Wilfred grew up with a great sense of pride in his "great-great-great-great-grandpappy," Fambing Woo, and with his Confederacy heritage. He was very active in Civil War reenactments, and was named the alternate sword-master at the Southern Area Regional Volunteer Infantry Reenactment regiment on three occasions. His grandfather, Wilfred Woodruff IV, was to be buried wearing his reenactment uniform and holding a sword that belonged to Fambing.