Saturday, October 30, 2021 at 10:00 am

Pittsboro Street Fair

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

Date is based on the timing of the event in previous years. Please check back to confirm. 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 21, 2021 at 2:00 pm - 6:00 pm

Annual Tree Lighting

Hillsboro Street, Downtown Pittsboro

Date is based on the timing of the event in previous years. Please check back to confirm. The day of the tree lighting kicks off Pittsboro's Holly Days -- a series of seasonal events happening each weekend in December in downtown Pittsboro. We're proud to be an on-going major sponsor of Holly Days as presented by the Pittsboro Business Association ("PBA"). On the day of the tree-lighting visitors might expect live performances by choirs, bands, dancers, excerpts of theatre performances, and refreshments in downtown shops with seasonal sales plus visits with Santa Claus -- all prior to the tree lighting. This whole day has been a very popular and unifying community event. Find it in Pittsboro! More info soon at the PBA website.

Saturday, November 27, 2021 at 10:00 am

Shop Small Saturday

Main Street District

Date is based on the timing of the event in previous years. Please check back to confirm. 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 cash raffles. Visit our Welcome Center for free gift wrapping. Presented by the Pittsboro Business Association

Sunday, December 12, 2021 at 3:00 pm - 4:00 pm

Pittsboro Holiday Parade

Business Highway 64 east to west

Date is based on the timing of the event in previous years. Please check back to confirm. 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.

Sunday, December 19, 2021 at 2:00 pm - 3:00 pm

Miracle on Hillsboro Street

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

Date is based on the timing of the event in previous years. Please check back to confirm. Miracle on Hillsboro Street is historically the final event during Pittsboro's Holly Days -- a series of seasonal events that happen downtown. Everyone can get into the act when Kris Kringle goes on trial in the Historic Chatham County Courthouse with local actors and legal experts. Bring the kids with a letter to Santa Clause telling him what they love about him. Their letter might even be picked to be read at the show! Don't miss this local tradition! Main Street Pittsboro is proud to be an on-going major sponsor of Holly Days as presented by the Pittsboro Business Association ("PBA").