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Official Obituary of

Dorothy Helen (Zombeck Tomaskovic) Oakley

September 19, 1929 ~ September 26, 2023 (age 94) 94 Years Old
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Dorothy Oakley Obituary

Dorothy Helen (Zombeck Tomaskovic) Oakley passed away on September 26th2023, at NY-Presbyterian Hudson Valley Hospital in Peekskill, after a short but valiant battle with pneumonia. She had just turned 94 years old one week before.

Dorothy Oakley was born in the Bronx in 1929 to Martin and Sophie (Ceglecki) Zombeck. As a child she lived in Peekskill NY and Yonkers, NY, graduating from Commerce High School with a focus in secretarial skills. She met her first husband, Edward Tomaskovic (1928-1987), while they were both employed by the Alexander Smith Carpet Factory in Yonkers, and they married in 1950. After 4 of their five children were born, they moved in 1960 to Brewster, NY, where Dorothy volunteered at her children’s school, St. Lawrence O’Toole. She worked at the Brewster Public Library, and as the Brewster village clerk. She was very active In the local Republican Party. In the early 1980s she moved to Port Chester and began working at IBM, where she was an executive secretary. Dorothy met her 2nd husband, Harry Oakley, on a cruise through the Panama Canal. They married in 1991, and she moved to his home in Murrell’s Inlet, South Carolina, where she became an active member of St. Michael’s Catholic Church in Garden City, as a Eucharistic Minister and Lay Franciscan, and volunteered in Georgetown, SC. Dorothy and Harry traveled to many countries and to many parts of the United States. Her final 20 years of life were complicated by multiple medical difficulties, from a brain tumor to a broken hip to a brain injury to a seizure disorder to loss of hearing to a serious lung infection. She and Harry moved in 2011 to Ossining, NY, near her eldest son John, and when Harry entered the VA nursing home in  Montrose, Dorothy moved to Drum Hill Senior Living Center in Peekskill, just a few blocks from her son, Peter, as well as very near the house she had lived in as a child.

Dorothy loved music and dancing, and reading, especially about history. She took numerous college classes as an adult, as she enjoyed learning new things. She was a terrific cook, and a loving mother and grandmother. Her kids remember that she always cooked them a hot breakfast before school. She loved traveling and taking care of her husband, Harry. Among her favorite trips was the 50th anniversary of D-Day tour, which took them to numerous countries. She especially loved tours that included educational lectures. Another hobby was genealogy; it allowed her to indulge her love of family. She adored her aunts, uncles and cousins, and shared her findings with them at cousin gatherings and the family reunions she organized. A very social person, Dorothy threw lots of dinner and other parties. She typed up Harry’s memoirs of his years as a pilot during the 2nd World War and afterwards, and did the same for some of his old Army Air Corp buddies. She was a fan of the Brooklyn Dodgers, whom her uncles had taken her to see while growing up.

Dorothy was predeceased by her brother Martin Zombeck, PhD; two husbands; and her grandsons Eric Tomaskovic and Timothy Tomaskovic. She is survived by her sister, Barbara (Zombeck)Hayduk, sisters-in-law Monique (Lagouthe) Zombeck and Margaret (Tomaskovic) Kucharczyk, and brother-in-law Friar Emil Tomaskovic of Graymoor; her children John Tomaskovic (Dorene) of Ossining NY, Peter Tomaskovic (Patricia) of Peekskill NY, Barbara Tomaskovic-Devey (Donald) of Montague Massachusetts, Stephen Tomaskovic (Linda) of Bloomingdale New Jersey, and Paul Tomaskovic(Michelle) of Forest Hill Maryland; grandchildren Christopher John Tomaskovic, Sarah Lanigan, and Beth-Anne Kiernan; Anna Rapp and Nicholas Tomaskovic-Devey; Christopher Tomaskovic; Jayson and Mathew Tomaskovic; Michael, Edward and Andrew Tomaskovic; step-grandchildren Amy Bennett-Laydon (John) and Aaron Bennett; great-grandchildren Molly, Aislinn and Brendan Lanigan; Mickey and Sadie Kiernan; Arthur and Hannah Rapp; Amelia, Jack and Claire Laydon; plus a number of cousins, nieces and nephews. Arrangements are being made by the Leach & Thomas Funeral Home in Ossining. Funeral Mass, Saturday, October 28th, at the St. Francis Convent Chapel, at the motherhouse of the Franciscan Sisters of the Atonement at Graymoor in Garrison.


45 S. Highland Ave

Ossining, New York 10562


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Funeral Mass
October 28, 2023

11:00 AM
St. Francis Chapel at Graymoor
40 Franciscan Wat
Garrison, NY 10524


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