Dorothy Ellen Bruce Underwood of Oak Bluffs died peacefully at home on Sept. 20, 2026, at 99. It will come as no surprise to those who knew her that she authored this obituary.
Born to Viola and Charles Bruce in Somerville, Dorothy was the fifth of seven children. Her mother died when Dorothy was 3. In her twenties, Dorothy worked in a sewing factory on Kneeland Street in Boston. She later became a bookkeeper, having a knack for numbers.
She met David Underwood, the love of her life, in the mid-1950s, when he played Monopoly with her upstairs neighbors. Their relationship blossomed, but soon David was called up to serve in the Army and stationed in Germany. After two years apart, he returned home, and their courtship resumed.
Dorothy and David married on Valentine’s Day, Feb. 14, 1960. Before leaving for work the day after their wedding, David promised to always take care of her — and he did. They raised their children in Randolph and Oak Bluffs, furnishing their homes one room at a time.
Dorothy loved to sew, making clothes for herself, her daughters, and their dolls. She made slipcovers, draperies, and window shades. She taught herself to wallpaper, paint, refinish floors, and lay carpeting and linoleum. A homebody by nature, Dorothy was happiest caring for her family and home.
Dorothy first visited Martha’s Vineyard in 1934, when she was about 7 years old, with a family friend who lived down the street in Roxbury. They attended Illumination Night. Thirty years later, she and David bought a house in Oak Bluffs with no plumbing or electricity. They brought supplies in a station wagon over the years, including a bathtub, kitchen sink, lamps, and a hand-me-down refrigerator from David’s mother. Always a team, they worked on the house together. Dorothy painted around the windows, while David painted the walls. He mixed wallpaper paste, and held the ladder while she hung the wallpaper. He dug in the garden, and she planted.
David died in 2021, and Dorothy’s health began to decline shortly afterward. She is survived by her daughters, Michelle Tyndal of Hawaiʻi, Jennifer Thomas (David Thomas) of Maryland, and Melissa Perry of Milton; grandchildren, Joshua Somoano (Heidy), Rebecca Thomas, Lydia Perry, Jared Thomas (Emily), and Joey Perry (Sage); great-grandchildren, J.J., Julissa, and Reign; and many nieces and nephews.
Dorothy was grateful to her “special angels”: sisters-in-law Gretchen Tucker Underwood and Laura Underwood Horne; brother-in-law Emmanuel Horne; nephew Peter Wharton; and dear friends Debbie Stead, Ann Baird, and Joanie Oliver.
In lieu of flowers, please consider making donations to two organizations that played such important roles in her life: the Oak Bluffs library (online at bit.ly/OBPL_Donate), whose amazing staff so generously supported her love of reading, and Hospice and Palliative Care of Martha’s Vineyard (online at hospiceofmv.org/annual-appeal), whose staff provided such skilled, loving, and compassionate care at the end of her life.
A celebration of the lives of Dorothy and David Underwood is planned for summer 2027.
