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  • Jazz Nights at The Sycamore

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

    Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and...

  • Acoustic Trad Irish Music Seisiún

    Events at Doherty’s
    Doherty's Irish Pub and Restaurant 56 Sanford Road, Pittsboro, NC, United States

    Join Doherty's Irish Pub & Restaurant for an Acoustic Trad Irish Music Seisiún on the last Wednesday of every month, 6pm-9pm. Whether you're just beginning your music journey, a seasoned pro, or just love to listen, bring your instruments and passion for Irish music for an evening of lively tunes and great company. Musicians will be upstairs....

  • Karaoke at Hops and Berry

    Karaoke at Hops and Berry
    Hops & Berry 120 Mosaic Blvd, Suite 100, Pittsboro, NC, United States

    Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. The taproom's weekly Karaoke night turns its live-entertainment stage over to the crowd, where regulars and first-timers alike line up to belt out their favorites—whether that's a power ballad, a crowd-singalong anthem, or a deep cut only you remember. With a supportive, come-as-you-are vibe,...

  • Chatham Yardbirds vs Carolina Yankees

    Chatham County Yardbirds
    Paul Braxton Park 111 S 3rd Avenue, Siler City, United States

    Come out for a night of baseball and watch Chatham Yardbirds vs Carolina Yankees at the new Chatham Yardbirds field in Paul Braxton Park on the following dates: Wed, May 27, 7pm-10pm First Home Game of the Season! Fri, Jun 12, 7pm-10pm. Gates typically open about an hour before first pitch. The team plays an Old North State...

  • Pittsboro Farmers Market

    Farmers Markets
    Pittsboro Pop-Up Park West Salisbury Street, Pittsboro, North Carolina, United States

    The Pittsboro Farmers Market is open year-round and features select items from within a 50-mile radius. They are open every Thursday, 3pm-6pm at Pittsboro's Pop-Up Park. The product-only market features baked goods, eggs, flowers, honey, jams/jellies, soaps, plants, poultry, and other meats. Vendors include Celebrity Dairy, In Good Heart Farm, and Vortex Roasters. Many chefs...

  • Run Club at Thirsty Skull PBO

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

    Join Thirsty Skull Brewing - Pittsboro every Thursday, 5pm-6:30pm for Run Club. See all events at Thirsty Skull Brewing - PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

  • Live Music at Galloway’s

    Events at Fearrington Village
    The Belted Goat Market Street, Pittsboro, North Carolina, United States

    Visit The Belted Goat/Galloway's Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesdays, Thursdays, and Saturdays, 5pm-7pm. Check out their events calendar to see who's playing. Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.  

  • Poetry at The Plant: On The Road to Climate Action Day

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

    Come out for a special edition of Poetry at The Plant: On The Road to Climate Action Day on Thu, May 28, 6pm-7pm, in collaboration with the Haw River Assembly for The Plant's Climate Solutions Fair. Featured poets include Andrew Taylor-Troutman, Benjamin Manifold, Mick Hammer, Keith Megginson, Sheila Kannappan, and Billie Hinton. Please email [email protected] if you...

  • Beer and Banjos at Old Mill Farm

    Old Mill Farm events
    Old Mill Farm 8913 NC-751, Durham, United States

    Join Old Mill Farm for Beer and Banjos, hosted every Thursday, April-November, 6pm-8pm. This free weekly bluegrass night offers a low-key Thursday evening on the lawn with live music from local and regional acts, a rotating food truck for dinner, and the farm's full bar pouring local craft beer, cider, wine, and mead. Pet a goat, claim...

  • 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.

  • Peter Michael Wine Dinner

    Events at Fearrington Village
    Fearrington House Restaurant 230 Market Street, Pittsboro, United States

    Reserve your spot for Fearrington's Peter Michael Wine Dinner on Thu, May 28, 6:30pm-9pm. Fearrington is delighted to welcome Paul and Emily Michael, 2nd-generation owners of Peter Michael Winery in Sonoma, California. Chef Paul Gagne’s 5-course dinner menu will be paired with these eight memorable wines. This $275 wine dinner is non-refundable and totals $355 with tax...

  • Blues Jam at The MOD

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

    Join The MOD for Blues Jam hosted every Thursday, 7pm-10pm by Lo Taylor. This open jam is an excellent opportunity for those who share a love for the blues and wish to share their talents. Mr. Taylor and his band of talented musicians will make you feel right at home on our stage. Bring your voice, bring...

  • Free Public Domain Movie Night at bmc

    Free Public Domain Movie Night at bmc
    bmc brewing 213 Lorax Lane, Pittsboro, NC, United States +1 more

    Join bmc brewing for a Free Public Domain Movie Night hosted every Thursday, 7pm-10pm. Films enter the public domain in the United States when their copyright protection expires, which typically happens 95 years after publication for older works, or if owners fail to follow registration and renewal requirements. As of 2026, all films released before 1930 are...

  • Coffee with CORE

    Events with CORE
    Chatham Community Library 197 NC Hwy 87 N, Pittsboro, NC, United States

    Community Organizing for Racial Equity (CORE) welcomes you to Coffee with CORE on Fri, May 29, 9:30am-11am at Chatham Community Library in Pittsboro. Coffee with CORE is a monthly gathering where the community comes together to talk about what's happening at CORE and around us. Enjoy a cup of coffee and learn about CORE's work, connect with...

  • Luncheon at Vino!!

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

    Vino!! Wine Shop's next in-shop Luncheon is on Fri, May 29, 12pm-1pm. Chef Robin Hamilton will serve up a timeless picnic luncheon inspired by Memorial Day favorites ~ sausage (sauerkraut + mustard), Baked Beans, and Broccoli Salad! If you just want the lunch and not the wine, no problem; they have that option as well....

  • Briar Chapel Farmers Market

    Briar Chapel Farmers Market
    Great Meadow Park 161 Salt Cedar Lane, Chapel Hill, NC, United States

    Briar Chapel Farmers Market is a recent endeavor, established at the beginning of 2023. Come to the Green of Great Meadow Park every Friday, Mar-Dec, 4pm-6pm! Shoppers will find fresh seasonal produce, pasture-raised meats, native plants, local honey, baked goods, and prepared foods, much of which is harvested or made in the surrounding region. Familiar...

  • Fridays at The Farm

    Old Mill Farm events
    Old Mill Farm 8913 NC-751, Durham, United States

    Join Old Mill Farm for Fridays at The Farm, hosted every Friday night, March-November, 4pm-9pm. Enjoy family-friendly live music and activities on their quaint Century Farm. Grab a Season Pass while they are still available to gain access to all 2026 shows! Gates open at 4pm, and live music starts at 9pm. The event features a rotating selection...

  • Music at Roost Beer Garden

    Events at Fearrington Village
    Roost Beer Garden 270 Market Street, Pittsboro, United States

    Visit Roost Beer Garden at Fearrington Village, a seasonal beer garden, for live music on the porch, local beer on tap, wine by the glass, and artisan wood-fired pizza. Pull up a chair around the water fountain or under large oaks, and enjoy good weather and good company. Music is typically hosted April-October on Fridays,...

  • Weekly Wine Tasting

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

    Weekly tastings at Vino!! Wine Shop are hosted every Friday. Experts share their picks of wines with varied pricing and from diverse locations. Tasting details, including which wines will be served, are shared on their Facebook Page and in their newsletters. All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns...

  • 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.