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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

Game Dinner at The Sycamore

The Sycamore at Chatham Mills 480 Hillsboro Street, Pittsboro

Delight in the wild side of dining at The Sycamore! Our Game Night menu is a true masterpiece, featuring a delectable array of dishes paired with optional wines that are nothing short of exquisite. Join us for a memorable evening of flavors with the most unique cuts and ingredients. Reserve your spot today by e-mailing [email protected].