In Memory of




Obituary for Ann May (McCauley)

Ann McCauley May
8 January 1934 - 10 October 2023

Ann McCauley May died suddenly on Tuesday, October 10th, while recovering from a recent illness. She was 89 years old.
Born on January 8, 1934, she was the third daughter of Joseph T. and Lillian Thompson McCauley, and lived in Winchester for most of her life. She was preceded in death by her devoted life partner and husband of 62 years, William F. May Jr., and her sisters Ellen McCauley-McGarty and Susan M. Connolly.

Ann May was born and raised in Winchester and could point to four homes in town to which she had a connection. She raised five children in the 1960s and 1970s; for that alone, she deserves a medal. As a girl, she attended Camp Asquam in Squam Lake, N.H., each summer. She was educated at the Newton Country Day School of the Sacred Heart, went on to Garland Junior College, and then worked in Boston. In early 1958, she met Bill May while skiing at Cannon Mountain in Franconia, N.H., and they were married within the year. The newlyweds lived briefly in Taunton, bought their first
home in East Walpole, and moved to Winchester in 1965. The Mays also enjoyed a summer cottage in Mattapoisett for more than five decades.

Ann May was a fine athlete, an excellent skier and tennis player. She was also a school and community volunteer, a board member at the Mt. Vernon House in Winchester, worked with a Winchester friend for Mystic Valley Traders, and enjoyed a slower pace with her husband and neighbors in later years. She was a social person right until the end, enjoyed being with her family and friends, and was the legendary winner of a neighborhood Super Bowl pool one year – the food and party being much more interesting than the game.

In recent days, though she was not feeling her best, her spirits were remarkably strong and positive. She was heard to say a number of times, just this past weekend, “Isn’t it wonderful?” To the last, Ann May was a true and dignified lady: mannerly, friendly, sweet, proud, and strong. The last three or more years were hard for her, yet she accepted her challenges and was gracious even in her final days.

Surviving are her children Julie May Daniels and her husband John (Hopkinton, N.H.), Alexander May and his wife Sheila (Melrose), Peter May and his wife Sandy (Hinesburg, Vermont), Timothy May and his wife Carolyn (Malden), and Sarah May Clarkson and her husband Kris (Pocatello, Idaho) and nine grandchildren: Sarah, Ben, and Annie Daniels; Natalie and Aidan May; Jacob and Elizabeth May; and Joseph and William Clarkson. In addition, there are numerous nieces and nephews on her side and her late husband’s side of the family.

The family wishes to thank the staff at Sunrise of Arlington for the community and friendship they provided to our mother, and in particular to Richard, her best companion there; to Nursing on Demand for the care they have taken with our mom since 2020; and to David and Ivan who provided love and support to our parents in their home.

A funeral mass of Christian burial is scheduled for Monday, October 16, at 11 am at St. Mary’s Church, 155 Washington Street, in Winchester, the church in which Ann and Bill May were married in 1958. The family will be glad to meet visitors at Lane Funeral Home, 760 Main Street, Winchester, at 10 am, before the funeral. Immediately following the church service, the burial will proceed at Wildwood Cemetery, 34 Palmer Street, in Winchester.

In lieu of flowers, the family would encourage people to make contributions in memory of Ann May to the charity of their choice.