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Wilbur Wayne Gregory | 72 | Winchester

Wilbur Wayne Gregory, 72, of Winchester, passed away Sunday morning Nov. 13, 2022 at his home. He was born February 1, 1950 in Jacksonville the son of the late Kenneth J. and Roberta Ryan Gregory. He married Susan Buchanan Sept. 25, 1971, they later divorced.

He was a 1968 graduate of Winchester High School. He served in the US Army serving in Viet Nam. He had worked for Oscar Myers for many years, the City of Pittsfield Water and sewer dept., and was currently employed with West Central Mass Transit. He loved the outdoor life and looked forward to deer hunting season every year, fishing, raising cattle, visiting with friends and thoroughly enjoyed watching his grandson Tyler play basketball.

Surviving are his children, David (JeanAnn) Gregory of Auburn, and Amy Gregory (Freddie Andrews) of Winchester, grandson Tyler, brother Kenny (Diana) Gregory of Pittsfield, sister Cheryl Drake of Winchester and many nieces, nephews and cousins. Preceding him in death were his parents, infant brother David and sister Susan, and his brother-in-law Rod Drake.

A funeral service will be held at 10:30 am Thursday, Nov. 17, 2022 at the Coonrod Funeral Home in Winchester. Burial will be in Winchester City Cemetery where military honors will be conducted. Visitation was held on Wednesday from 5 until 7 pm at the funeral home. Memorials can be made to the Winchester American Legion or to the family. Condolences may be sent to the family at

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