Kathryn Dileo

Kathryn Dileo obituary, Winsted, CT

Kathryn Dileo

Kathryn Dileo Obituary

Obituary published on Legacy.com by Montano-Shea Funeral Home - Winsted on Nov. 21, 2025.

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Kathryn (McCann) Dileo
October 21, 1924 – November 13, 2025
BARKHAMSTED –
Kathryn (McCann) Dileo, 101, passed away peacefully at her home on Thursday, November 13, 2025, accompanied by her devoted nephew, Shawn Frederick Newman. She was the beloved wife of the late Pat Dileo, with whom she shared 37 years of marriage.
Born on October 21, 1924, in New Hartford, Kathryn ("Kate") was the daughter of the late George and Elizabeth (Decker Kilmer) McCann. After the passing of her father in 1926, Kate was lovingly raised by her mother, Elizabeth, who instilled in her the values of care, generosity, and devotion that would define her life.
Kate attended the North End School in New Hartford, lived through the historic flood of 1955, and worked for the Gilbert Clock Company in Winsted, and the Underwood Factory in New Hartford. She diligently assisted her husband Pat with his growing catering business, by cooking and preparing countless pans of dinner food, trays of sandwiches, baked goods and much more - in their home at first, then later at Dileo's Grove Banquet Hall in Torrington. Later in life, she worked at Marshalls in Avon alongside her sister Marion and niece Diane-times filled with laughter and companionship. Kate shared a special and close friendship with her sister Marion.
Kathryn's natural gift for care giving touched many lives. Her greatest joy was caring for others-children, siblings, elders, and friends. Alongside her mother, she helped raise her nephew Anthony and niece Diane. Other nephews and nieces spent summers with Kate and her mother, Elizabeth. Over the years she also tenderly cared for a brother, her mother, her sister, her nephew and her husband during their final seasons of life. Her ability to offer comfort, dignity, cleanliness, nurturing, and presence was one of her defining qualities.
Above all, Kathryn treasured her family. Her home on Holcomb Hill Road was a gathering place-warm, busy, and always open. Visitors were met with a meal, a cup of coffee, ice cream and cookies, a soda pop, or simply the unmistakable feeling that they were cherished. She made everyone feel like family.
She stayed close with her nephew Raymond Caine of Indiana and niece Verna Jean (Suiters) Wagner and husband Tim of Tennessee, as well as her many grand-nieces and grand-nephews, great-grand-nieces and great-grand-nephews, and great-great-grand-nieces and nephews-each of whom she treated as if they were her own.
She leaves behind her dear nieces-in-law: Rosemary Caine of New Hartford and Joan Caine of Barkhamsted; and her beloved grand-nephews and nieces: Shawn Frederick Newman and wife Susan of New Hartford; Elizabeth (Newman) Marek and husband Edward Ligouri of Bakerville; Lucinda Newman of Vermont; Ann Marie (Casciani) Roarke of Canaan; Allison (Casciani) Williams of Norfolk; and Anthony Casciani of New Hartford, along with many more extended family members whom she loved deeply, including her in-law nephews, Gary Dileo and Joey Dileo.
In addition to her parents and her husband, Kathryn was predeceased by her siblings: Raymond "Slim" Kilmer, Dorothy (Kilmer Caine) Suiters, Chester "Chet" Kilmer, Leslie "Let" Kilmer, and Marion (Kilmer Casciani) Hughes; her nephews Anthony "Junior" Casciani and wife Joanie, Norman Caine, Jim "Sonny" Caine, Myles Caine, and Ronald Caine; her nieces Barbara (Caine LeGeyt) Noak and Diane (Caine Newman) Marek; and her grand-nephew Myles "Hiver" Caine, Jr.
Graveside services and burial will on Saturday, November 22, 2025 at Village Cemetery in New Hartford at 10 AM. Montano-Shea Funeral Home is assisting the family with arrangements. To share memories or offer condolences, please visit Montano-Shea.com. In lieu of flowers, donations in Kathryn's memory may be made to Hartford Healthcare at Home Hospice: 1-800-HOMECARE (1-800-466-3227)
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