Cary Hosts Ole Time Winter Festival Living in Cary NCCary hosts the Ole Time Winter Festival this Saturday from 12-4. In the bustling downtown Cary district, there will be live music, caroling, shopping from local vendors, and lots of great discounts from downtown Cary businesses. Of course, there will also be food trucks and craft beers.Santa will be at the Matthews House for pictures and cookies – free and open to everyone! Bring an unwrapped toy for donation to the Carying Place. This event is put on by the Heart of Cary Association.