Live Piano Music at The Sycamore
2025-09-02 18:00 - 21:00, 2025-09-04 18:00 - 21:00, 2025-09-05 18:00 - 21:00, 2025-09-06 18:00 - 21:00, 2025-09-09 18:00 - 21:00 (America/New_York) | 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.

Blues Jam at The MOD
2025-09-02 19:00 - 22:00, 2025-09-09 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.

Monthly Markets at MOSAIC
2025-09-03 18:00 - 20:00 | MOSAIC at Chatham Park, 367 Freedom Parkway, Pittsboro, NC, 27312, United States
MOSAIC at Chatham Park hosts Monthly Markets every first Wednesday, Apr-Oct, 6pm-8pm. The MOSAIC Market aims to bring together a diverse array of handmade goods, artisanal creations, and farm-fresh offerings in one dynamic and engaging space. The event includes local growers and makers, craft beverage vendors, food trucks, and a special live music guest. This event is not just a market; it’s a gathering of like-minded individuals committed to quality, sustainability, and the beauty of artisanal craftsmanship.
Featured Chatham County vendors include bmc brewing, Hops & Berry Pittsboro, Havoc Brewing Company, Tacos Paraiso, and Red Moose Brewing Company. Say hello to 79° West while you’re there! At MOSAIC’s Markets, they will be hosting bands at the Works Yard Stage each night to provide additional marketing efforts and engagement from the community to create high traffic. The musical guest lineup is listed below:

Wed, Apr 2, 6pm-8pm Dorian Devins, Register.
Wed, May 7, 6pm-8pm The Jive Bombers, Register.
Wed, Jun 4, 6pm-8pm Geoff McBride, Register.
Wed, Jul 2, 6pm-8pm Daniel DeLorenzo, Register.
Wed, Aug 6, 6pm-8pm Popcorn Blue Band, Register.
Wed, Sep 3, 6pm-8pm Brown Mountain Lightning Bugs, Register.
Wed, Oct 1, 6pm-8pm Organ Failure, Register.

Monthly markets are held in The Works Yard Paeso. See more events hosted by MOSAIC at Chatham Park.

Jazz Nights at The Sycamore
2025-09-03 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.

Open Mic Night at Fair Game Beverage Company
2025-09-03 18:30 - 21:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Call all performing artists! Fair Game Beverage Company, located at The Plant in Pittsboro, hosts its Open Mic Night on the first Wednesday of every month, 6pm-9pm. Bring your talent – originals, covers, comedy, stories, or poetry! Or just come spectate and listen to local artists. Hosted by Danny Whipple.
Local NC beers, wines, ciders, and craft cocktails will be available at the bar. Local dining available at Kingston 99 Kitchen and Ta Contento. This event is free and takes place indoors. The Plant is wheelchair accessible, and additional accommodations are available upon request. Free parking is available on-site. No pets allowed, please. See more events at The Plant. See all events at Fair Game Beverage Company. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

8 Week Carolina Shag Group Series
2025-09-04 17:30 - 18:30 | Forest Hall at Chatham Mills, 480 Hillsboro Street, Suite 350, Pittsboro, NC, 27312, United States
If you love listening to Motown and Beach music, then you will love this 8 Week Carolina Shag Group Series hosted by Forest Hall at Chatham Mills and the Chatham Social Club on Thursday nights, Aug 7-Sep 25, 5:30pm-6:30pm. Make your trips to the beach this summer unforgettable by learning our state’s social dance.
The cost for the class is $285 per couple and includes 8 hours of group instruction for two people. Intermediate dancers welcome; a partner is needed for the class. Register now at chathamsocialclub.com – limited spots available! See more events at Chatham Mills.

Unisong: Guided Song Circle at NC Arts Incubator
2025-09-04 18:00 - 19:30 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
What medicine does your heart need? Join the NC Arts Incubator for Unisong: Guided Song Circle, hosted on the first Thursday of every month, 6pm-7:30pm. During this 90-minute journey designed for beginner and experienced singers alike, Unisong instructors will guide you through singing and movement that invite release, restoration, and healing of the heart.
See more events hosted by the NC Arts Incubator.

8 Week Beginner Cha Cha Series
2025-09-04 19:00 - 20:00 | Forest Hall at Chatham Mills, 480 Hillsboro Street, Suite 350, Pittsboro, NC, 27312, United States
During this 8 Week Beginner Cha Cha Series, you’ll learn a popular Latin dance that is done at weddings and holiday parties, on vacations and cruises, and more. Build your dance skills as a new dancer and learn to dance the rhythm of the Cha Cha. Hosted by Forest Hall at Chatham Mills and the Chatham Social Club on Thursday nights, Aug 7-Sep 25, 7pm-8pm.
The cost for the class is $285 per couple and includes 8 hours of group instruction for two people. No prior dance experience is required; a partner is needed for the class. Register now at chathamsocialclub.com – limited spots available! See more events at Chatham Mills.

