Andrea Jeanette “Ann” Simpson was born on April 22, 1942, in San Fernando, Trinidad & Tobago, to Eloise Clarke and George Clarke. She peacefully departed this life on February 28, 2026, at the age of 83.

Andrea spent her early years in the beautiful islands of Trinidad & Tobago, where she met her husband, Rudy Simpson. During their time in Trinidad, they welcomed their first two sons, Neil and Adrian. Shortly after relocating to Boston, Massachusetts, they welcomed their third son, Richard Simpson. Andrea eventually built her life in Boston, where she lived for most of her years while always maintaining a deep connection to her island roots, traveling back often. She carried the strength, warmth, and rich culture of her homeland with her wherever she went.

A woman of remarkable class, patience, and quiet strength, Andrea was known for her elegance and calm presence. Her voice never needed to be raised to be heard. She moved through life with grace, dignity, and a quiet authority that naturally commanded respect. Those who knew her understood that her strength was not loud, but deeply felt.
Andrea built a meaningful and dedicated career while raising her family with love and commitment. She worked for Allstate Insurance for more than 25 years, where she was known for her professionalism, reliability, and strong work ethic. After many years of service there, she continued her career at Quincy Mutual and later at the Registry of Deeds, where she worked until the later years of her professional life. Throughout it all, Andrea balanced work and family life with grace while raising her three beloved sons: Neil, Adrian, and Richard Simpson. Her home was one filled with structure, love, and tradition.

Faith was at the center of Andrea’s life. She was deeply involved in her church and community, and her faith remained unwavering throughout her life. She often reminded those around her that “prayer is power.” Her spiritual strength guided her through life and inspired those around her.

Andrea found her greatest joy in her grandchildren and great-grandchildren. She took immense pride in supporting and being present in their lives, attending school events, celebrations, and many important milestones. She loved being surrounded by family and especially cherished the laughter and energy of young children. Hosting gatherings and bringing family together was something she did with love and intention. One tradition her family fondly remembers was Granny making a stop at the McDonald’s drive-thru—a small but cherished memory that brought smiles to many.

Andrea was known for her incredible patience and wisdom. She listened deeply and thoughtfully, always keeping the best interests of others at heart. She was an early riser who believed in getting things done and living life with purpose. When she spoke, she only needed to say something once—her words carried weight and meaning.

Visitation will be held at the Dolan Funeral Home, 1140 Washington Street, DORCHESTER LOWER MILLS ON Wednesday, March 11, 2026, from 6 -8 PM. A Mass of Christian Burial will be celebrated at Our Lady of the Visitation Parish (Saint Mary of the Hills Church), 29 Saint Marys Road, MILTON on Thursday, March 12, 2026, at 10 o'clock. Interment Milton Cemetery. Relatives and friends invited.