Fall Calendar Fun in Hillsborough

Fall Calendar Fun in Hillsborough
Cover image credit: Ivan Cutler

From festivals to spooky thrills – Hillsborough’s upcoming events are a must-do for your fall calendar!



September 29th & 30th – Hosted by the Orange County Historical Museum

Get ready for Collecto-Con, a two-day extravaganza that is being produced by the Orange County Historical Museum to complement their Treasure Hunters exhibit. On September 29 and 30, collectors from around Orange County will present more items from their collections in a variety of fun and unique ways. Activities include Collecto-Couture: a vintage jewelry and fashion show with mocktails, collector presentations, an informal collector Meet-and-Greet, and Collecto-Crawl: a treasure map tour of Hillsborough’s food and beverage establishments.



Bike Fest 2023

October 7th – Hosted by the Carolina Tarwheels

The Carolina Tarwheels are excited to once again host their annual fundraising ride, Bike Fest, to give back to our local cycling community. Ride through quiet country roads and experience scenic rural vistas, historic farmsteads, and rustic churches. The pastoral heritage of the Piedmont. Multiple distances and routes to choose from.




Moorefields Bluegrass Festival

October 7th – Hosted by Moorefields Historic Site

The annual Moorefields Bluegrass Festival will not disappoint! Hosted by the historic Moorefields, this year’s lineup features the sounds of Carolina Cutups, Vintage Blue, Pickard Mountain, and so much more. 





Halloween House Visit at the Myers House

October 21 – Hosted by the Myers House

Tap into your spooky side this year with a visit to the Myers House. A “life-size replica of the infamous Michael Myers horse from John Carpenter’s 1978 horror classic HALLOWEEN”, visitors are offered the chance to tour the property and meet legendary actor and stuntman Douglas Tait.




Noir at the Bar

October 26  – Hosted by Yonder Southern Cocktails & Bar

Are you a fan of crime fiction, raffles, and a good time? Hillsborough’s Noir at the Bar has all this and more! Join Yonder Southern Cocktails & Brew for raffles, drinks, and short readings from Eryk Pruitt, Todd Robinson, Ashley Erwin, Natania Barron, Rob Creekmore, Katy Munger, and more. 




Hillsborough Halloween Spirit’s Tours 

October 27 & 28 – Hosted by The Alliance for Historic Hillsborough

Explore the darker side of Hillsborough, the Triangle’s oldest town! Join the Alliance for Historic Hillsborough and The Orange Community Players for our annual Spirits Tours. Come face-to-face with our ghostly residents to hear the chilling tales of Hillsborough’s spooky past.




Sleepy Fest

October 28  – Hosted by Sleepy Cat Records & Down Yonder Barn

Sleepy Fest is an all-ages celebration of local music, collaboration and the growing Sleepy Cat community. Held at Down Yonder Farm, a creative space in Hillsborough, NC, since 1978, Sleepy Fest features dozens of performances by artists in and around our Sleepy Cat roster, plus an art and makers market spotlighting local artisans and small businesses.





Last Fridays & Art Walk

**Recurring on the last Friday of each month – Hosted by the Hillsborough Arts Council

Keep Art Connecting Community! Last Fridays & the Art Walk are FREE town-wide celebrations of art & community hosted by the Hillsborough Arts Council. Each month visitors can experience a wide range of activities and entertainment. Be sure to check out their website for the monthly lineup and information!




Haunted Hillsborough Tours

**Recurring dates vary- Hosted by Haunted Hillsborough Tours

Join Enoch, your hauntingly good tour guide, on a walk through Hillsborough. Ghost tales, legends, and a bit of Hillsborough history will keep you on your toes. Upcoming tour dates include September 29th, 30th, and October 30th.