Events 2018-06-09T04:15:31+00:00

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

Sunday, April 07, 2019 at 12pm - 4pm

First Sunday Artisan Fair

Along Hillsboro Street Pittsboro, NC 27312

Stroll Pittsboro's brick sidewalks, shop our stores, visit the Chatham Historical Museum, enjoy live music, food trucks, and the booths of artisans and local organizations from March to December. Want to be a vendor? Get more information and sign up for a booth space from the Pittsboro Business Association

Sunday, May 19, 2019 at 5pm - 8pm

Food, Farm & Art Dinner

Downtown Pittsboro, NC 27312

Pittsboro's creative culture is a way of life. Culinary artistry, visual and performing artistry, and our appreciation for small family farms draw visitors who become neighbors. In recognition of these fundamental aspects of the good life we enjoy here, Main Street Pittsboro will present our "Food, Farm, & Art Dinner: Celebrating Main Street Pittsboro's Unique History". Join friends and neighbors at a table in the center of Hillsboro Street to discover, acknowledge, and honor the skills of local chefs, farmers, and artists in this fundraiser to help us continue our mission of revitalizing our historic downtown district. Mark your calendars and stay tuned for more information.

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

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 3pm - 6pm

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 10am - 5pm

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 3pm - 4pm

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.