Live Piano Music at The Sycamore
2025-10-18 18:00 - 21:00, 2025-10-21 18:00 - 21:00, 2025-10-23 18:00 - 21:00, 2025-10-24 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.

Live Music: The Cover Society at Havoc
2025-10-18 18:00 - 21:00 | Havoc Brewing Company, 39 West Street, Pittsboro, NC, 27312, United States
Havoc Brewing Company presents Live Music with The Cover Society on Sat, Oct 18 6pm-9pm. De Pana Flavors 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.

Halloween Movie Night at Bottom of the Fox Farm
2025-10-18 18:30 - 21:30 | Bottom of the Fox Farm, 157 Joe Fox Road, Siler City, 27344, United States
Join Bottom of the Fox Farm for a Halloween Movie Night on Sat, Oct 18, 6:30pm-9:30pm. Bring a blanket or chair and enjoy a showing of Hocus Pocus under the stars. Costumes are encouraged! Showtime starts at 7:30pm for this pay-what-you-can, family-friendly event. Tickets are not necessary, but they are asking guests to RSVP so they can get a head count. Pack a picnic or a cooler. Light concessions (popcorn, candy, drinks) will be available for purchase. Bouquets are available to reserve at the beginning of the night and will be ready for pick up on your way out.

Live Music with Neon Nights at The MOD
2025-10-18 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Live Music with Neon Nights on Sat, Oct 18, 7pm-10pm.
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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.

Live Music: Trash Van Fever
2025-10-18 19:30 - 21:30 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Trash Van Fever on Sat, Oct 18, 7:30pm-9:30pm.
This event takes place on the patio at The City Tap. There is no cover charge for this event, but tipping the musicians is recommended. See all events at City Tap.

Thistle & Oak Fall 2025 Trunk Show: Will Leather Goods
2025-10-19 10:00 - 17:00 | Thistle and Oak, 209 Market Street, Pittsboro, 27312, United States
Sat, Oct 18-Sun, Oct 19, 10am-5pm, Thistle and Oak will host designer Will Leather Goods as part of their Fall 2025 Trunk Show series. “Discover Your Will”. A family-owned brand from Eugene, OR, founded by Will Adler. Leather experts who embrace worldwide artisans to create products that uphold their Lifetime Guarantee. Will Leather Goods designs and crafts a range of travel bags, personal leather accessories, wallets, belts, and gifts. Offering an array of leathers and styles, this event is just the right time to create your ideal travel bag, belt, or accessory.
Thistle and Oak in Fearrington Village hosts trunk shows that offer one-on-one time with designers and provide opportunities to shop beyond their in-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.

Fall Floral and Pumpkin Workshop
2025-10-19 14:00 - 17:00 | Jordan Lake Farms, 2170 Marthas Chapel Rd, Apex, NC, 27523, United States
Join Jordan Lake Farms for a Fall Floral and Pumpkin Workshop on Sat, Oct 19, 2pm-5pm at their scenic farm, where creativity blooms! Participants will wander through vibrant fields to hand-pick their own seasonal flowers, crafting a unique autumnal arrangement. Instead of a traditional vase, you’ll use a charming pumpkin cookie jar to showcase your floral masterpiece, adding a cozy, festive touch. This workshop is perfect for a girls’ afternoon out, a special mother-daughter bonding experience, or a fun date for couples.
This class takes place at the Jordan Lake Farms Pavilion. The cost is $80 per arrangement participant and $20 for participant guest/floral helpers. The workshop includes a pumpkin-shaped cookie jar that will come in handy for the fall season, a bucket full of flowers, fall decorations, step-by-step instructions, tools, and a glass of wine. You’re welcome to bring outside food to enjoy, but there will also be mini charcuterie boards for purchase with NC products such as cheeses, salamis, cheese straws, cookies, peanuts, and much more. Participants must be at least 14 years old. Those 14-17-year-olds need to be accompanied by an adult.
Spots are limited. Reserve yours today to secure your place in this blooming adventure. Registration is non-refundable.

