FireClay Cellars 1276 Bowers Store Rd, Siler City, NC, United States

    Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy...

  • Grief in Motion with heart2heartnc

    Yoga Garden PBO Events
    Yoga Garden 184 East Street, Pittsboro, NC, United States

    Join Yoga Garden PBO for Grief in Motion with heart2heartnc, a unique, holistic, and body-centered workshop that explores the heartache and healing that often accompany a journey of loss and change....

  • Mead and Chocolate

    Events at The Plant
    Starrlight Mead 130 Lorax Ln, Pittsboro, NC, United States

    Bring your honey, friends, or Gal-entines for Mead and Chocolate to enjoy some chocolate paired with your tasting! $12 per person for 8 samples and two chocolates - no reservation needed!...

  • 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...

  • Live Music with Mondo Guitaro at Vino

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

    Join Vino!! Wine Shop and rebound after Valentine's Day with Live Music with Mondo Guitaro on Sun, Feb 15, 2pm-4pm. “Lonesome Tones for High Plains Drifters,” Mondo Guitaro performs spaghetti western, surf, and 1960s style instrumentals arranged for two guitars. Drink specials all day, including $7 mimosas. All tastings and events at Vino!! Wine Shop. Part of Chatham County’s...

  • Galentine’s Wreath Workshop at Buck Naked Farm

    Buck Naked Farm events
    Buck Naked Farm 1873 Chatham Church Road, Moncure, NC, United States

    Enjoy a cozy, creative February afternoon at Buck Naked Farm's Galentine's Wreath Workshop on Sun, Feb 15, 2pm-4pm. Celebrate the season of friendship with a hands-on workshop that blends herbal goodness, dried florals, and...

  • Family-Friendly Mardi Gras Celebration

    Camp Royall 250 Bill Ash Road, Moncure, NC, United States

    Let the good times roll with Chatham Pride Alliance at their Family-Friendly Mardi Gras Celebration hosted on Sun, Feb 15, 3pm-6pm at Camp Royall in Moncure, NC. Get ready for a vibrant afternoon...

  • Euchre Mondays at bmc

    Events at The Plant
    bmc brewing 213 Lorax Lane, Pittsboro, NC, United States

    Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. No experience is needed. Monday is also $5 pint night at bmc brewing. This event is free and takes...

  • St. Patrick’s Day Celebration 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 a St. Patrick's Day Celebration on Sat, Mar 14, 12pm-11pm and Tue, Mar 17, 11am-11pm in downtown Pittsboro. Celebrate St. Patrick's Day at your...

  • Fearrington Farmers Market

    Events at Fearrington Village
    Fearrington Village 2000 Fearrington Village Center, 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...

  • Mardi Gras Supper Club at The City Tap

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

    Join The City Tap for a special Mardi Gras Supper Club on Tue, Feb 17, 4pm-9pm. Celebrate Fat Tuesday with Gumbo and King Cake! This event takes place at The City...