Alice Mary Cunningham (née Dooling), of Milford CT, passed away peacefully on Saturday, June 14, 2025

Alice Mary Cunningham (née Dooling), a lifelong resident of Milford, Connecticut, passed away peacefully on Saturday, June 14, 2025, surrounded by the love of her family. She was 92.

Born on May 8, 1933, in Milford, Alice was the daughter of Ruth and Patrick Dooling. She grew up in the Walnut Beach neighborhood, where she formed cherished memories that stayed with her throughout her life. She was predeceased by her beloved husband, John E. Cunningham (Jack). High school sweethearts, she and Jack shared 62 wonderful years of marriage and made a perfect team—devoted to one another and to the family they built together.

Alice’s life was centered around her family. She was a loving mother and a deeply devoted grandmother, finding her greatest joy in spending time with her grandchildren. She was known for her warm hospitality, and no family gathering was complete without one of Alice’s delicious home-cooked meals—she insisted on preparing each person’s favorite dish, which often resulted in a very crowded table featuring many courses. Just when you thought you couldn’t eat another bite, she’d smile and say, “You hardly ate anything!” Her home was a place of comfort, laughter, and great conversation.

Gift-giving was her love language and Christmas was her Super Bowl. Her grandchildren would all agree she always outdid Santa. She had a flair for fashion and a great eye for picking out just the right thing. Whether for food or clothes, shopping was one of Alice’s favorite pastimes and she loved driving out to the shops on the Post Road. She informed all her grandchildren of the latest trends.
Alice’s motto was to “go with the flow,” and she lived it with grace. She was an excellent conversationalist—always up to date on current events, the news, and, without fail, the weather. If you needed a forecast or a headline, you could count on Alice. She had a kind word and a compliment for everyone, and people were drawn to her warmth and trustworthiness. She listened without judgment and kept every confidence close.

She worked part-time for many years in the Milford school system, where she enjoyed supporting students and being part of the community. She was also a dedicated volunteer with the Milford Hospital Auxiliary for many years, graciously serving on the juice cart and offering friendly smiles and conversation to patients and staff alike.

Alice had a gentle love for animals, especially dogs, a fondness she shared with Jack.
A woman of lifelong faith, Alice was a devoted Catholic who found strength in her beliefs and persevered through difficult times with quiet resilience. After losing her husband, she lived independently for many years—an inspiring example of grace, strength, and good humor.
She cultivated deep friendships throughout her life. We were always amazed by the number of birthday cards she received every year. She kept in touch with so many people, and so many kept in touch with her.

Alice will be remembered for her kindness, her calm presence, and her uncanny ability to make everyone feel seen, valued, and at home. She leaves behind a legacy of love, generosity, and a life beautifully lived—carried forward in the hearts of all who knew her.

She is survived by her sons, Kevin (Cheryl) West Simsbury and Mark (Gayle) Glastonbury; her beloved grandchildren, Caitlin, Meghan, David, Allison Hobbs (Dan), Kyle, and Matthew; her great-grandson, Liam; and her sister, Patricia Dooling (Milford).

Besides her husband, Alice was also predeceased by her infant son, Craig; her sisters, Ethel and Ruth and brother John. Aunt Alice will also be missed by a host of nieces and nephews.

A Mass of Christian Burial will be celebrated on Saturday, June 21, 2025 11am at Saint Mary Church (Precious Blood Parish) 70 Gulf St., Milford, CT. Friends and family are invited to call from 9:30am to 11am AT THE CHURCH. In lieu of flowers, donations may be made to a charity of choice. To leave online condolences, please visit www.codywhitefuneralservice.com