Run Club at Thirsty Skull PBO
2025-09-18 17:00 - 18:30 (America/New_York) | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, 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.

Opinionation Trivia at House of Hops
2025-09-18 18:00 - 20:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops every Thursday, 6pm-8pm for Opinionation Trivia. This Family Fued-style trivia game is so much fun! Play at 6pm and again at 7pm for two chances to win $15 or $25 House of Hops gift cards. Bring the crew, bring food from neighbors Cafe Root Cellar or Mi Cancun, and enjoy!
More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Piano Music at The Sycamore
2025-09-18 18:00 - 21:00, 2025-09-19 18:00 - 21:00, 2025-09-20 18:00 - 21:00, 2025-09-23 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.

Pittsboro Sculpture Show
2025-09-19 - 2025-10-19 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
The first-annual Pittsboro Sculpture Celebration is a vibrant event that brings together art, creativity, and community, showcasing incredible sculptures that inspire and enrich our town. The Plant is seeking talented sculptors from NC and beyond to showcase their work and contribute to this exciting event. This is an excellent opportunity to gain exposure and connect with fellow artists and art enthusiasts in the community. Don’t miss your chance to be part of this celebration of creativity! This year’s reception will occur Fri, Sep 19-Sat, Sep 20, 2025, with sculptures on display until Sun, Oct 19, 2025.
FEATURED ARTISTS

Julio Alberdi.
William Moore.
Myles D Wilder.
Wayne Vaughn.
Kevin Vanek.
Anju Tumuluri.
Sam Spiczka.
Hamidou Sissoko.
Wendy Marshall Scott.
Joseph Sand.
Ryan Rakouskas.
José Pereira, JP.
Jason Morris.
James Malecky.
Macy James.
Frank Hiffernan.
Jeff Ganiere.
John Flack.
Holly Felice.
Lawrence Feir.
Kevin Eichner.
Mark Elliott.
Nailah Brewer.
Carol Brainard.
Viktoria Banovic.
Theresa Arico.
Joseph Bigley III.

The Sculpture Preshow and Welcome Dinner takes place Fri, Sep 19, 6pm-8pm, featuring a delicious menu catered by Kingston 99 Kitchen and Fair Game Beverage Company, as well as live music. It’s an excellent opportunity for art patrons, community members, and artists to connect in an intimate and inspiring setting. The cost is $80 per person. Purchase your tickets in advance.
The Pittsboro Sculpture Celebration will be held the following day on Sat, Sep 20, 12pm-6pm. This FREE event takes place outdoors. In addition to the beautiful sculptures on display, there will be pop-up arts and crafts vendors, live music, food, and beverages. Following the opening weekend and celebration, the sculptures will be on display for the public to see until Sun, Oct 19, 2025.
The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed pets are allowed. See all events at The Plant.

Weekly Free Tastings at Vino!! Wine Shop
2025-09-19 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.

3rd Friday Artist Receptions
2025-09-19 17:00 - 20:00 | Pittsboro Gallery of Arts, 44 Hillsboro Street, Pittsboro, NC, 27312, United States
Pittsboro Gallery of Arts is pleased to announce the return of 3rd Friday Artist Receptions. Each month, they highlight a new artist and offer an opportunity to meet them and ask about their work. Beverages and snacks will accompany. These events are held every third Friday, 5pm-8pm. Featured artists are announced on their Facebook Page.
See more Pittsboro Gallery of Arts events.

Run and Roam Fridays at The Plant
2025-09-19 17:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country Inns Trail, with local beers from bmc brewing, wines and ciders from Starrlight, spirits from Fair Game, and sake from Koshu. Local dining available at Kingston 99 Kitchen and Ta Contento.
This free event takes place indoors and outdoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. See all events at The Plant.

