Diane L. Simpson

Diane Simpson was born on December 30, 1944, in Glens Falls, New York, to Helen and Dan France. She grew up in Warrensburg, New York — a small town she loved all her life — where she later raised her family before moving to Old Lyme, Connecticut, in 2000 to be closer to her children and grandchildren.

Diane was predeceased by her parents and her brothers, Dan and Richard France. She leaves behind her two beloved daughters, Kelly Angelini and her children, Maria (23), Luca Angelini (20), Jack Mathews (10), and Mae Mathews (8); and Tiffany Kleefeld, her husband, Kurt Kleefeld, and their children, Harrison (19) and Jillian (16). Her family was the center of her world, and she cherished every moment spent with them.

For years, Diane worked ten- and twelve-hour days as a clerk and cashier at the Grand Union in Warrensburg. She knew her customers by name and greeted each one with a smile, a word of gratitude, and a warmth that made an ordinary errand feel like a visit with a friend. Having grown up with little herself, she never forgot it: at the end of a long shift she would gather the good food that might otherwise have been discarded and quietly bring it home to share with family and with neighbors who had even less. It was a small, steady kind of generosity, repeated day after day, and it said everything about who she was. Diane also helped support the early years of her daughters' companies, the France Foundation and Simpson Healthcare, lending administrative and travel support, and she was very proud to have been part of building them. The strong work ethic and values she lived by were not lost on those around her; she instilled them in her daughters, Kelly and Tiffany, and in her grandchildren from a young age.

Diane was a loyal friend who valued the relationships she built throughout her life. She was a gifted crafter with a special talent for decorating, and she took great pleasure in making every holiday feel special — especially Christmas. Each year she made wreaths: for her own home, as gifts for others, and to sell for a little extra. She also loved to bake Christmas cookies and share them with everyone she could. Her home and holiday decorations reflected the joy she found in creating memorable moments for the people she loved. She loved it all — the decorating, the baking, the giving, and most of all the white lights.

Diane's true passion, however, was watching her grandchildren grow up. You could always find her at school events, sporting events, and other activities, cheering them on from the sidelines. She was their biggest fan, their constant supporter, and one of their greatest sources of encouragement. Nothing brought her more happiness than being part of their lives and watching them grow.

She will be deeply missed by all who knew and loved her.

A mass of christian burial will be held on Saturday, November 14, 2026 at 10:30am at Our Lady of Sorrows Church, 14 Prospect St, Essex, CT 06426.