"Spirits of Pittsboro's Past" Walking Tour
2025-10-19 17:30 - 19:30 | Chatham County Historical Museum, 9 Hillsboro St, Pittsboro, NC, 27312, United States
Don’t miss the chance to see history come alive before your eyes at the Spirits of Pittsboro’s Past Walking Tour, hosted by the Chatham County Historical Association (CCHA), just in time for Halloween! Take a walk through downtown Pittsboro for an evening filled with local folklore and historical reenactments. The tour blends Chatham’s rich heritage with stories and legends, all presented by costumed interpreters portraying figures from the town’s past.
The journey begins at the historic courthouse and winds through old cemeteries, churches, and hidden corners, with each stop offering a window into the lives of the people and moments that shaped Pittsboro. The tour will take place on the following dates:

Sat, Oct 18, 5:30pm-7:30pm.
Sun, Oct 19, 5:30pm-7:30pm.

EVENT DETAILS

Check-in is at 5:15pm, with the tour starting promptly at 5:30pm both days.
Age Requirement: 12 years and older only (no pets or strollers).
Weather: Rain or shine (rescheduled only in case of severe weather).
This tour takes place indoors and outside, lasting between 90 and 120 minutes.
Bring a flashlight. Wear comfortable clothing and sturdy shoes.
A liability waiver will be required at check-in.
Limited to 60 participants per evening, split into three small groups for a more personal experience.
Free parking is available behind the new Chatham County Courthouse and Justice Center.
Pets are not allowed; please leave your furry friends at home.
Accessibility: Tour participants will need to be able to navigate stairs, outdoor sidewalks, and grassy areas.

Tickets are $25 for CCHA members and $30 per person for nonmembers. Space is limited. Member-only tickets go on sale Mon, Sep 1, and sales of nonmember tickets will begin Mon, Sep 15 (if there are still tickets available). Tickets are available online only. For tickets and more information, go to www.chathamhistory.org.

Sacred Sound with Garth Robertson
2025-10-19 18:00 - 19:30 | Yoga Garden, 184 East Street, Pittsboro, NC, 27312, United States
Join Yoga Garden PBO for Sacred Sound with Garth Robertson, hosted on Sun, Oct 19, 6pm-7:30pm. Garth humbly offers Sound Ceremony, a modality that combines the two for a deep and meaningful experience. Guided by instruments from around the world, each person who is present co-creates the special container that we all use as a collective pathway into our deeper selves and our collective healing. There are mats and supports available at Yoga Garden, but please feel free to bring whatever you need to be comfortable on the ground for the duration of the session, which can last over an hour. If there is anything specific you’d like support with during the session, please let Garth know before the Ceremony begins.
Some benefits of Sacred Sound include:

Reduced stress and anxiety significantly.
Lower anger and blood pressure.
Improved circulation and increased blood flow.
Deep relaxation and pain relief.
Chakra balancing.

The cost is $30 per person. See more events at Yoga Garden PBO.

Makers: Recycle, Upcycle, and Create!
2025-10-20 18:00 - 19:30 | The Arts Center, 964 East Street, Suite 105, Pittsboro, NC, 27312, United States
At Makers: Recycle, Upcycle, and Create, you’ll be challenged to combine DIY craft supplies with repurposed household discards and recyclables in generating artful expressions and upcycled decor! This four-week session takes place every Monday, Oct 6-Oct 27, 6pm-7:30pm. Registration opens Mon, Aug 18, and closes Mon, Sep 29.
This event is held indoors at the new Chatham County Parks, Recreation, and Cultural Resources (CCPRCR) Arts Center, located at 964 East Street, Suite 105, Pittsboro, NC 23712, on the backside of the building. To access the studio, drive straight through the open gate and look for the sign that reads “Arts Center”. Visual Arts participants are permitted to park in the back parking lot.
Registration is $15 per person. Ages 10+ are welcome. See more CCPRCR events.

Blues Jam at The MOD
2025-10-21 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.

Sound Unity - Music Group
2025-10-22 13:45 - 14:45 | Chatham Grove Community Center, 1301 Andrews Store Road, Pittsboro, 27312, United States
In Sound Unity – Music Group, you will experience preferred music and play with styles, instruments, and creativity through fun activities while also building on the group’s relational dynamics and personal strengths. Registrants will take home their own Hohner harmonica and Lyons kazoo. This class includes noise. Classes are held every Wednesday, Oct 8-22, 1:45pm-2:45pm. Registration opens Fri, Aug 15, and closes Wed, Oct 1.
This event is held indoors at the Chatham Grove Community Center by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). Registration is $35 per person. Ages 18+ are welcome. Participants of all abilities are welcome. See more CCPRCR events.

Jazz Nights at The Sycamore
2025-10-22 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.