Pittsboro Sculpture Show: Preshow and Welcome Dinner
2025-09-19 18:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
The Pittsboro Sculpture Show: Preshow and Welcome Dinner takes place Fri, Sep 19, 6pm-8pm, featuring a delicious menu catered by Kingston 99 Kitchen and Fair Game Beverage Company, as well as Live Music by the Daniel DeLorenzo Trio. It’s an excellent opportunity for art patrons, community members, and artists to connect in an intimate and inspiring setting. The cost is $80 per person + applicable taxes and service fees. Purchase your tickets in advance – the deadline to register is Sun, Sep 14. Purchase tickets here.
MENU

NC Garlic Shrimp.
NC Jerk Pork.
Carolina Gold Rice.
Farmers Market Green Salad.
Signature Vegetable Medley: squash, zucchini, bell peppers, carrots, and corn sautéed in coconut.
Chocolate chip brownie with fruit compote.
One drink ticket for local wine or beer.

PITTSBORO SCULPTURE SHOW & CELEBRATION
The first-annual Pittsboro Sculpture Show is a vibrant event that brings together art, creativity, and community, showcasing incredible sculptures that inspire and enrich our town. The Plant is seeking talented sculptors from NC and beyond to showcase their work and contribute to this exciting event. This is an excellent opportunity to gain exposure and connect with fellow artists and art enthusiasts in the community. Don’t miss your chance to be part of this celebration of creativity! This year’s reception will occur Fri, Sep 19-Sat, Sep 20, 2025, with sculptures on display until Sun, Oct 19, 2025.
The Pittsboro Sculpture Celebration will be held the following day on Sat, Sep 20, 12pm-6pm. This FREE event takes place outdoors. In addition to the beautiful sculptures on display, there will be pop-up arts and crafts vendors, live music, food, and beverages. Following the opening weekend and celebration, the sculptures will be on display for the public to see until Sun, Oct 19, 2025.
The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed pets are allowed. See all events at The Plant.

Karaoke at Thirsty Skull
2025-09-19 19:00 - 21:00 | Thirsty Skull Brewing, 915 N Second Ave, Siler City, NC, 27344, United States
Join Thirsty Skull Brewing – Siler City on the third Friday of each month, 7pm-9pm for Karaoke with JV Jams.
See all events at Thirsty Skull Brewing. Part of the Chatham County Craft Beverages & Country Inns Trail.

Petal and Past at Reclamation
2025-09-20 12:00 - 16:00 | Reclamation, 102 Hillsboro St, Pittsboro, NC, 27312, United States
Join Reclamation for Petal and Past, your new favorite summer pop-up series! Reclamation is teaming up with Bradley Blue Vintage and Lion Hearts Homestead to bring you an eclectic, feel-good shopping experience featuring:

Vintage housewares from Reclamation, your amazing local host!
Mindfully curated clothing and trinkets from Bradley Blue Vintage.
Herbal sprays, floral bouquets, and body products from Lion Hearts Homestead.
Plus, rotating guest vendors throughout the season.

Events take place on the following dates:

Sat, Aug 16, 12pm-4pm.
Sat, Sep 20, 12pm-4pm.
Sat, Oct 18, 12pm-4pm.

Mark your calendar, bring a friend, and come see what’s blooming!

Pittsboro Sculpture Show Celebration
2025-09-20 12:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
The Pittsboro Sculpture Show Celebration will be held the following day on Sat, Sep 20, 12pm-6pm. This FREE event takes place outdoors. In addition to the beautiful sculptures on display, there will be pop-up arts and crafts vendors, live music, food, and beverages. Following the opening weekend and celebration, the sculptures will be on display for the public to see until Sun, Oct 19, 2025.
PITTSBORO SCULPTURE SHOW & CELEBRATION
The first-annual Pittsboro Sculpture Show is a vibrant event that brings together art, creativity, and community, showcasing incredible sculptures that inspire and enrich our town. The Plant is seeking talented sculptors from NC and beyond to showcase their work and contribute to this exciting event. This is an excellent opportunity to gain exposure and connect with fellow artists and art enthusiasts in the community. Don’t miss your chance to be part of this celebration of creativity! This year’s reception will occur Fri, Sep 19-Sat, Sep 20, 2025, with sculptures on display until Sun, Oct 19, 2025. Purchase your tickets to the preshow and welcome dinner.
FEATURED ARTISTS

