Dorothy Ann Raymond, of Chatham, passed away on August 8, 2023, ending a long and fascinating life, marked by the Great Depression, naval service in World War II, world travel, books, endless curiosity, and family.
Dorothy was born on October 30, 1922, in Worcester, Massachusetts, the first of three children of Frank and Charlotte (Robertson) Raymond.  Her mother died when she was eight, leaving her father, with the help of many relatives, to raise Dorothy and her two brothers, Robert and Richard, during the Depression when jobs were insecure, with occasional weekend visits to cousins in Chatham and summers working at the old Rose Acres Inn in Chatham, owned by an aunt.  In 1939, after losing their house in Worcester, they moved to Auburn.
After graduating from Auburn High School, Dorothy worked at State Mutual Life Assurance Company in Worcester until, in September 1943, she enlisted in the Navy WAVES (Women Accepted for Voluntary Emergency Service).  Dorothy initially hoped to become an aircraft mechanic, as a way to support Bob, a B-17 bomber pilot, but the Navy did not then allow women in that role.  Not wanting the office-worker positions typically given to WAVES, she instead joined with a small group of women sent to aerial gunnery school in Pensacola, Florida.  Dorothy then taught gunnery to naval flight crews in San Diego and Hawaii, reaching the rank of specialist (G) first class. When her father died in 1946, after the war ended, Dorothy left the Navy, returning to Auburn to take on the role of guardian for her brother Richard, then still a teenager.  
In September 1946, Dorothy enrolled in the College of Business Administration at Boston University, graduating with a bachelor of science in business administration degree in June 1950 (receiving honors for three years), while commuting from Auburn, taking care of Dick, and working afternoons and evenings in the MIT development office, and she continued to take evening courses at the Metropolitan College until 1953.  Following graduation, finding that opportunities for women, even with business degrees, were limited, she joined Trans World Airlines as a ticket agent in its new Boston office, later also working at TWA ticket offices in New York and Philadelphia, until she retired in 1985.  
Her position at TWA entitled her to fly standby anywhere in the world.  And she took full advantage, often going to the airport with only a red TWA carry-on bag to take the first flight she could board, travelling, by herself, to, among other countries, Afghanistan, twice, Bhutan, Egypt, the Soviet Union, and throughout Europe, and flying regularly to England to visit relatives, see London shows, or just pick up the London Times.  Dot frequently surprised friends and family by turning up unexpectedly at their vacation destinations around the world, and she brought back stories of her adventures to her enthralled nieces and nephews.
For most of her career, Dorothy lived on Beacon Hill, attending, and keeping the playbills from, virtually every production at the Huntington Theatre.  In 1985, she moved to the North End, where she served as the treasurer of the Friends of the North End Branch of the Boston Public Library, a docent with the Friends of the Boston Harbor Islands, and a volunteer gardener at the Old North Church.  In 1966, Dorothy bought the house on Indian Hill Road in Chatham owned by her cousin Tom and his wife Janet, when they built a new house next door, down the road from her brother Bob and his wife Jean ,across from Janet’s cousin, Dick McKey and his wife Marie, and beside Rudy and Lee Junda, and she moved permanently to Chatham in 2016.    
In Chatham, Dorothy attended almost every lecture and program at the Historical Society and the Council on Aging, joined a wood turners group, equipping her basement with lathes and other wood carving tools, taught herself chair-caning and other skills, and filled her house, and her attic and garage, with books on almost every subject.  More importantly, she continued her role as aunt and honorary aunt to the children and grandchildren of Bob and Jean, Tom and Janet, Dick and Marie, Rudy and Lee, and other cousins and friends.  Even at age 100, she could recall the names of the leading actors and actresses in the movies she attended in the 1930s, and the name of the friends she attended them with, she read the Boston Globe daily, cutting out articles of interest to share, and she continued to tell detailed stories, many stories, of her travels and her family.  
Dorothy will be interred at the Massachusetts National Cemetery in Bourne on October 6.  Family and friends may gather to remember and celebrate this remarkable woman at the Bob and Jean Raymond house on Indian Hill Road North at 2:00 p.m. on October 7.  Dorothy would appreciate donations in her memory to the Friends of the Chatham Council on Aging and the Chatham Historical Society.
For online condolences, please visit www.nickersonfunerals.com.