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Pittsboro Holly Days 2023

Downtown Pittsboro 9 Hillsboro St, Pittsboro

Visit downtown Pittsboro for a month of family-friendly holiday celebrations! Special events happening November 19 - December 18. Check our full event calendar for even more.   Tree Lighting Celebration Sunday, November 19, 3:30-6:30 p.m. An old-fashioned Christmas celebration featuring school choirs, carolers, Santa Claus, shopping, and more. Festivities culminate with the lighting of a 18-foot Christmas tree at the historic Chatham County Courthouse. Businesses are hosting special events all day. Santa visitation starts at 3:30! Don't forget to bring your camera/camera phones. Small Business Saturday Saturday, November 25, all day Shop small, shop local! You can find great gifts for everyone on your list from local businesses in Pittsboro and Chatham County. Come downtown and check us out! We’ll have gift wrapping and shoppers’ passports (visit local stores and be entered for drawings for gift cards) at the Welcome Center. First Sunday Artisan Fair Sunday, December 3, 12-4 p.m. An artisan market featuring crafts, music, and food. Shops, restaurants and the Historical Museum host special events. Pittsboro Christmas Parade Sunday, December 10, 3 p.m. Marching bands, dancers, holiday revelers, and Santa Claus parade through downtown in this annual tradition. Brought to you by the Town of Pittsboro. Pittsbro! Thursday, December 14, 4-8 pm Last-minute shopping for the shopping-challenged!   Thanks to our sponsors! Pictures from the 2023 Lighting! Save

Live Jazz on Wednesdays at The Sycamore–GLK Trio

The Sycamore at Chatham Mills 480 Hillsboro Street, Pittsboro

Jazz nights are continuing on Wednesdays so don't miss out on the chance to hear some great holiday jazz this month, sprinkled in alongside your classic favorites. Here are our upcoming performers 11/29- GLK Trio 12/6- Dave Quick 12/13- Lauren Meehan 12/20- Steve Hobbs Trio 12/27- Tony Galiani Band