Fall Fun in Pittsboro: Your Ultimate Guide to Local Festivals and Family-Friendly Events

Autumn in Pittsboro is more than just colorful leaves and crisp air, it’s a season packed with community celebrations, creative experiences and family-friendly fun. Whether you’re looking to explore a corn maze, enjoy live music or celebrate cultural traditions, this guide covers all the exciting events happening in and around Pittsboro this October.

Huckleberry Fall Festival – Weekends Through October 26

Just off Hwy 64 between Pittsboro and Siler City, the Huckleberry Fall Festival is a charming countryside escape. Open Saturdays (10 a.m. – 6 p.m.) and Sundays (1 – 6 p.m.), the festival offers:

• A sprawling corn maze
• Tractor-drawn hayrides to the pumpkin patch
• A cotton patch and mini Field of Dreams
• Refreshments, fall décor and merchandise for sale

Each weekend features themed activities:

• Oct. 4–5: Huck’s Feed the Hungry – Bring a canned food item for $1 off admission; donations go to CORA, sponsored by Piggly Wiggly.
• Oct. 11–12: Who’s Your Huckleberry – Free admission for teachers, first responders, healthcare workers and military personnel with ID.
• Oct. 18–19: Scout Weekend – Scouts in uniform get a special $9 admission, sponsored by The Sycamore.
• Oct. 25–26: School Field Day – Wear school gear for $1 off admission.
• Oct. 25: Flashlight Maze – Explore the corn maze after dark from 6 – 9 p.m. Bring your flashlight!

Oktoberfest at The Plant – Sunday, October 5 | 12 – 6 p.m.

Celebrate Bavarian culture at Oktoberfest at The Plant, located at 192 Lorax Lane in Pittsboro. This free event includes:

• Live music throughout the day
• Bavarian pretzels and local bratwurst
• A kids’ costume contest
• A stein holding contest (prelims 12 – 4 p.m. at bmc brewing; finals at 5 p.m. on the main stage)

It’s a festive afternoon for all ages, blending local flavor with traditional Oktoberfest fun.

Track ‘n’ Treat Halloween Train Ride – October 11, 18, 25

All aboard the Track ‘n’ Treat Halloween Express at New Hope Valley Railway in New Hill! This spooky-but-friendly train ride features:

• Halloween scenes with witches, pumpkins and Dracula
• Costumes encouraged
• Departures at 2:15, 3:30, 4:45, 6:30 and 7:45 p.m.

Tickets are $18.61 and sell out fast. A sensory-friendly ride is available on October 15 at 10:30 a.m. and 12 p.m. — no live actors or loud noises. For adults, the Boo ‘n’ Brew Train Ride on October 24 includes food and beer, with the same Halloween décor and actors.

Chapel Hill Festifall Arts Markets – October 18 & November 1 | 12 – 5 p.m. 

Chapel Hill’s Festifall Arts Markets return with two vibrant street festivals at 140 West Franklin Street:

• Oct. 18: Local art vendors, musicians and performers from across the Triangle.
• Nov. 1: A special Día de los Muertos celebration with themed art, music and cultural experiences.

Both events are free and open to all, offering a chance to engage with the arts and celebrate community creativity.

Hallow-Eno – Saturday, October 18 | 3:30 – 6:30 p.m.

Durham’s Hallow-Eno at West Point on the Eno is a free, family-focused event for kids 12 and under. Enjoy:

• Campfire stories and treats
• Crafts and games
• Food trucks and more

No registration required — just show up and enjoy the fun in a beautiful riverside park setting.

Pittsboro Street Fair – Saturday, October 25 | 10 a.m. – 6 p.m. 

The heart of downtown Pittsboro comes alive during the Pittsboro Street Fair, a beloved annual tradition that draws thousands of visitors. Held rain or shine on Hanks, Fayetteville and Salisbury Streets, the fair features:

• Local food trucks and vendors
• Live music and performances
• Artisan booths and handmade crafts
• Nonprofit showcases
• Activities for kids and families

Admission is free, and a complimentary shuttle from CCCC makes parking easy. Organized by the Rotary Club of Pittsboro, the event supports scholarships, food programs and other community initiatives through Rotary’s mission of “Service Above Self.”

Trunk or Treat Fall Festival – Saturday, October 25 | 2 – 5 p.m.

Hosted by Chatham County Parks & Recreation, the Trunk or Treat Fall Festival at Southwest District Park (Bear Creek) is a Halloween favorite. From 2 – 4 p.m., enjoy:

• Pumpkin carving and painting
• Hay hunt and seasonal games
• Bounce houses and crafts
• Costume contest and photo station

From 4 – 5 p.m., the Trunk or Treat begins, with decorated vehicles handing out candy. Admission is free, and local groups are invited to participate by registering a trunk display.

Scare-o-lina Skies at Morehead Planetarium – October 25 & 31

Explore the spooky side of astronomy at Scare-o-lina Skies in Chapel Hill:

• Oct. 31: Adult/teen show at 4:30 and 6 p.m. featuring myths and monsters of the night sky.
• Oct. 25: Star Families: Scare-o-lina Skies – A kid-friendly version from 12 – 1 p.m. for ages 7–12.

Tickets range from $13.95 to $15.95, with discounts for seniors, students and military.