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Caleb J. Penniman

Caleb Johnson Penniman of Essex died peacefully in the 100th year of his life on Feb. 12, 2024, after a short battle with cancer. He was surrounded by his children and grandchildren in the hours before his death. Caleb, or “Johnny” as he was known for many years of his life, was born on July 18, 1924, in Montreal, Canada, and raised in Wilmington, Delaware. Immediately after graduating from the Hill School, he enlisted in the U.S. Air Force and was deployed to the South Pacific with the 13th Air Force for the final year of World War II. He flew many missions as the top turret gunner on a B-24 Liberator. His wartime experience was meaningful and foundational in many ways, shaping his life and character and fostering a deep appreciation for all that life had to offer. Returning from overseas, he set about to complete his college education at the University of Virginia, followed by a year working for the government in Nuremberg, Germany.

He finally came home to Wilmington, where he met, fell in love, and soon married his beloved wife of 63 years, Anne “Boo” Winchester, who predeceased him in 2015. After marrying in 1952, Caleb and Boo lived in Lake Forest, Illinois, New York City, and Chappaqua, New York, before settling in Essex in 1977.

Caleb never tired of learning, taking classes into his final year, and sharing his knowledge and insights with so many people. His mind remained sharp as his body declined, constantly reading, attending lectures, and working on crosswords. He had a deep love of art and never lost his wonder and sense of joy standing in front of a great painting. Everyone he touched came away feeling that he took a deep interest in their well-being. His warm smile, gentle sense of humor, and colorful sartorial splendor brightened the day for everyone with whom he came into contact.

But his proudest moments were when surrounded by his family, spanning four generations. Caleb is survived by his three children, Mary and her husband Garrett Moran of Greenwich, George and his wife Anne of Essex; Caleb Jr. and his partner Jeanette of Richmond, Massachusetts; grandchildren: Elizabeth, George (Tatiana), and Caleb Moran; and Jeannette (Max) and Amelia Penniman; and his great-grandchildren, Edwin and Helen.

A memorial service will be held at 11:30 a.m. on April 19, in St. John’s Episcopal Church in Essex. In lieu of flowers, the family requests that donations be made in Caleb’s memory to the Essex Land Trust, PO Box 373, Essex, CT, 06426, or to the Scholarship Foundation at Essex Meadows, 30 Bokum Road, Essex, CT, 06426.