Robert M. "Bobby" Caiola
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Robert M. "Bobby" Caiola

Milford - Robert M. "Bobby" Caiola, 75, of Milford, DE formerly of Walton, NY passed away peacefully on Monday, February 15, 2021 at Bayhealth Sussex Campus. He was born in Bayshore, NY, the son of the late Samuel Caiola and Annabelle McMann. Throughout his life, Bobby was a jack of all trades and was an accomplished tradesman with a knack of perfecting whatever projects he was working on. He was a residential maintenance mechanic, electrician, machinist, a commercial diver, underwater welder and marine salvage specialist. Bobby enjoyed being an active member of the community whether it be in Walton, NY or Milford, DE, for he loved unselfishly giving of himself to assist others. He enjoyed being able to help anyone who was in need and he felt the way to do that was to participate in his community. Bobby loved to cook and even took a culinary class at Del Tech just for something to do. He was a member of Carlisle Fire Company, Milford, DE; the Walton Fire Company, Walton, NY; the Boy Scouts of America, where he served as an assistant scout master and taught advanced leadership training; a member of the Lawdogs LE/MC (made up from Law Enforcement Agencies, Firefighters, EMTs, and our Military Service men and women), and the Milford Elks Lodge # 2401. In his spare time, Bobby enjoyed doing leather work, riding motorcycles, was an avid collector of junk and was an A-1 Hoarder (with everything chronicled and stacked accordingly.)

Bobby is survived by his wife of 38 years Debra Caiola; two sons Billy Caiola and his wife Kristin and Jimmy Caiola and his wife Alex; two daughters Dawn Bonfiglio and her husband John and Bobbie Jo Ellefson and her husband Mark; four grandchildren Samantha, Leighann, Melanie and Joey; and one great grandson Robby.

A visitation will be held from 11 am to 1 pm on Saturday, February 20, 2021 at the Carlisle Fire Company, 615 N.W. Front Street, Milford where services followed by firefighter honors will be held at 1 pm.

Services will be live streamed. Please keep an eye out on our website with an update on what platform the live stream services can be found online.

In lieu of flowers, the family suggests contributions be made in Bobby's honor to the Delaware Humane Association, 701 A Street, Wilmington, DE 19801, Attn: Jeanette Hayes. Arr. by Lofland Funeral Home, Milford, DE. Letters of condolence may be shared with the family at

To Plant Memorial Trees in memory, please visit our Sympathy Store.
Published in The Daily Times from Feb. 17 to Feb. 18, 2021.
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February 18, 2021
My deepest sympathy to the Caiola Family for the loss of your loved one, Robert, "Bobby", and pray God gives you comfort, peace and strength.
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