Live Piano Music at The Sycamore
2025-09-09 18:00 - 21:00, 2025-09-11 18:00 - 21:00, 2025-09-12 18:00 - 21:00, 2025-09-13 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.

Pub Trivia at Doherty's
2025-09-09 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
2025-09-09 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.

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. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at House of Hops
2025-09-10 18:00 - 20:00 | North Carolina
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.

Open Mic Nights at NC Arts Incubator
2025-09-10 18:00 - 20:00 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
Join the NC Arts Incubator for Open Mic Nights hosted every second Wednesday, 6pm-8pm. Music, poetry, and spoken-word works are encouraged. Sign-up opens at 5:30pm. Next door, The Chatham Rabbit will be open and selling coffee.
See more events hosted by the NC Arts Incubator.

Jazz Nights at The Sycamore
2025-09-10 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.

Karaoke at Hops and Berry
2025-09-10 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. 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 all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Hoppin’ John Fiddlers’ Convention
2025-09-11 - 2025-09-13 | Shakori Hills, 1439 Henderson Tanyard Rd, Pittsboro, NC, 27312, United States
Looking forward to beautiful early fall days at the Annual Hoppin’ John Fiddlers’ Convention Thu, Sep 11-Sat, Sep 13! Planning has begun, and they are working to bring you another great year of the unique blend of old-time fiddlers’ conventions and traditional music festival that has become Hoppin’ John. Tickets go on sale Sun, Jun 15, 2025. Rates for weekend and single-day admission, as well as camping, can be found here.
Details for this year’s festival are TBD, but there are always workshops, showcases, dances, contests (including the Hoppin’ John Cook-Off), family activities, and, of course, great music! Hosted annually at the Shakori Hills Community Arts Center.
PETS
Bringing your dog to Hoppin’ John is highly discouraged. However, your furry friends are allowed if they are contained on a leash at all times. You must pay the dog admission price ($10) for each dog. They reserve the right to ask you and your dog to leave if he or she is behaving badly or they are not leashed/contained. You must clean up after your dog. Dogs over 20 pounds may not venture from your campsite.

Meds Instead of Meds
2025-09-11 12:00 - 13:30 | Chatham County Agriculture & Conference Center, 1192 US-64 W, Pittsboro, NC, 27312, United States
Meds Instead of Meds is a six-week series taught by Chatham County Cooperative Extension exploring the Mediterranean healthy eating style. Eating like those in the Mediterranean region has been shown to promote health and decrease the risk of many chronic diseases. The Mediterranean-style eating pattern incorporates the fundamentals of healthy eating that are traditionally practiced in countries bordering the Mediterranean Sea. The in-person series includes cooking demonstrations and taste tests!
Classes occur every Thursday, Sep 4-Oct 9, 12pm-1:30pm in the Cooperative Extension wing of the Chatham County Agriculture & Conference Center. Free parking is available at the venue.
See more events at CCACC.

Run Club at Thirsty Skull PBO
2025-09-11 17:00 - 18:30 | 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.

Music at Roost Beer Garden
2025-09-11 17:00 - 19:00, 2025-09-12 17:00 - 19:00 | Fearrington Village, 2000 Fearrington Village Center, Pittsboro, NC, 27312, 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 (4pm-7pm). 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 Thursdays and Fridays, 5pm-7pm. Please double-check their website to confirm – events are moved indoors or postponed during some weather conditions impacting outdoor music and activities.
MENU – WOOD-FIRED PIZZAS
Red

Mozzarella…Fresh Mozzarella, Micro Basil
Pepperoni…Mozzarella, Sauce
Prosciutto…Prosciutto, Green Olives
Carne…Housemade Sausage, Soppressata, Pepper Jam, Asiago, Croutons

White

Mushroom Carbonara…Wild Mushrooms, Pancetta, Caramelized Onions, Confit Garlic, Egg Yolk, Truffle Oil
Six Cheese Pizza…Mozzarella, Fontina, Rosemary Ricotta, Parmesan, Provolone, Pecorino

Wine Class – A View of the Finger Lakes
2025-09-11 18:00 - 19:00 | Fearrington House Restaurant, 230 Market Street, Pittsboro, 27312, United States
Join Fearrington Village for Wine Class – A View of the Finger Lakes on Thu, Sep 11, 6pm-7pm. Fall is fast approaching, and Fearrington has the perfect region to get you ready for the season! Join Wine Director Troy Revell for a focus on the beautiful Finger Lakes of upstate New York. One of the most celebrated and distinctive wine-growing areas in the eastern United States, the Finger Lakes in Autumn transform as the lakes mirror the changing leaves, creating a perfect harvest setting for winemaking. You will explore a variety of examples, including sparkling wines, Riesling, Pinot Noir, and more!
A few small bites from Chef Gagne are included, and wines tasted will be available for purchase at the end of the event. The class will take place on the Terrace behind The Fearrington House Restaurant.
This $75 all-inclusive wine class is non-refundable. If your plans have changed, please feel free to send a lucky friend in your place! Just send Fearrington an email with their name or have them bring your confirmation email.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Opinionation Trivia at House of Hops
2025-09-11 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.

