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Pittsboro Holly Days 2022

Downtown Pittsboro 9 Hillsboro St, Pittsboro

Visit downtown Pittsboro for a month of family-friendly holiday celebrations! Special events happening November 20 - December 18. Check our full event calendar for even more. Tree Lighting Celebration Sunday, November 20, 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 26, 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 4, 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 11, 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. Pittsboro by Luminaria Thursday, December 15, 3 p.m. - 7 p.m. Come downtown, shop, sip, dine, and enjoy the downtown area lit by luminaria.   Thanks to our sponsors! Save

Live Jazz on Wednesdays at The Sycamore

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 performers for December: 12/7- Kris Whitenack trio 12/14- Lauren Meehan Band 12/21- Dave Quick 12/28- Tony Galiano So make a reservation and join us for dinner tonight! Lounge menu served in the dining room, and the lounge, and our full dinner menu as well.