Julio Alberdi.
William Moore.
Myles D Wilder.
Wayne Vaughn.
Kevin Vanek.
Anju Tumuluri.
Sam Spiczka.
Hamidou Sissoko.
Wendy Marshall Scott.
Joseph Sand.
Ryan Rakouskas.
José Pereira, JP.
Jason Morris.
James Malecky.
Macy James.
Frank Hiffernan.
Jeff Ganiere.
John Flack.
Holly Felice.
Lawrence Feir.
Kevin Eichner.
Mark Elliott.
Nailah Brewer.
Carol Brainard.
Viktoria Banovic.
Theresa Arico.
Joseph Bigley III.

The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed pets are allowed. See all events at The Plant.

Come Out and Play Sculpture Show
2025-09-20 12:00 - 20:00 | JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312, United States
Dozens of artists, creating in a myriad of media, are represented in this annual Come Out and Play Sculpture Show, now in its 24th year. The event takes place on a 17-acre homestead and is a gift from hosts to guests and artists. Artists do not pay a participation fee and keep all proceeds from their sales (many of the works on display are for sale). There are some out-of-state artists, but most are local to North Carolina. Each reception is filled with fantastic art and local vendors, free food and drink from the artists and hosts, visits with the horses and pigs, and live music from the North Carolina Songwriters Co-op.
The opening reception for 2025 is Sat, Aug 23 and Sun, Aug 24, 12pm until dark. Additional receptions are hosted on the following Saturdays: Aug 30, Sep 6, Sep 13, and Sep 20, 12pm until dark. Events are free. This event is family-friendly and pet-friendly (please keep all dogs on a leash). For more information, contact Debbie Meyer at writetoeloise@gmail.com or 919.357.6142.
DIRECTIONS AND PARKING
Location: JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312.
Find Your Way With #w3w: ///lizard.exhausting.profuse.
Parking Directions: Come down Wild Horse Run to the end. Please do not park on this road. On the right-hand side, go through the wooden gates and park on the right lawn. In the event that the right lawn is full, folds will be there to guide you to parking on the left. There is plenty of parking, so please follow their guidance and do not block any roads going in or out.
ACCESSIBILITY INFORMATION
The farm is not paved but there are gravel and grass areas. Parts of the property can be navigated with care for those with walkers or wheelchairs, including the outdoor area where tents are set up and where the musicians perform. Many individuals with walkers and wheelchairs, including the artists themselves, attend the event every year. Please contact the event organizer for additional accessibility questions.

THE HISTORY BEHIND THE EVENT
The Come Out and Play Sculpture Show began in 2002 to commemorate the first anniversary of 9/11 and has continued since then to promote kindness in the world through art and by connecting people. Debbie Meyer and her husband, Eric Brantley, coordinate and host this amazing show each year; it is truly a rewarding gift!

Tasting Classes with EB Wines
2025-09-20 14:00 - 15:00 | EB Wines, 40140 Moring, Chapel Hill, 27517, United States
The seventh annual Wine Tasting Classes is a collection of monthly wine tasting classes hosted by Esteban Brunello, owner of EB Wines. The classes are informative yet relaxed and open to guests with varying levels of knowledge, from novice wine drinkers to seasoned tasters. Classes are led by owner and wine director Esteban Brunello, who guides guests through the wine tasting process. Guests will learn to identify various wine notes, discover techniques in the winemaking process, and receive recommendations for food pairings.
Mark your calendars for the following class dates:

Sat, Jul 26, 2pm-3pm Refreshing Whites.
Sat, Aug 23, 2pm-3pm Skin Contact.
Sat, Sep 20, 2pm-3pm Domestic Wines.
Sat, Oct 18, 2pm-3pm Obscure Reds.
Sat, Nov 15, 2pm-3pm Fall Reds.
Sat, Dec 13, 2pm-3pm Sparking – Petillant Naturel.

