Bookmark this page for events, meetings, and opportunities happening around Pittsboro’s Main Street District.

Sunday, September 22, 2019 at 3:00 pm - 6:00 pm

12th Annual Pepper Festival

Downtown Pittsboro

We're thrilled to be working with Abundance NC to bring the 12th Annual Pepper Festival to downtown Pittsboro. The Pepper Festival is a celebration of sustainable agriculture, local farmers, and the creativity of the Piedmont's top chefs, brewers and artisans. Pepper Festival attracts around 3,000 folks who enjoy live music, learning and discovery – including a kid’s craft and fun zone – and eating delicious pepper-themed dishes made with locally grown sweet, hot and smoky NC peppers. Volunteers are needed. Tickets are available at the Pittsboro Pepper Festival Page on Eventbrite.

Saturday, October 26, 2019 at 10:00 am - 4:00 pm

Pittsboro Street Fair

West of Hillsboro Street and North of Business 64, Downtown Pittsboro

Join us on the last Saturday of October when the streets of Pittsboro are filled with local creative talent in the form of culinary, visual, and performing artists and informational booths. Look for The Main Street Pittsboro booth to learn more about the work we're doing in concert with the Pittsboro Merchants Association and the Chatham Historical Association to keep downtown a vital destination. Hosted by the Town of Pittsboro

Sunday, November 24, 2019 at 3:30 pm - 6:00 pm

5th Annual Tree Lighting

Hillsboro Street, Downtown Pittsboro

This kick off to Pittsboro's Holly Days presented by the Pitttsboro Business Association features special events at downtown businesses, a giant snow globe, school choirs, and carolers and culminates with the lighting of an 18-foot tree at the historic Chatham County Courthouse. Visits with Santa Claus start at 3:30pm, festivities on Hillsboro Street start at 4pm and go until after dark.

Saturday, November 30, 2019 at 10:00 am - 5:00 pm

Shop Small Saturday

Main Street District

We believe in all things local and today is the day to set that intention and follow through with support of all of our small, locally-owned and -operated downtown businesses. Find our table on Hillsboro Street to get free gift wrapping, Shop Small reuseable canvass bags, and our Pittsboro Boomerang Bags.

Sunday, December 08, 2019 at 3:00 pm - 4:00 pm

Pittsboro Holiday Parade

Business Highway 64 east to west

Marching bands, handcrafted floats, dance teams, horse-drawn wagons, and Santa Claus (of course) comprise a moving holiday celebration from the east side of town through the center of downtown in this beloved tradition presented by the Town of Pittsboro sure to get you in the holiday spirit.

Saturday, December 14, 2019 at 2:00 pm - 6:30 pm

Miracle on Hillsboro Street

Chatham County Courthouse, 9 East Street, Pittsboro, NC 27312

We invite everyone to get into the act when Santa Claus goes on trial in the Historic Chatham County Courthouse with local actors and legal experts. The Pittsboro Business Association's 2019 Holly Days closes with Miracle on Hillsboro Street. *Times are noted for reference only and still need to be confirmed. Check back for particulars on this beloved seasonal event.