Harold L. Woodruff departed this life surrounded by loved ones on September 24, 2021. He was born in Petersburg, Indiana on August 12, 1938. He was the son of Lilburn and Lavonnah (Ainscough) Woodruff. He was one of eight children. Harold was united in marriage to Inez Fair on February 12, 1959 and is survived by his loving wife of 62 years. Mr. Woodruff is survived by his children. Rem (Marilyn) Woodruff of Effingham IL, Rue (David) Telford of Damiansville IL, Rae (Andrew) DeLao of Salem, Ria Woodruff of Aurora CO, and Ryan Woodruff of Salem. Grandchildren Matthew Cathcart, Lindsey Cathcart, Hannah DeLao, and Zachary Telford. One great grandchild Malcolm Cathcart. Siblings Marilyn (Jim) Puckett, Robert (Marilyn) Woodruff, William (Cecila) Woodruff, Connie (Larry) Ingram, and David (Patty) Woodruff. Two brother in-laws Timm (Susan) Fair, and Kent (Lynette) Fair. Harold was preceded in death by his parents and siblings Sheldon (Theresa) Woodruff, and Twila (Bill) Donaldson. In-laws Remel “Shorty” and Mardell Fair. Daughter-in-law Vanna Andersen. He worked his way through SIU Carbondale and received a BA in Chemistry in 1960. In 1968 he received a Master’s in Guidance and Counseling from Eastern Illinois University. He began his teaching career at Odin High School. Later he taught Science, Math, and coached baseball at Buckley Community Schools. He was the chairman of the Math Department at Salem Community High School while teaching mathematics. Later he became a Guidance Counselor at SCHS, sponsor of the Student Council, Peer Helpers, 8th Grade testing, and Freshman Orientation. After he retired from SCHS he became a Guidance Counselor at Sandoval Grade School for 9 years. He also sold real estate for Century 21. Harold continued to tutor students in math after his retirement especially his grandchildren and their friends. Harold was an active member of Grace United Methodist Church in Salem. He was the church Treasurer, Chair of the Memorial Committee and served on various committees. He was a past member of the Salem Elks and Lions Club. He enjoyed playing golf and was a member of the Salem Country Club. He enjoyed playing Bridge with his friends. He loved boating and spending time with his family and friends on the lake. Harold was also very interested in genealogy where he traced his family history back to the 1400’s. He was known around town for daily walking his dogs. He also enjoyed gardening and planting flowers. Services will be held on Tuesday, September 28, 2021 at Grace United Methodist Church, 116 E. Schwartz, Salem. Visitation will begin at 9:30 a.m. with the service following at 11 a.m. with Pastor Christine Cunningham presiding. Memorials can be made to Grace United Methodist Church or SSM Good Samaritan Hospice. Interment will be held at East Lawn Cemetery. Memorials can be left at Crouse Funeral Home in Salem who is assisting the family with arrangements. Online condolences can be left at www.CrouseFH.com or on the funeral home’s Facebook page. The funeral service will be recorded and available to view on the funeral home website following the conclusion of services.