Cathy Winchester

Violet Catherine “Cathy” Winchester passed away peacefully on June 12, 2026, leaving behind a legacy of love, friendship, service, and unwavering devotion to family and community.

Born in New York, New York, to Rose (Boyle) McGlone and Patrick McGlone, Cathy built a successful career as an insurance claims manager and was very proud of the fact that she finished her career as a vice president. She was known for her dedication, compassion, and ability to connect with people from all walks of life.

Cathy met the love of her life, Dennis Winchester, at a military picnic. Their connection was immediate, and they married within a year. Together, they shared 57 wonderful years of marriage. The couple made their home in New York for 32 years, where they became devoted advisors for the Dutchess County Catholic Youth Organization. Through their guidance, encouragement, and genuine care, they touched the lives of countless teenagers. Cathy affectionately referred to those young people as “their kids,” a testament to the lasting bonds they formed.

In 1999, Cathy and Dennis relocated to New Port Richey, Florida, where they continued to embrace life with enthusiasm and purpose. They remained active in local theater, a passion they shared for many years. Cathy especially enjoyed stage managing, attending theatrical productions, and supporting the arts. Together, they raised several beloved pet birds, including their current companion, Rosie.

Cathy's many interests included reading, theater, game nights, and sharing dinners with friends. Those who knew her well will fondly remember her signature beverage—a glass of iced red wine—and the warmth, laughter, and conversation that always accompanied her presence.

She is survived by her beloved husband, Dennis Winchester; her brother, Jack McGlone; her niece, Kerry (Michael) Manchester; great-nieces, Riley and Teagan Manchester; her nephew, Patrick McGlone; and two of her cherished “kids,” Maureen and Andy Irvin. She also leaves behind grandchildren Quinn (Jimmy) Zottoli and Jack (Matthew) Irvin, and great-grandchild Camden Zottoli.

Cathy leaves a lasting memory with everyone who had the pleasure of knowing her. She listened intently, laughed easily and often, loved fiercely, and gave generously of her heart. Her kindness, wisdom, and unwavering support enriched the lives of so many and will continue to be remembered by all who loved her.

In lieu of flowers, the family kindly requests that memorial donations be made in Cathy’s name to Metropolitan Ministries.

Eulogies:

Grandma,

I never imagined that life would play out this way. We were supposed to have more time to make new memories together. It never crossed my mind that there was a chance you wouldn’t meet Camden in person. I can still feel your hands on my pregnant belly last summer talking about “our girl.” I promise that our girl will know all about you, how fiercely and unapologetically you lived your life, how beautiful you were inside and out, and how much you loved us.

The evening after you passed, I poured myself a glass of red wine with ice in it, just how you liked it. A cardinal sat outside on the fence and I could feel you with me. I will forever be grateful that I had the blessing of being loved by you. I love you, and I couldn’t have asked for a better grandma. Our girl has the best guardian angel.

Your sweet pea,

Quinn

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I feel beyond lucky to have been loved by Grandma Cathy for my entire life. She and Dennis became a part of our family when they met my parents as teenagers long before my sister Quinn and I were born, and the second we came into the world they became our bonus grandparents. The fact that we do not share blood with Cathy and Dennis, and they chose to make us part of their lives, makes me exponentially more grateful for their love. I will forever cherish every moment we spent together — from trips to Florida and days spent at theme parks to learning about her deep appreciation for New York whenever she’d visit. The part of my bond with Grandma Cathy that is closest to my heart is how immensely supported she always made me feel. She kept up with everything I did growing up, called on my birthday every single year, celebrated my gay identity without a second thought and regularly read my work as a writer. She made me feel so important. I know she’s done the same for my family and so many other people in her life. Thank you, Grandma. I hope you can now look down and see the incredible impact you’ve made on all of us.

Love,

Jack

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Of all the people in all of the world. I got to meet Cathy and Dennis. I was 17 years old, involved in the Catholic youth organization in my local parish and started to get involved at the county level and Cathy and Dennis were advisors. I wish I could recall the exact moment we met but I can’t. I wish I could remember where we were but I can’t. What I can remember is Cathy’s laugh and her smile and the easy way she made everyone feel comfortable and important. I remember Dennis’s shenanigans and his slapstick comedy. He always found a way to make you laugh. And he still does! You knew right away after meeting them that they loved fun, they loved being around people (especially teenagers!) and they loved each other. They were a team and they welcomed all us kids with open arms and an open home.

I come from a great family. The middle of 5 kids. I was well loved but sometimes easily lost in the shuffle. I didn’t know I needed a second mom but Cath was always there for the teen that struggled through those teenage years. And she was there for me. And Dennis was always there supporting her - supporting us.

We never lost touch. For over 40 years - They have always been a part of my life. They welcomed my husband Andy so much that he asked them to be his godparents. Our children have always called them Grandma and Grandpa.

I came home one day from a drs appt(Cath was hanging with our daughter Quinn). The two of them were sitting in the driveway inside a chalk-drawn school bus singing together. It was at that moment that I truly thanked God for blessing my life with the gift of Cathy and Dennis.

Quinn, was born in Delaware. We moved back to NY shortly after that and our son Jack was born a couple years later. I’ll never forget the look on Cathy’s face when she walked into that hospital room and I put him in her arms and introduced Jacks to Grandma Cathy. The tears, the laughter, the pure joy … she said “you have no idea kid - how much I love you.”

Florida didn’t separate us. We made great memories all of us in their pool. Dennis being a goofball making our kids laugh so hard their tummies hurt. Going to Busch Gardens, the zoo, so many amazing memories. Our kids got to fly down and visit Grandma and Grandpa on their own. (Great Grandma Poppy to Camden. ) Cath loved to bend (really break) any “rules” that we may have had. And she loved to brag about it. And I loved that she did it. She had such an amazing bond with each of our kids.

I could go on and on. Lord knows the memories are on constant repeat in my head. I know I would not be the person I am today without Cathy and Dennis in my life.

Cath- you are always in my heart - and I can honestly say “because I knew you - I have been changed for good. “💜

Love you Poppy…

Maureen