Weekly Free Tastings at Vino!! Wine Shop
2025-09-12 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.

For Friday's Sake
2025-09-12 17:00 - 19:30 | For Garden’s Sake, 9197 Hwy 751 S, Durham, NC, 27713, United States
Need more time to shop? Well, you’re in luck because For Garden’s Sake extends its garden center hours during For Friday’s Sake, hosted on select every Friday evening in September, 5pm-7:30pm. The Potting Shed is open and serves beverages and Sunset Slush. Come and enjoy live music, food trucks, drinks, sweet treats, and the ambiance on the patio, taking in the sunset. Plus, get ready for fall by shopping seasonal items like pumpkins and mums.
Don’t forget to bring lawn chairs or a blanket for seating – patio tables go fast! Admission is free, so bring your family, friends, neighbors, and coworkers and enjoy the evening… For Friday’s Sake! Please check their calendar for the most up-to-date information on For Friday’s Sake events. The upcoming schedule of events is as follows:

Fri, Sep 5, 5pm-7:30pm Live Music with Sterling Scott
Fri, Sep 12, 5pm-7:30pm Live Music with Relay Relay
Fri, Sep 19, 5pm-7:30pm Live Music with Josh Branch
Fri, Sep 26, 5pm-7:30pm Live Music with Sterling Scott

Please note: For Garden’s Sake does not permit outside alcoholic beverages. They have a variety of drinks available at the Potting Shed. This free event takes place outdoors. Free parking is available on-site. See more events at For Garden’s Sake.

Run and Roam Fridays at The Plant
2025-09-12 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.

QDR Homegrown Country Music Series at MOSAIC
2025-09-12 19:00 - 21:00 | Philip H. Kohl MOSAIC Family Commons, 457 Freedom Parkway, Pittsboro, NC, 27312, United States
Two-step into the night at the QDR Homegrown Country Music Series at MOSAIC, powered by Brightspeed! Saddle up at the Tommy Edwards Stage at the Philip H. Kohl MOSAIC Family Commons. This bash is a dream come true for country music lovers and line-dancing aficionados, thanks to 94.7 QDR – your go-to for “Today’s Best Country!” Throw on those cowboy boots and join MOSAIC at Chatham Park for two-stepping to classic country jams!
The lawn opens at 6pm and the concert begins at 7pm. This event is FREE and open to the public, but registration is required. See the full schedule below and find your link to register:

Fri, Sep 12, 7pm-9pm Riggsbee Road, Register.
Fri, Sep 26, 7pm-9pm Jordan Pickett, Register.
Fri, Oct 10, 7pm-9pm Paige King Johnson, Register.
Fri, Oct 24, 7pm-9pm Clayton Blackman, Register.

Anticipate bag checks and security screenings upon entry. Food or beverages purchased outside MOSAIC, weapons, and illegal substances are prohibited. Food and beverages will be available onsite for purchase – be prepared to present your receipt to event security. Bring a lawn chair or a blanket. Pets are welcome. This event is held outdoors on the Philip H. Kohl MOSAIC Family Commons. See more events hosted by MOSAIC at Chatham Park.

Come Out and Play Sculpture Show
2025-09-13 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!

Live Music: Lee Gildersleeve & The Bad Dogs Blues Band
2025-09-13 17:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Lee Gildersleeve & The Bad Dogs Blues Band. Performances take place on the following dates:

Sun, Jun 15, 1pm-4pm.
Sat, Sep 13, 5pm-8pm.
Sun, Nov 16, 2pm-5pm.

