Chester W. Dudley III, 61, of Keeling, VA passed away peacefully in his sleep on April 28, 2019. Chet was born in Holyoke, MA on October 21, 1957 to Chester W. Dudley and the late Pauline (Diliberto) Dudley. He was a 1975 graduate of Holyoke High School, a Veteran of the U.S. Army’s Infantry Division (MP), and was retired from the Connecticut Department of Corrections. He was predeceased by his mother, Pauline, and is survived by his father, Chester W. Dudley; his children, Christina Dudley, Cassandra (John) Scearce, Shannon (Jason) Dudley Alsbaugh, and Kelly (Del) Benz Chattin, and their mother, Diana Lee Dudley. He leaves behind his 9 beloved grandchildren, Tatyana, Rebecca, Nikki, Cheyenne, Lily, Natalie, Jace, JJ, and soon-to-be Mackynzie. He also leaves 5 sisters, Paula (Keith) Robert, Constance (Timothy) Neil, Kathleen (Mario) Domingos, Patricia (Steven) Lamagdeleine, and Elizabeth Butler, as well as several nieces, nephews, aunts, uncles, and cousins. His “brothers” in this life were his fellow correctional officers; especially Andrew, Larry, Paul, Karl, and Jesse, who risked their lives to save his during an inmate riot 26 years ago. Having a second chance at life, Chet lived to the fullest and was happiest when spending time with family and friends. Friendships were a cherished part of his life. He loved car races, his dogs, and concerts; its was fitting that his last adventure was a concert with one of his best friends. He was a deeply devoted father and grandfather and counted these among his greatest blessings in life. His love, friendship, and guidance will be missed eternally. At his request, services will be private and held at the convenience of the family.