Chester was a graduate of Deep Creek Jr. High School. He was the owner of Chester Jr. Farm along with his wife and had also worked for the Sanitation Dept. of Baltimore County, World Wind Car Wash, Backriver Exxon Station and Backriver Supply Co.  He was a member of Whaleyville Methodist Church, Delmarva Poultry Industry, Farm Bureau, Chincoteague Pony and Horse Association, International and National Goat Association, and AMSA.

Chester loved God, nature, people and loved his wife dearly. 

Along with his wife he is survived by two step-sons, Thomas Shockley Cropper, Jr.  and his wife Tina of Hebron and Robert “Craig” Cropper and his wife Tammy of Powellville; a step-daughter, Virginia Jane “Ginger” Warren and her husband James Edward of Berlin; a sister, Myrtle Dickerson and her husband Owens of Baltimore; a brother, Clarence Chester and his wife Nettie of Baltimore; two nieces, Violet Chester and Miranda Brown; and a nephew, Owens Dickerson, Jr.; step-grandchildren, Rebecca Warren Timmons and her husband Kevin, James Brian Warren and his wife Rachel, Thomas Shockley Cropper, III, Shannon Lynne Cropper and Patricia Mae Cropper; one step-great grandchild, James David Warren.   He was preceded in death by his former wife Dorothy Weinhold and a brother Earl William Chester. 

In lieu of flowers donations may be made to Coastal Hospice, PO Box 1733, Salisbury, MD 21802 or Whaleyville United Methodist Church, 11716 Sheppards Crossing Rd., Whaleyville, MD 21872 or Dale Cemetery c/o Mr. Herman Truitt, 11571 Dale Rd., Whaleyville, MD 21872.