Sunday, July 03, 2022 at 5:00 pm - 9:00 pm

Summer Fest!

Downtown Pittsboro, NC 27312

Summer Fest in Pittsboro always falls around Independence Day and includes food trucks, craft booths, live music, dancing, games, contests and inflatable activities and is hosted by the Pittsboro Business Association. Mark your calendars and join us downtown in the parking lot between Salisbury, Fayetteville, and Hanks Streets.

Saturday, October 29, 2022 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 a downtown block in Pittsboro is 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 collaboration with the Pittsboro Merchants Association and the Chatham Historical Association to keep downtown a vital destination. 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.