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

Monday, July 18, 2022 at 2:00 pm

County Commissioners Meet

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

The Chatham County Board of Commissioners typically meets on the 3rd Monday of the month, and sometimes on the 1st Monday of the month. The Work Session begins at 2:00 p.m. The Regular Session begins at 6:00 p.m. Face coverings are required for all individuals while inside the building. Individuals may locate the meeting agenda, agenda packet and livestream on the Legistar website ( using the below instructions: For first-time visitors to the site, click on the drop-down list next to the search field and select “All Years.” Then click the “Meeting Date” column to sort by most recent meeting to oldest meeting. These settings should save for any return visits to the site. For livestreaming, look for the column on the right that says "Video." Directly underneath, it when the meeting starts, the Video column will say “In Progress”. Click on the words “In Progress” and it will go to the livestream. The recording of the video will be uploaded to the same spot within 24 hours of the meeting adjourning. Once the video has adjourned and is uploaded to the site, click on specific sections of the agenda (listed underneath the video), and it will go directly to that section of the meeting. There is no need to download the video and watch the entire meeting for those interested in particular item(s). Residents wishing to sign up to speak at public input or provide comments for a public hearing may do so by completing the online form for public input and hearings. If residents do not want to speak in person, they may submit their comments in writing. The comments will be included in the meeting minutes but will not be read aloud during the meeting. Presentations are shown on screens in the chambers for residents participating in person. Questions about the meeting may be directed to Clerk to the Board Lindsay K. Ray at or 919-545-8302.

Sunday, August 07, 2022 at 12:00 pm - 4:00 pm

First Sunday Artisan Fair

Along Hillsboro Street Pittsboro, NC 27312

First Sunday has returned! As always, it's a family-friendly FUNday. Stroll the sidewalks of historic downtown Pittsboro to visit vendors selling art, jewelry, textiles, woodwork, soaps, pottery and more. Many businesses host their own sales and events. Often there's live music. The event is hosted by the Pittsboro Business Association. 

Visit the website link above for updates. Become a vendor by following the instructions at this link.

Saturday, October 29, 2022 at 10:00 am

Pittsboro Street Fair

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

Come downtown on the last Saturday of October when streets in Pittsboro are filled with local creative talent in the form of culinary, visual, and performing artists and information booths. Booth vendors should visit see the application at this link. Administered by the Pittsboro Rotary Club and hosted by the Town of Pittsboro 

Sunday, November 20, 2022 at 3:30 pm - 6:00 pm

Holiday Tree Lighting

Hillsboro Street, Downtown Pittsboro

Hillsboro Street will be closed down for the community to get in the spirit of the season in this beloved event hosted by the Pittsboro Business Association. Shop Pittsboro's unique retail businesses. Have your picture taken with Santa starting at 3:30. You won't be able to miss him in the giant snow globe in the middle of Hillsboro Street. The music portion starts at 4pm with performances by school bands, choirs, local dance troupes, and Pittsboro Youth Theatre. Ride the holiday train and play on the inflatable slide in the block between Hanks Street and West Salisbury. Hot chocolate and baked goods will be sold by student organizations. Food trucks too! This whole day is always a popular and unifying community event. Volunteers help make the magic happen.

Saturday, November 26, 2022 at 11:00 am

Shop Small Saturday

Main Street District

Local businesses are decked out for the holidays and eager to help you accomplish your holiday gift buying today. Continue your buy-local efforts by shopping at our small, independently-owned shops. Enjoy sales, specials, refreshments, Shop Small Passports for a cash raffle of $50 and 100. Visit our Welcome Center for free gift wrapping. Presented by the Pittsboro Business Association

Sunday, December 11, 2022 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, and to the west. This beloved tradition is presented by the Town of Pittsboro and is sure to get you in the holiday spirit.