Charles Harold Helliwell, Jr. (“Charlie”), 88, passed away peacefully on April 16, 2026, leaving behind a life defined by devotion to family, service, and community. Born October 29, 1937, in New York City, he was the son of the late Charles Harold Helliwell and Nanette Green Helliwell.
Charlie is survived by his beloved wife of 66 years, Karen Roggenkamp Helliwell, with whom he shared homes in Dover, MA, Cape Cod, and Vero Beach, FL. He is also survived by his sister, Sally Helliwell Harper, and her husband, Jack Harper, of Tyler, Texas.
He was a proud and devoted father to Jennifer Helliwell Stoner and her husband, Dick Stoner, of Sherborn, MA; their son, Keaton Stoner of Cambridge, MA; and their daughter, Micayla Stoner Cissel and her husband, Woody Cissel, of Key Biscayne, FL, and their children, Sawyer and Annabelle Cissel.
He was also the loving father of Holly Helliwell Fabyan and her husband, Mark McHugh, of Manchester-by-the-Sea, MA, and Boston; her son, Wesley Fabyan of Seattle, WA; and her daughter, Alyssa Fabyan Brockbank and her husband, Chris Brockbank, of Virgin Gorda, BVI, and their children, Kolie and Elsie Brockbank.
He was sadly predeceased by his son, Charles Harold Helliwell III (“Trey”), in 2001.
Charlie’s early years included a humble start in a two-room schoolhouse in Randolph, New Jersey, followed by boarding school at Phillips Academy Andover on a work scholarship, where he graduated in 1955 with the Aurelian Honor Society distinction. He next attended Princeton University on a Navy scholarship, earning a B.S. in Civil Engineering in 1959. Just four days after graduating, he married his childhood sweetheart, Karen, and the two began their life together with a cross-country drive to San Diego for his service as a Naval Engineering Officer. He served as a Lieutenant (j.g.) aboard the USS Paul Revere, working as a main propulsion engineer.
After completing his military service, Charlie earned a M.S. degree in Civil Engineering from MIT. He went on to a distinguished career in management consulting before spending over 20 years as Deputy Director of the Center for Construction Research & Engineering at MIT. There, he contributed to international infrastructure projects, including desalination and development work across the Far East.
Charlie and his family made their home in Dover, MA, where he was deeply involved in civic life, serving on the Warrant Committee and as a Selectman, volunteering as an EMT, participating in church leadership, and supporting the Dover Foundation.
A lifelong boater, Charlie’s happiest moments were spent on the water either sailing in Tiger Lily or putting around in Tiger Tender. Beginning in 1965, summers in Harwich Port became a cherished family tradition. At Stone Horse Yacht Club, he served in many roles, including Commodore (1983-1984), and was a dedicated mentor to novice sailors. He also enjoyed many years as a member of Dedham Country and Polo Club and later Eastward Ho, where he embraced golf and Cape Cod life in retirement.
Charlie will be remembered for his steady leadership, generous spirit, and enduring love for his family, community, and the sea.
A Celebration of Life will be held on June 28, 2026, at 3:00 p.m., at Saint Christopher’s Church, 625 Main Street, Chatham, MA.