Cover photo for James Edward Gregory Sr.'s Obituary
James Edward Gregory Sr. Profile Photo
1939 Jim 2023

James Edward Gregory Sr.

October 21, 1939 — February 28, 2023

James Edward Gregory Sr., 83 of Mount Airy, MD passed away peacefully Tuesday, February 28 in Columbia, SC due to injuries sustained from an auto accident.

Born, October 21, 1939 in Newton Grove, NC he was the son of the late Francis and B. Moselle (Johnson) Gregory.  In addition to his parents he was preceded in death by his brothers, Joseph Gregory, Francis Gregory Jr., Gerald Gregory, and Louis Gregory.

Jim started working at a very early age on the family farm running heavy equipment, planting crops and working in the fields. He attended  Dematha Catholic High School in Hyattstown. 

Jim was an entrepreneur, a visionary and innovator in everything he set out to do.  He started first by joining his father to work at their excavating company, F.E. Gregory and Sons.  He then moved forward to help establish the family-owned business of Digging and Rigging. He was there each day putting in long hours 6 days a week up until his death. He thrived working with his hands and believed in a good day of hard work was an accomplishment for anyone. 

Jim enjoyed many activities to include, going to the beach, riding his electric bicycle, horseback riding, restoring antique cars, making wine and homemade jam.  He would attend the Annual Frederick Fair and support the 4H clubs each year.  Jim was also an expert in BBQ, made his own sauces and would have given anyone a run for their money this side of the Carolina’s. 

He enjoyed traveling and went many places to include Europe and the Caribbean but especially loved going to Walt Disney World in Florida where he had just spent a beautiful family vacation prior to his death. 

Jim was a man of love and honor and held fast to his faith in Jesus Christ.  He carried his rosary with him each day and spent every Saturday evening in Church no matter if he was at home or traveling.  

Jim is survived by his loving wife of 62 years, Susan E. (Thomas) Gregory. 

Sons, James Gregory Jr (Pam) of Mount Airy, MD, John Gregory (Christy) of Emmittsburg, MD. David ”Wayne” Gregory (Anna) of Walkerville, MD. 

Grandchildren, Aaron Gregory (Jessie), Jessica Mcgaha (Mike), Breanna Gregory (Kyle), Collin Gregory (Danielle), Derrick Kinna (Cassie).  

Great Grandchildren, Camden, Aaron Jr, Saylor, Kaylee, and Gavin. 

Siblings, Ronald Gregory (Phyllis), Patricia Rice, Sharon Coburn, George Gregory (Karen), Angela Wenzel, Richard Gregory (Linda), M. Denise Early (Jeff), Stephen Gregory (Cecelia). Numerous nieces/nephews, cousins.  

He is also survived by his Digging and Rigging family whom he loved dearly, mentored, and touched so many of their lives. 

Funeral services will be private.

A celebration of Jim’s life will be announced at a later date. 

Arrangements are with Stauffer Funeral Home, Frederick.  Expressions of sympathy may be shared with the family at

To order memorial trees or send flowers to the family in memory of James Edward Gregory Sr., please visit our flower store.


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