Kenneth Whynot Sr., 86, of Windham, passed away on October 5, 2022 at Gosnell Memorial Hospice House in Scarborough. He was born on the Fourth of July in 1936, one of five children to the late George and Florence (Page) Whynot. Kenneth started his career in the trucking industry early on at the age of 15, where he would work alongside his father. He was a truck driver all his life, beginning with Emery Waterhouse Co. and retiring from Yellow Freight as a Teamster. While working at Emery Waterhouse, he was introduced to his wife, Claudia (Kutcher) by her mother, who also worked there at the time. They fell in love and were happily married for 66 years. Kenneth and Claudia raised their three children on Montgomery Rd. in Windham, where they lived for years. During their retirement, they loved riding their motorcycle, taking their RV down to South Carolina to visit with family, making many friends on their camping adventures, singing karaoke at the American Legion, & going on many outings with the Circle of Friends. Kenneth is survived by his daughters: Tambrey Francis & her partner Rodrick Sawyer; Stacy Gendrolis & her husband Michael; and daughter in law Kathy Whynot, as well as five grandchildren: Betsey Sanborn & husband Teddy; Danielle Dulac & husband Brandon; Scott Gendrolis & partner Kerri Moreau; Karrie Sargent & husband Steve; and Kristopher Whynot & wife Laura. He will also be missed by 10 great-grandchildren and three great-great-grandchildren. He was predeceased by his son, Kenneth "Spike" Whynot Jr., as well as his three brothers and sister. The family would like to thank Gosnell Memorial Hospice for their excellent care and compassion. In lieu of flowers, donations may be made to Gosnell at 11 Hunnewell Rd., Scarborough, ME, 04074. A Celebration of Life will be held on October 15, 2022, from 1-3PM at Windham Hill UCC, 140 Windham Ctr. Rd, Windham ME.