Sip and Paint: Paint Your Partner at The MOD
2025-10-22 18:00 - 21:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for an evening of unadulterated creativity, great cocktails, laughter, and probably a big mess, too, at this Sip and Paint: Paint Your Partner on Wed, Oct 22, 6pm-9pm. Bring your partner, BFF, or some rando (we won’t judge) and let your paintbrush take the wheel in creating a visual masterpiece of the person behind your canvas. All supplies are provided. This event is $25 per couple and pre-registration is required. Contact them or stop by to reserve your spot. Hosted by Mod Mama Jamie Ellen herself, a long-time artist and creative.
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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.

Thistle & Oak Fall 2025 Trunk Show: DU/ER
2025-10-24 10:00 - 17:00, 2025-10-25 10:00 - 17:00 | Thistle and Oak, 209 Market Street, Pittsboro, 27312, United States
Fri, Oct 24-Sat, Oct 25, 10am-5pm, Thistle and Oak will host designer DU/ER as part of their Fall 2025 Trunk Show series. The “Look Good, Feel Good” Vancouver-based clothing line offers stylish active wear that is professional enough for everyday wear. Combines sustainable fabrics with exceptional comfort and style for everyday adventures. Clothing that enables people to move through life with ease and confidence. Try on a pair of “The World’s Most Comfortable Pants” and enter the drawing for a free pair.
Thistle and Oak in Fearrington Village hosts trunk shows that offer one-on-one time with designers and provide opportunities to shop beyond their in-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.

Line Dancing Classes at Chatham Mills
2025-10-24 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
2025-10-24 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.

Fall-O-Ween Trunk R' Treat
2025-10-24 18:00 - 21:00 | Bray Park, Bray Park T-Ball Fields, Siler City, NC, 27344, United States
Siler City Parks and Recreation treats the community to the Annual Fall-O-Ween Trunk R’ Treat on Fri, Oct 24, 6pm-9pm at the Bray Park Sports Complex. This family-friendly event will be sure to get the whole family in the Fall spirit with lots of candy, Trunk r’ Treating, inflatable attractions, music, food, games, and more.
Trunk R’ Treating activities will offer a free and safe trick or treat experience where children can stroll trunk to trunk, visiting various community organizations and businesses for free candy and learn more about their amazing community services. Concessions will be available for purchase.
Siler City Parks and Recreation is seeking businesses, organizations, agencies, churches, non-profits, and civic groups to register as trunk r’ treat vendors. Greet attendees with candy and treats, and offer any free promotional materials about your services. Registration is free and available online, in City Hall (311 N 2nd Avenue), or by emailing recreation@silercity.org. Vendors must pre-register to participate.
In the event of inclement weather, the rain date is Sat, Oct 25, 4pm-6:30pm.

Movies in the Park with Chatham County Parks and Rec
2025-10-24 18:30 - 20:30 | The Park at Briar Chapel, 1015 Andrews Store Rd., Pittsboro, NC, 27312, United States
Join Chatham County Parks, Recreation, and Cultural Resources for Movies in the Park, hosted on select Friday evenings in the fall. The movie will begin at sunset. Bring your chairs, blankets, movie snacks, and friends, and enjoy a FREE movie under the stars! The upcoming movie schedule is below:

Fri, Sep 12, 7:30pm-9:30pm The Wild Robot.
Fri, Sep 26, 7:15pm-9:15pm Mufasa.
Fri, Oct 10, 7pm-9pm Coco.
Fri, Oct 24, 6:30pm-8:30pm Inside Out 2.

This event is held outdoors at The Park at Briar Chapel by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). This event is free. All ages are welcome. See more CCPRCR events.

Witches Brew and Bonfire at Starrlight
2025-10-24 18:30 - 20:30 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
Join Starrlight Mead for a Witches Brew and Bonfire on Fri, Oct 24, 6:30pm-8:30pm. Slip into your witchy best and gather under the autumn moonlight at The Plant in Pittsboro for an evening of spooky fun and warm community vibes. Starrlight will be pouring spiced meads and ciders, including their glowing “Witch’s Brew” mead cocktail — a honey‑sweet potion with a mysterious twist.
Enjoy the crackle of the bonfire and the flicker of candles while Starrlight’s favorite tarot reader offers mystical insights. Costumes or your favorite witchy hat are highly encouraged! Indulge in s’mores, a glass of mead or cider flight, or hot mead as the night cools, and let the warmth of the fire (and your glass) keep your spirits high.
Starrlight Mead is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

QDR Homegrown Country Music Series at MOSAIC
2025-10-24 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.

