Huckleberry Trail Farm Fall Festival
2025-10-12 13:00 - 18:00 (America/New_York) | Huckleberry Trail Farm, 143 Pleasant Hill Church Rd, Siler City, NC, 27344, United States
Visit the Huckleberry Trail Farm Fall Festival for a corn maze, a pumpkin patch (select a pumpkin from the vine), a cotton patch, and a fall atmosphere. Find designated quiet areas set up the entire season. The family’s mission is to bring all kids back to the outdoors with the goal of making many of the farm activities wheelchair-accessible and autism-friendly.
Huckleberry Trail Farm celebrated 10 years in 2021. Explore the corn maze, pumpkins, and fall decorations, and purchase refreshments. Take a ride on a tractor-drawn hayride (for transportation down to the pumpkin patch). Merchandise is available on-site for purchase, too. Guests to the farm will find a pumpkin patch (cut your own pumpkin right off the vine), a cotton patch, and a mini Field of Dreams.
Hours, Directions, & Pricing
Saturdays, 10am-6pm and Sundays, 1pm-6pm.
The last ticket is sold one hour before closing. The last hayride is 30 minutes before closing. Find admission and ticket information here.
Huckleberry Trail Farm is conveniently located on Hwy 64 right between Pittsboro and Siler City, just 30 minutes from Cary, Apex, Chapel Hill, Durham, and Greensboro. It’s an easy drive over a shining lake and rushing river, through the beautiful rolling country, and past farmland complete with horses, cows, and red barns.

Live Music: Dr. Scott
2025-10-12 14:00 - 15:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Dr. Scott on Sun, Oct 12, 2pm-3:3pm.
Dr. Scott is a fingerstyle guitarist and vocalist with 15 years of experience playing a genre-spanning mix of music, including blues, jazz, folk, Spanish, classical guitar, bluegrass, country, and classic rock. Known for his technical guitar playing and rich baritone vocals, his performances feature smooth melodies, thumb-thumping rhythms, and familiar favorites sure to get your feet tapping and your knees slapping. Featuring covers of artists like John Prine, Dave Van Ronk, Ray Charles, Doc Watson, Leon Redbone, the Beatles, and the occasional original.
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.

Build a Bouquet at FireClay
2025-10-12 14:00 - 16:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for a pop-up Build a Bouquet workshop from Poe Family Farm on Sun, Oct 12, 2pm-4pm. Learn all the tips and tricks needed to create a beautiful, locally grown bouquet to take home – all while enjoying a delicious glass of wine! The cost is $25 per person. Register here.
FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Drawing 2 Workshop (Intermediate)
2025-10-12 14:00 - 17:00 | The Arts Center, 964 East Street, Suite 105, Pittsboro, NC, 27312, United States
Rapidly improve your drawing skills with quick, mind-expanding drawing exercises. The Drawing 2 Workshop (Intermediate) continues where Drawing 1 left off: covering the remaining “seeing skills” necessary to draw confidently. You’ll start with loose and messy work, progressing to more finished pieces. You’ll receive demos, individual guidance, and lots of practice. Instructed by Stacye Leanza. This two-class session takes place Sat, Oct 11, and Sun, Oct 12, 2pm-5pm. Registration opens Mon, Aug 25, and closes Mon, Oct 6. Drawing 1 is a prerequisite.
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 $70 per person. Ages 15+ are welcome. See more CCPRCR events.

Live Music: Mouthsounds
2025-10-12 16:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Mouthsounds on Sun, Oct 12, 4pm-5pm. Mouthsounds blends quirky alternative power-pop with flashes of swirling moody rock, dancehall groove, and 80’s grit. The lineup — Jane Allen Wilson (vocals), Matthew Levy (guitar, backing vocals), Mary Anne Barckhoff (bass), and Nathan Logan (drums, backing vocals) keeps it turning with infectious numbers that will have you singing out loud in the shower.
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.