Summer Our State Book Club Event
2025-09-04 19:00 - 21:00 | Fearrington Barn, 500 Market Street, Pittsboro, NC, 27312, United States
Join McIntyre’s Books for the Summer Our State Book Club Event on Thu, Sep 4, 7pm-9pm. Fearrington Village is delighted to host Wiley Cash for the Our State Book Club in the Fearrington Barn with special guests, fellow North Carolinians, Georgann Eubanks, Donna Campbell, and Our State Editor in Chief Elizabeth Hudson. New York Times bestselling author Wiley Cash handpicks contemporary books by fellow North Carolinian authors and those writing books set in the state, encouraging readers to join in the fun. Wiley reviews each book in both the print and digital versions of the magazine and produces two podcast episodes highlighting the selected book and author.
Wine and hors d’oeuvres will be served. Featured books are available for sale at McIntyre’s Books at a 20% discount. Bundle your Book Club choices quarterly and receive 20% off or free freight. Tickets are $50 per person. The deadline to register is Fri, Aug 29.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Flatwoods Festival
2025-09-05 - 2025-09-06 | Bennett, 52-68 W Raleigh Street, Bennett, NC, 27208, United States
The 27th Annual Flatwoods Festival on Fri, Sep 5, 5pm-8pm and Sat, Sep 6, 10am-4pm is hosted by the Tri-County Ruritan Club and celebrates a fun family experience. Festivities include an antique car, truck, tractor, a horse parade, food vendors, craft vendors, inflatable jump houses, and live music. For more information, contact Debby Hussey at husseyfarm@rtmc.net or 919.548.5129. More events in Bennett.

MERSEA - Fall 2025 Trunk Show
2025-09-05 10:00 - 17:00, 2025-09-06 10:00 - 17:00 | Dovecote Home and Garden, Nest, and Sprout, 250 Market Street, Pittsboro, NC, 27312, United States
Fri, Sep 5-Sat, Sep 6, 10am-5pm, Dovecote will host designer Ashley Stanley from MERSEA, just in time to lighten your holiday shopping load! Come out this weekend and show Ashley some love!
Dovecote Home and Garden, Nest, and Sprout in Fearrington Village hosts trunk shows that afford one-on-one time with designers and opportunities to shop beyond their store offerings. Trunk Shows give you the chance to see an entire collection, not just what they bring in for the store, which means it is the only time that some sizes and colors are available in certain styles. Chatting with a rep or designer – the experts – gives you the best insight into what styles and sizes are perfect for you, so you can be sure you’re getting pieces that you’ll treasure forever. Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.
ABOUT THE DESIGNER
MERSEA’s story began in 2013 with a singular passion in mind: travel, and the nostalgic scents that come along with it. Fascinated by the ability of scent to transport the body and soul to places old and new, this led their founders to uncover the creations of artisans found in corners around the world. Now, MERSEA is no longer exclusively a destination for scents and self-care, but a curated collection of travel essentials crafted entirely for your journey—wherever you may go.

Line Dancing Classes at Chatham Mills
2025-09-05 11:00 - 12:00 | Forest Hall at Chatham Mills, 480 Hillsboro Street, Suite 350, Pittsboro, NC, 27312, United States
Build your skills on the dance floor with Line Dancing Classes at Chatham Mills, hosted by Forest Hall at Chatham Mills and the Chatham Social Club every Friday, 11am-12pm. The cost is $25 per class, and all skill levels are welcome; no partner is needed for class. Register now at chathamsocialclub.com – limited spots available! See more events at Chatham Mills.

Run and Roam Fridays at The Plant
2025-09-05 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.

Come Out and Play Sculpture Show
2025-09-06 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!

Carolina Brewery Fall Music Series
2025-09-06 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: Cory Luetjen
2025-09-06 19:30 - 22:30 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Live Music with Cory Luetjen on Sat, Sep 6, 7:30pm-10:30pm.
This event is free and takes place indoors. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

