Pittsboro-Siler City Convention & Visitors Bureau

Live Music: Jason Damico
2025-10-25 19:30 - 22:30 (America/New_York) | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Live Music with Jason Damico. Performances take place on the following dates:

Sat, Jun 7, 7:30pm-10:30pm.
Sat, Aug 23, 7:30pm-10:30pm.
Sat, Oct 25, 7:30pm-10:30pm.
Sat, Dec 27, 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.

Huckleberry Trail Farm Fall Festival
2025-10-26 13:00 - 18:00 | 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.

Songwriter Open Mic at bmc
2025-10-26 14:00 - 17:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
On the fourth Sunday of every month, 2pm-5pm, bmc brewing hosts a Songwriter Open Mic Night with Michael J. Brennan. Explore the unique acoustics in the halls of bmc brewing! No drums kits, no backing tracks – just songwriters sharing their best covers and originals.
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.

Spooky Yoga at Starrlight
2025-10-26 15:00 - 16:00 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
Join Starrlight Mead for Spooky Yoga on Sun, Oct 26, 3pm-4pm. Spend an hour practicing Halloween-themed outdoor yoga with Liz Lahti, then unwind with a glass of mead. The cost is $25 per person and includes one beverage. Register here.
Adults 21 and older only, please. Starrlight Mead is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music: Bad Penny at The City Tap
2025-10-26 15:00 - 17:00 | City Tap, 89 Hillsboro Street, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Bad Penny on Sun, Oct 26, 3pm-5pm.
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.

Chatham Chamber's 2025 Golf Classic
2025-10-27 08:30 - 17:00 | Governors Club Golf Course, 11000 Governors Drive, Chapel Hill, NC, 27517, United States
Join fellow leaders and changemakers for the Chatham Chamber’s 2025 Golf Classic on Mon, Oct 27, 8:30am-5pm at Governors Club Golf Course. This is your opportunity to deepen relationships, grow your brand, and invest in the work of The Chatham Chamber to fuel business success across Chatham County. They’re currently organizing: Event Sponsors, Hole Table Sponsors, and Online Auction Donations. Whether you’re swinging a club, sponsoring a hole, or donating an auction item, you’re helping shape the future of business in our region. Together you’ll champion growth, collaboration, and a future-ready Chatham County.
The schedule of events is as follows:

8:30am: Breakfast and Registration.
10am: Tee-Time.
3pm: Post-Play Reception.

Tickets are $215 for individual players and $860 for the foursome package, which includes four individual Game Day Boost add-ons (mulligan + tee buster + $20 auction credit each). Your business name will be featured as a team sponsor. Register here. Sponsorship registration is available here. This event takes place indoors and outdoors. No pets allowed.

Open Field Trip Day at Huckleberry Trail Farm
2025-10-27 09:00 - 15:00 | Huckleberry Trail Farm, 143 Pleasant Hill Church Rd, Siler City, NC, 27344, United States
Home school? Day off from school? On vacation? Come out to Huckleberry Trail Farm on Mon, Oct 27, 9am-3pm for an Open Field Trip Day. Enjoy a scavenger hunt around the farm, shoot the slingshots, explore the corn maze, discover the hidden gems still in the pumpkin patch, and picnic on one of their many picnic tables. The cost is $10 per person (no minimum group size), and the first 100 people get a free pumpkin. No hayrides on this day. No drop-offs – the farm requires an adult to accompany any kids under 18, so come out and enjoy the day, too! Pre-purchase tickets online or pay in-person at the tent (cash or charge).
More Huckleberry Trail Farm events.