Twilight Tours at Carolina Tiger Rescue
2025-10-12 17:30 - 19:00 | Carolina Tiger Rescue, 1940 Hanks Chapel Road, Pittsboro, NC, 27312, United States
Carolina Tiger Rescue’s popular Twilight Tours run from April through October on Friday, Saturday, and Sunday evenings. Tours are for adults only (guests ages 18 years and older). Twilight tours are a more intimate experience to meet CTR’s animals. During these tours, guests are the only visitors in the sanctuary. The work of the day is done, and the guests have the sanctuary all to themselves. Enjoy a quiet evening with the cats, and you might just be lucky enough to be serenaded by the lions! After all, they are still wild animals! As with all their tours, we cannot guarantee what the cats will do, but it’s hard to have a bad evening with animals.
Your Twilight Tour will last for about 1 ½ hours. Please arrive 15 minutes early. Trained volunteer tour guides will walk you through the animal sanctuary. You will learn about the various species living at Carolina Tiger Rescue and the challenges they face in the wild, as well as the difficulties they encounter in captivity. You will have the opportunity to ask questions and take photos, but please note that there will be no physical contact with the animals.
The upcoming schedule for Twilight Tours is below (weekends only):

August: Fri-Sun, 6pm-7:30pm.
Fri, Sep 5-Fri, Sep 19, 5:30pm-7pm.
Sat, Sep 20-Sun, Oct 12, 5pm-6:30pm.

Advance tickets are required for attendees (no walk-ins available). Tours are offered from April to October on Friday, Saturday, and Sunday evenings, rain or shine. The cost is $32 per person, and a maximum of 25 people are allowed to attend each tour. Tickets are available 8 weeks before your visit.
See more events at Carolina Tiger Rescue.
BEFORE YOU VISIT
There are several things CTR would like you to know before booking your tour. Please reach the information below before purchasing your tickets:

All tours go out rain or shine. In the event of an extreme weather event, Carolina Tiger Rescue will contact guests to inform them if a cancellation is necessary.
Photos may be taken during your tour after you’ve signed your visitor release.
The Education Center is wheelchair accessible; however, the gravel and grass paths may be more challenging to navigate for those with impaired mobility. Golf carts are available to assist guests who need them. If you have accessibility concerns, please call 919.542.4648 to make arrangements before your visit.
GPS may not provide accurate directions to CTR’s location. They recommend using the directions from their website to ensure a successful arrival.
CTR does not allow outside animals anywhere on the property. Please leave your pets at home.

Tap Dancing - Advanced
2025-10-13 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.

Makers: Recycle, Upcycle, and Create!
2025-10-13 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.

Euchre Mondays at bmc
2025-10-13 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.

Opinionation Trivia at Hops and Berry
2025-10-13 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come to Hops and Berry-Pittsboro for Opinionation Trivia every Monday, 7pm-9pm. 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.

Better Business Decisions – A Business Acumen Simulation
2025-10-14 09:00 - 17:00 | 79° West, 120 Mosaic Blvd, Suite 120, Pittsboro, NC, 27312, United States
Join 79° West for Better Business Decisions – A Business Acumen Simulation on Tue, Oct 14, 9am-5pm. This is a hands-on, competitive simulation where participants run a company, making strategic and financial decisions that impact performance. This interactive program builds financial confidence and strategic thinking—without requiring a background in finance. Compete with your peers to build the most successful company, making big decisions that drive real results. Along the way, you’ll gain profound financial know-how—and maybe even some bragging rights. Key takeaways include:

How financial decisions impact business outcomes.
Fundamentals of cash flow and profitability.
The balance between short-term wins and long-term success.

This is a typical workshop – get ready for fast-paced, team-driven exercises that provide information built to last. Whether you’re new to business or have years of experience, this FREE workshop builds a solid foundation in financial awareness.
This indoor event is free for coworking members and the public. 79° West is part of MOSAIC at Chatham Park. See all events at MOSAIC.