First Sunday Sound Bath
2025-09-07 11:30 - 12:30 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
At Starrlight Mead’s First Sunday Sound Bath, cathedral-like acoustics in this space bring a sense of reverence and play to these sessions. Think of it like a non-dogmatic sonic church.
Events are hosted on the first Sunday of each month from 11:30am-12:30pm. To attend, please RSVP to liodhruna@gmail.com. An admission fee of $20 per person is recommended for this event. If you are able, please Venmo or PayPal @AncientSongTherapy, or make other arrangements (this exchange is greatly appreciated). Please bring your own yoga mat, cushions, and comfort items. For virtual attendees: Jenn will go live at 11:30am, and you can tune in any time. The event will also be available on demand after the live session for those who could not attend. Any comments or questions will be answered once the offering is done.
Starrlight Mead is part of The Plant. The space is wheelchair accessible, with parking and entry available behind the production facility. Additional free parking is available on-site. Pets are not allowed. See all events at Starrlight Mead. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

The Wanderer's Market
2025-09-07 12:00 - 16:00 | West End Kitchen and Catering, Pittsboro, North Carolina, 27312, United States
Join West End for The Wanderer’s Market hosted every first Sunday, May-Oct, 12pm-4pm. Markets include a new music guest each month, great food and drink from West End, and shopping at Finders and Seekers Emporium.
See more events at West End Kitchen and Catering.

Live Music: Colby Jack and The High Lifes
2025-09-07 15:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Colby Jack and The High Lifes on Sun, Sep 7, 3pm-5pm. Colby Jack & the High Lifes are a high-energy Vintage Honky Tonk band from Greensboro, North Carolina. Playing all your country favorites from Hank Williams to Travis Tritt, as well as their timeless originals. Grab a beer and a dance partner!
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they are in a position of having to cancel, they will try to do so well in advance. 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 pets are allowed. This event is free! See all events at The Plant.

Pittsboro End-of-Summer Fest
2025-09-07 16:00 - 20:00 | Pittsboro Pop-Up Park, West Salisbury Street, Pittsboro, North Carolina, 27312, United States
After rescheduling their annual summer celebration due to inclement weather, The Pittsboro Business Association proudly presents Pittsboro End-of-Summer Fest on Sun, Sep 7, 4pm-8pm. Enjoy all the usual Summer Fest activities, but in (hopefully) cooler temperatures. Activities typically include a Decorated Bicycle Parade, juggling, giant balloons, hula hooping, balloon animals, a duck pond for prizes, axe throwing, and fun for the whole family. There will also be food trucks and local vendors. Enjoy live music from SouLe and the Super Band and Your Mama’s New Boyfriend.
This celebration takes place at the Pittsboro Pop-Up park between Salisbury and Hanks streets in downtown Pittsboro. This venue is wheelchair accessible. Leashed pets are allowed, but discouraged.
The Chatham County Historical Association wouldn’t miss Pittsboro’s Summerfest, and you shouldn’t either! Stop by their table to say hi, and be sure to bring your own stories about Old Chatham County—they’d love to hear them! Summerfest is sponsored by the Pittsboro Business Association, and the Chatham County History Association is a proud participant.

Tap Dancing - Advanced
2025-09-08 13:00 - 14:00 | Chatham Grove Community Center, 1301 Andrews Store Road, Pittsboro, 27312, United States
Tap Dancing – Advanced is for experienced tappers who are skilled at named steps and can perform intricate choreography. Tap shoes are recommended but not required. This class occurs every Monday, Sep 8-Oct 13, 1pm-2pm. Registration opens Wed, Aug 15, and closes Mon, Sep 15.
This event is held indoors at the Chatham Grove Community Center by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). Registration is $60 per person. Ages 18+ are welcome. See more CCPRCR events.

Fearrington Farmers Market
2025-09-09 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.

Tap Dancing - Intermediate
2025-09-10 11:30 - 12:30 | Chatham Grove Community Center, 1301 Andrews Store Road, Pittsboro, 27312, United States
Tap Dancing – Intermediate is for dancers who are ready to move their feet a bit faster and learn more complex choreography. If you have completed the beginner class or have prior experience and need a refresher, this class is for you. This class occurs every Wednesday, Sep 10-Oct 15, 11:30am-12:30pm. Registration opens Wed, Aug 15, and closes Mon, Sep 15.
This event is held indoors at the Chatham Grove Community Center by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). Registration is $60 per person. Ages 18+ are welcome. See more CCPRCR events.

Poetry at The Plant
2025-09-10 18:00 - 19:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Come out for Poetry at The Plant on the second Wednesday of every month, 6pm-7pm. Enjoy an hour of original poetry from regional poets in the Fair Game Beverage Company Wheelhouse Tasting Room (and enjoy a drink and meal while you’re at it)!
Local NC beers, wines, ciders, and craft cocktails will be available at the bar. Local dining available at Kingston 99 Kitchen and Ta Contento. This event is free and takes place indoors. The Plant is wheelchair accessible, and additional accommodations are available upon request. Free parking is available on-site. No pets allowed, please. See more events at The Plant. See more events at Fair Game Beverage Company. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.
