Remembering Jessie Ann Cashen, January 6, 1937 - November 2, 2024

Jessie “Ann” Cashen died of natural causes on November 2, 2024, at her home in Lenox, Massachusetts. She was 87 years old.

Ann was a natural connector for her community and her family. She always had a smile for everyone and wanted others to feel included and loved. She strived to fill life with warmth and laughter and make her friends and family feel special and understood. It always felt like she was focused in on you, with laser-beam attention. She was a person with an optimistic outlook, and her enthusiastic energy was contagious.

The second of four children born to Mary and Robert MacLeod, Ann grew up in Washington, D.C. She graduated with honors from Western High School and then traveled by train to Ithaca, NY, to attend Cornell University. She majored in psychology and also enjoyed studying art history, literature and music appreciation. She was a member of the Delta Gamma sorority. During her senior year, she met Tony Cashen, and they married shortly after graduation.

The early years of Ann’s marriage were spent relocating multiple times for Tony’s career and starting a family. Three daughters, Ann, Sally and Linda, arrived in relatively quick succession. By the time the family got to Scarsdale, NY, Ann was ready to settle in and become part of the community. For the next 40-plus years, Ann was happy to call Scarsdale home, becoming involved with community activities and finding a spiritual home at St. James the Less Episcopal Church.

Ann loved helping children learn. She worked as the Nursery School Director at St. James the Less for about 10 years. During this time, she went back to school, receiving her master’s degree in Early Childhood Education from Manhattanville College. After her divorce she courageously forged a new path as a single mother, working for several years at a public relations company in New York City. She also worked as a real estate agent in Scarsdale, helping many new families settle into the area. Later, she pursued advanced studies in information technology. She retired as database manager for Mamiya America, importer of professional photography equipment.

Ann loved being involved with her community. At St. James the Less, she served on the vestry and the Altar Guild, also taking stints as a Sunday School teacher, greeter, and, for many years, rummage sale coordinator. Later she helped others feel at ease as a front desk greeter at Phelps Hospital and an ESL tutor in Tarrytown.

For the last five years of her life, Ann lived at Kimball Farms, a retirement community in Lenox, Massachusetts. She loved living in the Berkshires, with its forested hills and quaint villages and towns. As chair of Kimball Farms’ trips committee, she organized outings to local sights, like the Clark Art Institute in Williamstown and Mount Greylock Reservation, the highest point in Massachusetts. On summer Saturday mornings, you could find her at Tanglewood, listening in on rehearsals of the Boston Symphony Orchestra.

Ann was an influential force for her five grandchildren, sharing her love of reading, history, and travel with them. She took each grandchild on a special Wyoming trip to a destination of their choice when they reached the age of ten. The Alaskan wilderness, the islands and waters of Hawaii, a dude ranch in Colorado, baseball parks of California and Arizona, and a Disney cruise in Florida were all explored in this special way. Her family meant so much to her.

Ann’s family celebrated her life at a private gathering on November 29. A funeral service and interment of ashes will be held at St. James the Less in spring 2025. Donations in her memory can be made to the National Parks Foundation or Tanglewood.