Live Music with Kyler Sullivan at The MOD
2025-10-24 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Live Music with Kyler Sullivan on Fri, Oct 24, 7pm-10pm.
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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.

Vortex Paracon
2025-10-25 - 2025-10-26 | Devil’s Tramping Ground, Bear Creek, North Carolina, 27207, United States
Visit the Devil’s Tramping Ground in Bear Creek, North Carolina, the oldest haunted site in America, during Vortex Paracon on Oct 25 and Sun, Oct 26. This unforgettable experience brings together top paranormal investigation groups for merchandise, equipment, food, and entertainment. Help them raise funds for the development of the Devil’s Tramping Ground and support two paranormal investigators with their hospital bills.
Part of the Devil’s Tramping Ground Road Scenic Byway.

Trick-or-Treating and Halloween Fun at For Garden's Sake
2025-10-25 09:00 - 17:00 | For Garden’s Sake, 9197 Hwy 751 S, Durham, NC, 27713, United States
Join For Garden’s Sake for Trick-or-Treating and Halloween Fun on Sat, Oct 25, 9am-5pm. Get some extra mileage out of your Halloween costume and enjoy a festive, nature-inspired celebration. Collect candy and clues as you explore the garden center on a nature-and fall-inspired scavenger hunt. Complete the scavenger hunt to win a prize. Keep an eye out for their staff in costume. If you spot someone wearing a special badge, they have candy for trick-or-treaters. There will also be live music, pumpkin painting (supplies included with the purchase of a pumpkin), and fall drinks for sale at The Potting Shed. This event is free, family-friendly, and the perfect way to kick off Halloween.
Free parking is available on-site. See more events at For Garden’s Sake.

Celebrate Early Voting — Drag Me To The Polls!
2025-10-25 09:45 - 15:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join Chatham County Pride Alliance at The Plant for Celebrate Early Voting — Drag Me To The Polls! on Sat, Oct 25, 9:45am-3:30pm. During this non-partisan community celebration of civic engagement, you’ll enjoy a short program with drag performances, followed by a group trip to the polls (by shuttle, carpool, or drive yourself) for early voting at the Chatham County Agriculture & Conference Center.
A free shuttle will be provided 10:30am-3:30pm for easy round-trip voting. Costumes are encouraged; dressing up to vote is allowed as long as it follows electioneering and ID rules. Any Chatham County resident can vote at this site, no matter where in the county you live. After voting, stick around for The Get Down at The Plant. All are welcome! LGBTQ+ community, allies, friends & neighbors. This is a non-partisan event.
This event takes place indoors and outdoors at The Plant and the Chatham County Agriculture & Conference Center (CCACC). CCACC is ADA-compliant. 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. This event is free, and free parking is available onsite. Please leave your furry friends at home. See all events at The Plant.

Pittsboro Street Fair
2025-10-25 10:00 - 18:00 | Pittsboro, Pittsboro, NC, 27312, United States
The Pittsboro Street Fair, hosted by the Rotary Club of Pittsboro, returns to downtown Pittsboro on Sat, Oct 25, 10am-6pm. Neighbors gather and the community shines at this family-friendly event featuring over 100 vendors, live music, a Trike Race, and family entertainment.
The Pittsboro Street Fair is the Rotary Club of Pittsboro’s largest fundraiser, enabling it to continue its year-round support of our Chatham community. Admission is free, and proceeds support the Rotary initiatives, including local food drives, school supplies for local schools, Meals on Wheels, scholarships for students, and more. The club uses Postal Fish Company as its headquarters and VIP area. For more information, please contact the Rotary Club of Pittsboro at PBORotaryStreetFair@gmail.com or visit their website.
This event takes place outdoors, rain or shine, on Hanks, Fayetteville, and Salisbury Streets in downtown Pittsboro. Parking is available around downtown Pittsboro, and handicap spots are available on Hillsboro Street. No pets are allowed—please leave your furry friends at home.
Gather your friends and family for a day of fun that makes a real difference in the community!
IMPORTANT FORMS
2025 Vendor Application (Non-Food/Beverage).
2025 Food/Food Truck/Beverage Vendor Application.
2025 Sponsorship Form.
