Jane S. Leonard

Jane S. Leonard, 76, of Deep River, CT, died at her home on January 30, 2025.

Jane was born on March 8, 1948. She grew up in Rockland, MA in the home of her late parents Ernest and Dorothy Chekoulias. She attended Holy Family School and Cardinal Spellman High School before continuing her education at Bridgewater State University and the University of Chicago.

She is survived by her devoted husband of 54 years, Edward F. Leonard, originally of Abington, MA; her married children, Daniel and Leonor Leonard, David Leonard and Christine Saari, and Alissa and Nate Fowler, her five cherished grandchildren, Nico (13), Oliver (10), Grayson (7), Diego (2), and Winter Jane (1); her siblings, Judy Chekoulias, Cindy Chekoulias, and Scott Chekoulias, Anita Drapeau, her niece Kate Drapeau and son Jack, her nephew Michael Drapeau, his wife Caitlin and son Henry.

Jane and Ed raised their family in a warm and loving home in Hubbardston, MA for nearly 45 years. She had an extraordinary gift for making a house a home. She and her daughter, Alissa, spent years together showing Morgan horses, a passion that brought them great joy.

Jane’s love of literature shaped her life and career. She worked at the Worcester Art Museum and Nathan Greenberg & Associates before becoming a dedicated educator at Mount Wachusett Community College in Gardner, MA. There, she taught reading and writing to ESL students, caring deeply about them as individuals and always encouraging their voices to be heard. She shared her passion for books with everyone in her life, always engaging in vibrant discussions about literature with family and friends.

A lifelong love of summers “up at the lake” began in her childhood at Lake Waukewan. Later, she created a beloved summer tradition at Squam Lake, where she could often be found soaking up the sun on the dock or headed barefoot “ta da beach” with a grandchild in tow. Jane also loved traveling with close friends, forming lifelong friendships that brought her immense joy.

In her later years, Jane moved to Deep River, CT, to be near her grandchildren. Affectionately known as “Gigi”, she was a loving and always present grandmother. Deeply involved in each child's life, she celebrated every moment with them and every milestone along the way. Her family was her greatest joy, and she was theirs. Gigi nurtured them with the same warmth and care that she brought to every part of her life.

Gigi was a most extraordinary woman. Endlessly kind and caring, she leaves us a legacy of thoughtfulness and warmth. She will be profoundly missed by all who had the privilege of knowing and loving her.

A wake will be held at McDonald Keohane Funeral Home North, located at 40 Sea St, North Weymouth, MA on February 6 from 4-7 pm. A Remembrance Service will be held at Tosca in Hingham, MA on February 7 at 11am. 

If you would like to make a donation in Jane’s honor, please consider your favorite charity or The Dr. John F. McEwan Memorial Scholarship at Cardinal Spellman Central High School. John was a dear friend of the family. https://www.spellman.com/support-spellman/endowment-scholarship

*If you would like to place an order of flowers in loving memory of Jane, the family requests all flowers are neutral (whites / greens) and pastels (pinks)*