William "Bob" Willoughby Jr.

William R. "Bob" Willoughby, Jr
April 29, 1942 - August 25, 2025
Bob Willoughby, 83, passed away peacefully on August 25, 2025. Bob was born in Halifax County, NC and grew up in Conway, NC. He attended Conway High School, Chowan College, and graduated from Frederick College in 1968. He married the wonderful Diane in 1966 and ultimately moved to Virginia Beach where he lived the rest of his life. Bob also served in the Navy Reserve for six years.
Bob was predeceased in death by his wife, Diane W. Willoughby, his mother, Ethelyn Willoughby and father, William R Willoughby, Sr. He is survived by his daughter, Kimberly Willoughby Harper (Eduardo Trinidad), his two grandsons, Logan and Landon Harper, and his three grandchildren, Rayna, Quinten, and Mykah Trinidad; his sister, Betsy Freuler, and nephews Bobby and Ben Freuler, and Chad Whitley who he always called "my boy", as well as numerous members of his extended family and friends. Bob loved his family and friends dearly.
Bob worked for the Virginia Department of Health (Chesapeake) for 36 years before retiring to start his beloved Soil business.
In his spare time he coached girls softball at Azalea Little League in the 70's, played slow pitch men's softball for years well into his 50's, had a firewood business, was an avid gun enthusiast including decades in the North South Skirmish Association shooting his muskets, and was a well known Billiards player being inducted into the Hampton Roads Billiards Hall of Fame in 2015. Bob loved playing golf and hit a hole-in-one at Red Wing in 2018.
His greatest achievement was his beach house on Hatteras Island that he personally built with his best buddy, Robert, weekend warriors for a year or more. The house is still standing and beautiful and enjoyed by friends and family every summer.
Bob had a wonderful and eventful life and he lived it to the fullest. He is going to be missed by so many people. A Celebration of Life is being planned and a public notification will be made once the memorial has been scheduled.