Quiltmaker Pay-What-You-Can Lunch at Cafe Root Cellar
2025-10-14 11:30 - 14:00 | Cafe Root Cellar, 35 Suttles Road, Pittsboro, NC, 27312, United States
Join Quiltmaker Cafe at Cafe Root Cellar for a Pay-What-You-Can Lunch on Tue, Oct 14, 11:30am-2pm. Chef Sera Cuni is opening her doors—and her heart—to support a beautiful community mission. Enjoy a delicious lunch at Cafe Root Cellar and pay what you can. All proceeds will benefit The Quiltmaker Cafe, a pay-what-you-can restaurant set to open soon in downtown Pittsboro. Dine-in and take-out options will be available from a special menu. Call ahead at 919.542.1062 to order.

Fearrington Farmers Market
2025-10-14 15:00 - 17:00 | Fearrington Village, 2000 Fearrington Village Center, Pittsboro, NC, 27312, United States
The Fearrington Farmers Market is a producers-only market open Mar-Oct, Tuesdays, 4pm-6pm, and Nov-Feb, Tuesdays, 3pm-5pm, year-round in Fearrington Village. Bring reusable tote bags and plan to explore the many local vendors. You also might chat with the farmers, see old friends, or meet new ones! It’s a welcoming, inclusive, and friendly atmosphere that encourages healthy, happy living.
Fearrington Farmers Market has more than 3 dozen members and is now in its 30th season. Not all vendors are there every week, but some vendors are there every week, year-round. Each market features live music. Vendors include Celebrity Dairy, In Good Heart Farm, and bmc brewing. See their full list of vendors.
Come early if you’d like to review what is being offered; sales begin at the scheduled time, signaled by the bell. Bring along small bills ($20 or lower) to pay for your purchase. Some vendors accept credit and debit cards, and most will accept checks. This event takes place outdoors, rain or shine. Entry is free. Leashed, well-behaved pets are welcome. See more events at Fearrington Village.

Yoga at Bynum Front Porch
2025-10-14 18:00 - 19:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Unwind and recharge with Yoga at Bynum Front Porch, hosted every Tuesday, 6pm-7pm. This all-levels class offers a welcoming space to stretch, breathe, and connect with the community – bring your mat and a positive spirit. This event is free to attend, with a suggested donation of $15. Directions.
Year-round events, including a Christmas tree sale and a holiday bazaar. See a feature about geocaching in Bynum, produced by UNC-TV for NC Weekend and sponsored in part by the NC Division of Tourism, Film, and Sports Development.

Run Club at House of Hops
2025-10-14 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.

Live Piano Music at The Sycamore
2025-10-14 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.

CCBA Monthly Meetings
2025-10-14 19:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
The Chatham County Beekeepers’ Association (CCBA) hosts meetings on the second Tuesday of every month from 7pm-9pm at Starrlight Mead. The meeting begins with CCBA business, followed by a guest speaker, and finally, an open Q&A. Meetings with local presenters will be in person only. Meetings with remote speakers are available virtually. Everyone is welcome to attend meetings – you do not have to be a member. For more information about meetings, contact info@chatham-beekeepers.org.
This event is free and takes place indoors. 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 The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at Hops and Berry
2025-10-14 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. 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.

Pub Trivia at Doherty's
2025-10-14 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
2025-10-14 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.

Coffee Klatch at Bynum Front Porch
2025-10-15 07:00 - 10:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Start your day with good coffee or tea and great conversation at Weekly Coffee Klatch with Bynum Front Porch Music, hosted every Wednesday, 7am-10am. Drop in for a warm cup, friendly faces, and casual community chats – everyone is welcome! Directions.
Year-round events, including a Christmas tree sale and a holiday bazaar. See a feature about geocaching in Bynum, produced by UNC-TV for NC Weekend and sponsored in part by the NC Division of Tourism, Film, and Sports Development.