Lee Gildersleeve was in the first wave of young blues rock guitarists that emerged in the 1960s’ blues revival. In over four decades of performing, Lee’s guitar playing has been featured with rock and roll legends Chuck Berry and Bo Diddley, rocker George Thorogood, rockabilly icon Sleepy La Beef, blues divas Koko Taylor and Marcia Ball, L.A. legend Stacy Robin, and scores of talents from coast to coast. His current band, the Bad Dogs, covers a wide range of material from Lowell Fulsom, Bo Diddley, Little Richard, Muddy Waters, and Rufus Thomas, along with many of his own original numbers. Jordan Lawrence of The Independent recently wrote, “If you’re looking for a lesson in how the blues first bled into rock ‘n’ roll, you’ll find a living demonstration in singer-guitarist Lee Gildersleeve.” As Bo Diddley said of Lee, “He gets it.” And you will too.
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.

Carolina Brewery Fall Music Series
2025-09-13 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.

The Graveyard Shift at The MOD
2025-09-13 20:00 - 23:59 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for The Graveyard Shift, a monthly dark disco dance party. All are welcome. This event is for ages 21+ and the cover is $5 per person. Upcoming event dates and guest DJs are listed below:

Sat, Jun 28, 8pm-12am Mouse the DJ.
Fri, Jul 18, 8pm-12am Guest DJ [SIN]APTIK.
Sat, Aug 16, 8pm-12am Guest DJ Ninjaficator.
Sat, Sep 13, 8pm-12am Guest DJ Baronovva.
Fri, Oct 31, 8pm-12am Guest DJ Lady Attercop.
Sat, Nov 22, 8pm-12am Mouse the DJ.
Sat, Dec 20, 8pm-12am Guest DJ That Darling DJ Duo.

See more events at The MOD.

Live Music: The Solutions
2025-09-14 12:00 - 15:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with The Solutions on Sun, Sep 14, 12pm-3pm. The Solutions is a band from RTP that plays well-known covers from the 60s, 70s, 80s, and more modern hits. They are a diverse and inclusive band that plays something for everyone, of all styles. They’ve been playing for several years at local venues and festivals. Find them on Instagram as “@TheSolutionsBand”.
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.

18th Annual PepperFest
2025-09-14 12:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
The Plant presents the 18th Annual PepperFest on Sun, Sep 14, 12pm-6pm. PepperFest is a celebration of sustainable agriculture, local farmers, and the creativity of the Piedmont’s top chefs, brewers, and artisans. The event features peppers grown on-site in the Pepper Patch, a hot sauce contest, a variety of Pepper-Themed food and drinks from The Plant denizens, a chili cook-off, pop-up vendors, live music, and many more pepper-related activities. The average distance traveled by this year’s peppers can be measured as roughly fifty yards.
PepperFest originated in Pittsboro in 2007 to support Doug Jones’s plant breeding work at Piedmont Biofarm. At the first PepperFest, visitors walked through a tent filled with raw pepper samples and filled out surveys on clipboards before they could receive a beer. Doug was licensing his seeds to seed companies, and he needed consumer data to back up his work in pepper genetics.

Touch the pepper patch and physically see the difference between a poblano and a Marconi pepper on the vine. You’ll also see the Scotch Bonnets (Jamaica’s national pepper) before they are picked for dishes served at Kingston 99 Kitchen. You’ll also see how Flying Pepper Vodka is made at Fair Game Beverage Company, using Aji Dulce Tobago peppers grown in The Plant’s pepper patch.
Grab a pepper beer from bmc brewing, food at Kingston 99 Kitchen or JDub’s PoBoys, and wander The Plant’s eclectic campus.
This event is free to the public, and tickets are not required for this year’s event. If you have accessibility questions, contact tami.schwerin@gmail.com. Pets are not recommended – please leave your furry friends at home.

Scratch-Made Italian Wine Dinner at Vino
2025-09-14 18:00 - 20:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for a Scratch-Made Italian Wine Dinner on Sun, Sep 14, 6pm-8pm, featuring the cooking of Chef Loraine Altomare (“Chef Rainey”). Chef Rainey specializes in Italian cuisine and makes all of her own pasta. She trained at Le Cordon Bleu and has worked in numerous Italian restaurants in Italy, as well as California and North Carolina. If you are interested in a four-course, authentic, scratch-made Italian dinner, paired with all Italian wines presented by Sommelier Michael Maller of Orsini Wines, then this is the dinner for you!
The cost per person is $100 (all-inclusive, including tax and gratuity), and only 32 spots remain. Please call 919.542.3922 or email anna@vinowineshopnc.com to make your reservations. Reservations must be made by Wed, Sep 10, at 3pm. Credit card information must be provided to hold the reservation. There will be no refunds for cancellations after Thu, Sep 14.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Euchre Mondays at bmc
2025-09-15 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. No experience is needed. Monday is also $5 pint night at bmc brewing.
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.
