Ann W. Alexander

Ann Walling Alexander, 88, passed away peacefully, surrounded by family, on July 16, 2026, at her home in Dartmouth, Massachusetts. In a life marked by unwavering dedication to others—especially her family, friends, and students—Ann had a remarkable gift for making everyone feel loved and valued. A beacon of kindness, generosity, and grace, she touched countless lives and leaves behind a legacy of warmth, compassion, and joy.

Born in Chicago, Illinois, on December 29, 1937, to Mary Elizabeth Edmonds Walling and William English Walling II, Ann was raised on the North Shore of Lake Michigan in Northfield, Illinois. She was the oldest of three children, followed by her brothers Bill and Wib. She spent her youth playing tennis at Middlefork Tennis Club and forming lifelong friendships through the "Friday Morning Breakfast Club."

After attending New Trier Township High School for two years, Ann enrolled at Chatham Hall, a girls' boarding school in Chatham, Virginia, beginning a lifelong connection to the East Coast. She later attended Bradford Junior College in Haverhill, Massachusetts. While there, she attended a social at Williams College, where she met Charles Christian Alexander. They were married on September 5, 1958, at Winnetka Congregational Church in Winnetka, Illinois.

The newlyweds began their married life in Cambridge and Andover, Massachusetts, before moving to Philadelphia, Pennsylvania. In 1960, they settled at Groton School in Groton, Massachusetts, where they spent the next 48 years raising their family and becoming deeply woven into the life of the school.

At Groton School, Ann and Charlie shared a rich and fulfilling life as teachers, advisors, coaches, mentors, and gracious hosts. For 20 years, Ann served as Associate Director of Admissions, where she was a trusted ambassador for the school, welcoming and encouraging generations of prospective students and families.

Throughout the busy Groton years, Ann embraced every aspect of faculty life. She hosted student parlor game nights, interviewed prospective students, coached girls' tennis, taught Human Relations and Sexuality, entertained trustees and parents, and sang in the choir—first alongside her daughter and, years later, with her granddaughter, Liza. Her home was always open, with an extra place at the table for students, colleagues, friends, and family.

One of her greatest adventures came during the family's first sabbatical, when she enthusiastically embraced a year in Rome with four young children ranging in age from six months to eight years old—even though none of them spoke Italian. She approached the experience with characteristic optimism, curiosity, and good humor, creating memories her family would cherish forever.

Ann also played an important role during Groton School's transition to coeducation in the mid-1970s. From 1978 to 1981, she served as a Dean of the Summer School at Harvard College. Beyond Groton, she volunteered with Trinity College's Parents Fund and later served on the Executive Committee of the Nonquitt Proprietors.

After retiring from Groton School in 2008, Ann and Charlie moved full-time to Nonquitt in South Dartmouth, Massachusetts, where they had owned a beloved summer home since 1997. They embraced the close-knit, family-centered community and quickly became active members of it. Ann delighted in playing tennis, taking full-moon swims with her grandchildren, and preparing meals for family and friends, where there was always room for one more around the table. In her quieter years, she became an avid birder, an enthusiastic reader, and a devoted member of St. Aidan's Chapel. Throughout her life, one constant remained: her love of ice cream.

After surviving COVID-19 following a 45-day hospitalization in 2021, Ann returned home, where she received loving home health care for the next five years. Her family is forever grateful to Laureen Spencer for the extraordinary care, friendship, and devotion she gave Ann, and for the unique bond they shared. They also extend heartfelt thanks to the many caregivers who supported Ann during those years, especially Donna McKane.

Ann was beautiful both inside and out. She was a devoted wife, mother, grandmother, great-grandmother, mother-in-law, sister, aunt, and friend. She showed those around her how to live with kindness, grace, generosity, and love. One of the greatest joys of her final weeks was welcoming her first great-grandchild, Louisa Carroll, into the world.

Ann was predeceased by her beloved husband of 66 years, Charles Christian Alexander; her cherished daughter, Elizabeth Walling Alexander; and her brother, Willoughby George Walling.

She is survived by her three children: Sarah Alexander MacEachern (John), Charles Christian Alexander Jr. (Harriet), and Katherine Alexander Sears (Nathaniel); her nine grandchildren, Liza (Matt), Will, John, Rebecca, Annie, Meg, Charlie, Clay, and Cora; her great-granddaughter, Louisa Carroll; her brother, William English Walling III (Kathy); her sister-in-law, Susan L. Walling; and many beloved nieces, nephews, extended family members, and dear friends.

A memorial service will be held at St. Aidan's Chapel in Dartmouth, Massachusetts, on Friday, August 14, at 11:00 a.m., followed by an ice cream reception at the Nonquitt Casino—a fitting celebration of Ann's joyful spirit and lifelong love of bringing people together.

Memorial donations may be made in Ann's honor to:

· Groton School Charles and Ann Alexander Chair Fund

· St. Aidan's Chapel