Wake Up Wednesday at Carolina Brewery
2025-10-15 08:00 - 09:30 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Wake Up Wednesdays are hosted at Carolina Brewery & Grill every third Wednesday, 8am-9:30am. This networking includes breakfast, coffee, and new guest speakers each month. The fee to participate is $7 cash or $8 by card. If you do bring cash, do your best to bring exact change. If you pay by check, make it out to the Carolina Brewery. Please consider bringing a tip for your server.
See more events at Carolina Brewery & Grill.

Pittsboro on the Patio
2025-10-15 08:30 - 10:00 | West End Kitchen and Catering, Pittsboro, North Carolina, 27312, United States
Join West End for Pittsboro on the Patio hosted every Wednesday, 8:30am-10am. During this community mixer event, enjoy complimentary fresh coffee from Pittsboro’s own Aromatic Roasters on the West End patio while meeting and creating great conversations with community members and leaders.
See more events at West End Kitchen and Catering.

Tap Dancing - Intermediate
2025-10-15 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.

Sound Unity - Music Group
2025-10-15 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.

Beginner Archery Clinic
2025-10-15 17:00 - 18:00 | Northwest District Park, 2413 Woody Store Road, Siler City, NC, 27344
In this Beginner Archery Clinic, participants will learn the basics of archery safety, equipment, and form from a USA Archery-certified coach. Personal bows may be used with the instructor’s permission. No experience is needed. All supplies are provided. This class occurs every Wednesday, Sep 10-Oct 22, 5pm-6pm. Registration opens Mon, Aug 4, and closes Tue, Sep 9.
This event is held indoors at the Northwest District Park by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). Registration is $50 per person. Ages 10+ are welcome. See more CCPRCR events.

Live Music at Galloway's
2025-10-15 17:00 - 19:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesday-Saturday, 5pm-7pm. Check out their events calendar to see who’s playing.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Wine Education 101 - The Pacific Northwest
2025-10-15 18:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro St, Suite D, Pittsboro, NC, 27312, United States
Join Vino’s!! next Wine Education 101 Seminar: The Pacific Northwest on Wed, Oct 15, 6pm-7pm. The Pacific Northwest wine region comprises Oregon and Washington. These states are excellent wine-producing regions. What sets them apart from many other New World wine-producing areas is their ability to straddle the stylistic divide between Old and New World. Both states benefit from warm, stable West Coast weather. It is the warm weather that yields the lively, ripe fruit of New World wines. However, their northern longitude gives them the benefit of cool nights, allowing the grapes to retain that refreshing acidity that Old World wines are known for. The predominant grape varietals in these regions are Chardonnay, Pinot Gris, Merlot, and Cabernet Sauvignon. Over the years, Oregon has become known as the home to outstanding Pinot Noirs, ones that rival the top Pinot Noirs from across the world. Washington’s history doesn’t go back as far as that of California, but it has recently had a tremendous increase in its quality curve and is the second-largest wine-producing state in the United States!
This wine seminar will discuss the different AVAs within Oregon and Washington and cover all the predominant grape varietals grown in these areas. There are 42 spaces available for this event. The cost is $40 per person, which includes admission to the class plus one pre-selected bottle of wine to take home. Discounts will be applied to any other wines purchased. Admission must be paid in advance. If you are interested, please make reservations by either emailing anna@vinowineshopnc.com or calling 919.542.3922 no later than Fri, Oct 10.
WINES

2024 Lemelson White Pinot Noir, Willamette Valley, Oregon.
2023 Barnard Griffin Riesling, Columbia Valley, Washington.
2021 J. Christopher Basalte Pinot Noir, Willamette Valley, Oregon.
2022 Novelty Hill Syrah, Columbia Valley, Washington.
2021 Januik Cabernet Sauvignon, Red Mountain, Washington.

All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Music Bingo at House of Hops
2025-10-15 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
2025-10-15 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.
