Richard F. Pickering, 89, a longtime resident of Wingdale, NY, died on Monday, October 12, 2020 at Vassar Brothers Medical Center in Poughkeepsie, NY. Mr. Pickering worked as a therapy aide at the Harlem Valley Psychiatric Center in Wingdale and later worked in the Sign Maintenance Department at the NYS Department of Transportation in Patterson, NY.

Born on April 30, 1931 in Ellenburg, NY, he was the son of the late Orin and Nora (Houle) Pickering. On June 16, 1949 in Ellenburg Depot, NY, he married Lucille LaPorte who died on September 4, 2019.

Mr. Pickering organized and was the band leader for many years of the Hilltones Country Band which were noted as the best in the area. He also ran country music shows. He was a parishioner of St. Charles Borromeo Church in Dover Plains.

Mr. Pickering is survived by three sons, Randall Pickering and his wife, Sandra, of Gowanda, NY; Russell Pickering and his wife, Terry, of Wingdale, NY and Richard T. Pickering and his fiancée, Michelle Podbielski; a daughter, Diane Caza of Clinton Corners, NY and a sister, Teresa Bosley of Dannamora, NY. He is also survived by three grandchildren, Jason and Samantha Pickering and Michael Pickering and his companion, Katia Ellingsen and five great grandchildren, Jeremy, Skyla, Amelia, Gavin and Jackson Pickering.

Besides his parents and wife, he was predeceased by a son-in-law, Richard Caza, five brothers and five sisters.

Calling hours will be held from 4 to 7 p.m. on Thursday, Oct. 15, 2020 at the Hufcut Funeral Home, 3159 Route 22, Dover Plains, NY. Funeral services will take place at 9:30 a.m. on Friday, October 16, 2020 at the funeral home. Burial will follow at South Dover Rural Cemetery in Wingdale, NY. For directions or to send the family an online condolence, please visit

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