Special Screening: An Act of Love
2025-10-27 17:30 - 20:30 | Chatham County Agriculture & Conference Center, 1192 US-64 W, Pittsboro, NC, 27312, United States
Join heart2heartnc as they kick off this year’s road to Death Faire with a Special Screening: An Act of Love on Mon, Oct 27, 5:30pm-8:30pm at the Chatham County Agriculture & Conference Center. Produced by Transitions LifeCare, “An Act of Love: Talking with Your Family About Serious Illness and End of Life” is a 25-minute documentary that explores the lived experiences of individuals from Black, African American, Hispanic, Latino, and rural communities as they navigate hospice and palliative care. Drawing on the personal stories of people living in the Triangle area, the film sheds light on common misconceptions and the cultural silence that often surrounds end-of-life care in these underserved communities.
Narrated by Grammy-nominated jazz artist Nnenna Freelon, the film amplifies a chorus of voices—families, caregivers, spiritual leaders, and healthcare professionals—offering a compassionate and multifaceted view of this critical time in life. These stories are especially timely in light of findings from the National Hospice and Palliative Care Organization (NHPCO), which show that Black Americans on Medicare are 13% less likely to use hospice and palliative care than their white counterparts—a disparity that underscores the urgent need for culturally sensitive outreach and education.
This free event is co-sponsored by heart2heartnc, WEBB Squared, El Vinculo Hispano/Hispanic Liaison, and The Fenwick Foundation. The evening will feature music by Diali Keba Cissokho and Will Ridenour, light finger foods by Scurlock’s Catering of Pittsboro, and will conclude with a discussion and Q&A following the screening. ​

Makers: Recycle, Upcycle, and Create!
2025-10-27 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
2025-10-27 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
2025-10-27 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.

Fearrington Farmers Market
2025-10-28 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
2025-10-28 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.

Teen Halloween Party at Chatham Community Library
2025-10-28 18:00 - 19:30 | Chatham Community Library, 197 NC Hwy 87 N, Pittsboro, NC, 27312, United States
Join Chatham Community Library for a Teen Halloween Party on Tue, Oct 28, 6pm-7:30pm. Teens in grades 6-12 are invited to enjoy candy, costume contests, and spooky fun! Costumes are strongly encouraged. This event will take place in the Holmes Family Meeting Room. No registration is required. This free, family-friendly event is open to the public.
For more information, contact youth.services@chathamlibraries.org or call 919.545.8085. See more Chatham Community Library events.

Run Club at House of Hops
2025-10-28 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
2025-10-28 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.

Music Bingo at Hops and Berry
2025-10-28 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
2025-10-28 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
2025-10-28 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
2025-10-29 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.

Pittsboro on the Patio
2025-10-29 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.

Live Music at Galloway's
2025-10-29 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.

Poetry at The Plant: Taking a Swing at Death
2025-10-29 18:00 - 19:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Come out for a special edition of Poetry at The Plant, Taking a Swing at Death on Wed, Oct 29, 6pm-7pm. Join Fair Game Beverage Company in the Wheelhouse as they feature talented local poets who will share their captivating works. This is the perfect chance to unwind, sip on your favorite beverage, and immerse yourself in the beauty of spoken word in a cozy atmosphere. Don’t miss out on this unique experience—come share in the magic of poetry!
FEATURED POETS

Tom Dow.
Scott Bryant-Comstock.
Judith Stanton.
Neil Hilborn.
Maura High.
Morrow Dowdle.
Nick Hammer.
Keith Megginson.

Local NC beers, wines, ciders, and craft cocktails will be available at the bar. 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.

Music Bingo at House of Hops
2025-10-29 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.

Mosaic Pumpkins Arts and Crafts Class
2025-10-29 18:00 - 20:30 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
Join Jessica Rigsbee for a Mosaic Pumpkins Arts and Crafts Class on Wed, Oct 29, 6pm-8:30pm at the NC Arts Incubator. You’ll start with a smooth pumpkin base, then spread on colored spackle like frosting before pressing in a mix of shiny gems, tiny charms, mosaic tiles, and other sparkly bits. Go autumn-chic, candy-colored, or totally wild—it’s your pumpkin, your rules! There will be trays of treasures for you to dig through, so your creation is 100% your vibe. No experience needed—just come ready to get a little messy, sip something cozy, and make a pumpkin that’s way too cute to leave on the porch.
Jessica provides written, visual, and verbal directions, as well as curated supplies. She will guide you through the basics and then give you space to explore and do your thing. Spanish instruction will be provided at this event. Tickets are pay-what-you-can. This event is for ages 12 and older.
See more events hosted by the NC Arts Incubator.

