Jazz Nights at The Sycamore
2030-08-14 18:00 - 21:00, 2030-08-21 18:00 - 21:00 (America/New_York) | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, 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 the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Pittsboro Farmers Market
2030-08-15 15:00 - 18:00, 2030-08-22 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, 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, under the solar panels at The Plant. 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 at restaurants in our area network with Pittsboro Farmers Market vendors, including Kingston 99 Kitchen and West End Kitchen & Catering. You can find a complete, up-to-date list of vendors here.
Special markets are hosted on occasion.
The Pittsboro Farmers Market takes place outdoors, rain or shine. Leashed, well-behaved pets are allowed. Entry is free. Bringing your own bags, cash, and a cooler for perishable items is advised. The market is held on a gravel lot beneath the solar panels, with free parking available nearby. See more events at The Plant. See more farmers markets in our area.

Live Music at Galloway's
2030-08-15 17:00 - 19:00, 2030-08-16 17:00 - 19:00, 2030-08-17 17:00 - 19:00, 2030-08-21 17:00 - 19:00, 2030-08-22 17:00 - 19:00, 2030-08-23 17:00 - 19:00, 2030-08-24 17:00 - 19:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesday-Saturday, 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.

Live Piano Music at The Sycamore
2030-08-15 18:00 - 21:00, 2030-08-16 18:00 - 21:00, 2030-08-17 18:00 - 21:00, 2030-08-20 18:00 - 21:00, 2030-08-22 18:00 - 21:00, 2030-08-23 18:00 - 21:00, 2030-08-24 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, 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.

Live Music with Mondo Guitaro at Thirsty Skull
2030-08-15 19:00 - 21:00 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro for Live Music with Mondo Guitaro, hosted every third Thursday,7pm-9pm. Come hang out and listen to the awesome sound of Mondo Guitaro. “Lonesome Tones for High Plains Drifters”: Mondo Guitaro performs spaghetti western, surf, and 1960s-style instrumentals arranged for two guitars. You won’t want to miss this!
There is no cover charge. Craft beer and glasses of wine from Thirsty Skull’s selection will be available for purchase. Ages 21 and older only.
See more events at Thirsty Skull Brewing – Pittsboro. Part of the Chatham County Craft Beverages and Country Inns Trail.

Blues Jam at The MOD
2030-08-15 19:00 - 22:00, 2030-08-22 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, 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 your instruments, or just bring your ears to partake in this musical delight. The Mod is dedicated to providing space for live music, great food, craft beverages, community, and love. Arrive early for musician sign-up or to grab a table for the evening. Any schedule changes due to weather, holidays, or unforeseen circumstances will be posted on their Facebook and Instagram pages.
See more events at The MOD.

Weekly Free Tastings at Vino!! Wine Shop
2030-08-16 17:00 - 19:00, 2030-08-23 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Weekly free 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 Trail.

Pittsboro's Finally Fridays Art Walks
2030-08-16 17:00 - 20:00 | Pittsboro, Pittsboro, NC, 27312, United States
Pittsboro’s Finally Fridays Art Walks are held every Third Friday, 5pm-8pm, in downtown Pittsboro (Hillsboro Street and Pittsboro’s Social District). This FREE, family-friendly monthly event highlights Pittsboro’s vibrant downtown and artistic community. Shops spill onto the sidewalks, creating a festive atmosphere. Community artists form Art Pods with a boho vibe. Experience Pittsboro Finally Fridays Arts Walk through the eyes of its beloved sheep mascot, who is small in stature but full of personality.
Pittsboro’s beloved “Finally Fridays Arts Walk” kicks off the new year with a special January tradition—offering a vibrant night for art enthusiasts, locals, and visitors alike. This month’s event promises more than just creative inspiration: attendees are invited to embark on a unique walking tour through Downtown Pittsboro’s Social District while enjoying a variety of inventive mocktails at the town’s charming businesses, bars, and eateries.
Start your evening as the sun sets over Pittsboro’s historic downtown. As you stroll the Social District, you’ll find participating venues each featuring their own signature non-alcoholic mocktail creations. Explore local bars, restaurants, and businesses; each stop offers a new flavor experience that reflects the town’s creative culinary spirit. Participating businesses include:

Cactus Cowgirl.
Doherty’s Irish Restaurant & Pub.
Katty Korner Downtown Market.
New Horizons.
Reclamation.
Pittsboro Gallery of Arts.
Pittsboro Toys.
The Beagle.
The City Tap.
The Mod.
Vino!! Wine Shop.
West End Kitchen & Catering.

Additionally, Aromatic Roasters will have their coffee truck set up near the Welcome Center.
The Finally Fridays Arts Walk is a great way to experience Pittsboro’s warmth and creativity during the winter. Whether you’re a regular or a first-time visitor, this event offers a welcoming atmosphere, delightful non-alcoholic beverages, and a celebration of local artistry and community spirit. Bring your friends, family, or colleagues and toast to the new year—mocktail in hand!
This FREE, family-friendly event takes place outdoors along the streets and sidewalks of downtown Pittsboro. There are no fees to participate. Downtown Pittsboro and its businesses have typical ADA accommodations. Parking is free and available within walking distance to the event. Leashed pets are encouraged. Select Downtown Pittsboro shops will remain open until 8pm for this event. See more Downtown Pittsboro events.

Free Wine Tastings at The Belted Goat
2030-08-17 13:00 - 15:00, 2030-08-24 13:00 - 15:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village for free wine tastings select Saturdays, 1pm-3pm. Tastings will vary depending on when you visit, so please check their calendar before planning your visit.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Fearrington Farmers Market
2030-08-20 15:00 - 17:00 | Fearrington Village, 2000 Fearrington Village Center, Pittsboro, NC, 27312, 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, happy living.
Fearrington Farmers Market has more than 3 dozen members and is now in its 30th season. Not all vendors are there every week, but some vendors are there every week, year-round. Each market features live music. Vendors include Celebrity Dairy, In Good Heart Farm, and bmc brewing. See their full list of vendors.
Come early if you’d like to review what is being offered; sales begin at the scheduled time, signaled by the bell. Bring along small bills ($20 or lower) to pay for your purchase. Some vendors accept credit and debit cards, and most will accept checks. This event takes place outdoors, rain or shine. Entry is free. Leashed, well-behaved pets are welcome. See more events at Fearrington Village.

Brewers Behind the Bar at bmc
2030-08-21 11:00 - 18:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join bmc brewing for Brewers Behind the Bar, hosted every first and third Wednesday, 11am-6pm. Meet the makers, taste the stories, and ask award-winning craft brewers anything.
This event is free and takes place indoors. The space is wheelchair accessible. No pets are allowed. Free parking is available on-site. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at House of Hops
2030-08-21 18:00 - 20:00
Join House of Hops every Wednesday, 6pm-8pm for Music Bingo hosted by DJ Special K. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Community Potluck Meal
2030-08-23 18:00 - 20:30 | Freedom Family Church Community Center, 421 North Holly Street, Siler City, 27344, United States
Every fourth Friday, 6pm-8:30pm, join Siler City Community Meals for a Community Potluck Meal. Gather for a meal, see old friends, and make new ones. The meal is free, and they are hoping for potluck donations as they get reorganized and understand the community’s needs moving forward. This event is rain or shine.
See more Siler City events.