EB Wines is part of the Chatham County Craft Beverages & Country Inns Trail. See all events at EB Wines.

2025 Festejo Celebration
2025-09-20 14:00 - 18:00 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
Celebrate Hispanic Heritage Month with The Hispanic Liaison during their 2025 Festejo Celebration on Sat, Sep 20, 2pm-6pm at the NC Arts Incubator. Festivities include live music and performances, delicious food, art exhibits, a piñata, dance lessons, face painting, raffle prizes, and more. Admission is free and everyone is welcome.
See more events hosted by the NC Arts Incubator.

Carolina Brewery Fall Music Series
2025-09-20 17:30 - 20:00 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Take in live music from local musicians on the patio at Carolina Brewery and Grill during their Fall Music Series. Hosted Saturdays, September-October, 5:30pm-8pm. See specific dates and performers listed below.

Sat, Sep 6, 5:30pm-8pm Deep Chatham Ramblers.
Sat, Sep 13, 5:30pm-8pm ZamBamBoogee.
Sat, Sep 20, 5:30pm-8pm Vinnie’s Garage Band.
Sat, Sep 27, 5:30pm-8pm The 8:59’s.
Sat, Oct 4, 5:30pm-8pm Mondo Guitaro.
Sat, Oct 11, 5:30pm-8pm Big T.
Sat, Oct 18, 5:30pm-8pm Jason Damico.
Sat, Oct 25, 5:30pm-8pm Colby Jack and The High Lifes.

Admission is free. Enjoy burgers, tacos, apps, and of course, their award-winning beer. Their Oktoberfest Menu is available Tue, Sep 16-Tue, Sep 30. Part of the Chatham County Craft Beverages and Country Inns Trail. See all events at Carolina Brewery & Grill.

Live Music: D.W. & The Spirit Kings at Havoc
2025-09-20 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with D.W. & The Spirit Kings on Sat, Sep 20, 6pm-9pm. ThiccBurger food truck will be onsite at Havoc 5pm-9pm.
This event is free and takes place outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Southern Storytelling by Roger Valente
2025-09-21 17:00 - 19:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for Southern Storytelling by Roger Valente on Sun, Sep 21, 5pm-7pm. Come on over and sit a spell for an entertaining evening of North Carolina tales. This Sunday Social event is open to adults only. Please RSVP by contacting sue@fireclaycellars.com.
FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Euchre Mondays at bmc
2025-09-22 18:00 - 20:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
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 doubles as $5 pint night at bmc brewing, so you can pair your hand of cards with one of the 18 beers bmc brews on site, alongside hard cider, hard seltzer, wine, and non-alcoholic options.
The event is free and takes place indoors. The space is wheelchair accessible, and on-site parking is free. Pets are not permitted indoors at bmc brewing. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Fearrington Farmers Market
2025-09-23 15:00 - 17:00 | Fearrington Farmers Market, E Camden, 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.

Run Club at House of Hops
2025-09-23 18:00 - 20:00 | NC
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.

Music Bingo at Hops and Berry
2025-09-23 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, 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 buffs.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Pub Trivia at Doherty's
2025-09-23 19:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, 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.

Blues Jam at The MOD
2025-09-23 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 Tuesday, 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.

Music Bingo at House of Hops
2025-09-24 18:00 - 20:00 | NC
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.

Jazz Nights at The Sycamore
2025-09-24 18:00 - 21:00 | 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.

Acoustic Irish Music Seisiún
2025-09-24 18:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for an Acoustic 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.
See more events at Doherty’s.

Karaoke at Hops and Berry
2025-09-24 19:00 - 22:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, 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, it’s as fun to cheer from a table as it is to step up and perform.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.