Jazz Nights at The Sycamore
2025-10-29 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Acoustic Irish Music Seisiún
2025-10-29 18:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for an Acoustic Irish Music Seisiún on the last Wednesday of every month, 6pm-9pm. Whether you’re just beginning your music journey, a seasoned pro, or just love to listen, bring your instruments and passion for Irish music for an evening of lively tunes and great company. Musicians will be upstairs.
See more events at Doherty’s.

Wellness Wednesdays - Indoor Classes at Barre3
2025-10-29 18:30 - 19:30 | Barre3 Chatham Park, Mosaic Boulevard, Pittsboro, North Carolina, 27312, United States
Join MOSAIC at Chatham Park for Wellness Wednesdays – Indoor Classes, hosted select Wednesdays, Jul-Oct, 6:30pm-7:30pm.
This event, hosted by Barre3 Chatham Park, is FREE and open to the public, but registration is required. See the full schedule below and find your link to register:

Wed, Jul 2, 6:30pm-7:30pm Register.
Wed, Jul 9, 6:30pm-7:30pm Register.
Wed, Jul 16, 6:30pm-7:30pm Register.
Wed, Jul 23, 6:30pm-7:30pm Register.
Wed, Jul 30, 6:30pm-7:30pm Register.
Wed, Aug 6, 6:30pm-7:30pm Register.
Wed, Aug 13, 6:30pm-7:30pm Register.
Wed, Aug 20, 6:30pm-7:30pm Register.
Wed, Aug 27, 6:30pm-7:30pm Register.
Wed, Oct 1, 6:30pm-7:30pm Register.
Wed, Oct 8, 6:30pm-7:30pm Register.
Wed, Oct 15, 6:30pm-7:30pm Register.
Wed, Oct 22, 6:30pm-7:30pm Register.
Wed, Oct 29, 6:30pm-7:30pm Register.

Bring a water bottle. A water fountain is located behind the stage. Fitness equipment will be provided. Food and beverages are available for purchase at MOSAIC. This event is held indoors at Barre3 Chatham Park. See more events hosted by MOSAIC at Chatham Park.

Flower Arranging Workshop with Koshu and Fleurish
2025-10-29 18:30 - 20:00 | Fleurish Bloom Bar and Boutique, 192A Lorax Lane, Pittsboro, 27312, United States
Celebrate Autumn and Japan’s Chrysantemum Festival (Kiku Matsuri) with this Flower Arranging Workshop with Koshu and Fleurish on Wed, Oct 29, 6:30pm-8pm, led by Carey Taylor of Fleurish Bloom Bar & Boutique. Make a centerpiece featuring fresh chrysanthemums and sip on a floral sake tasting by Koshu Sake Bar featuring two chrysanthemum-inspired sake and two sake brewed with flower blossom yeast (hana kobo). Registration is $75 per person and includes all materials and the sake tasting. RSVP by Sun, Oct 26.
Adults 21+ only, please. Fleurish and Koshu are part of The Plant in Pittsboro. Koshu is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at The Plant.

Our State Book Club: History, Mystery, and Dracula
2025-10-29 19:00 - 20:30 | Fearrington Barn, 500 Market Street, Pittsboro, NC, 27312, United States
Join McIntyre’s Books for an Our State Book Club: History, Mystery, and Dracula – An Evening with Elizabeth Kostova on Wed, Oct 29, 7pm-8:30pm in the Fearrington Barn. Get ready for a spellbinding evening of conversation with internationally best-selling author Elizabeth Kostova, whose gothic thriller The Historian is Our State’s October Book Club selection. The New York Times best-selling author Wiley Cash will lead a lively discussion and take part in an audience Q&A. Discover the eerie inspirations behind The Historian, explore its chilling ties to folklore and history, and meet Elizabeth for a book signing following the event.
Wine, coffee, and light hors d’oeuvres will be served. Tickets are $50 per person.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.
