George I. Rockwood, Jr. ’56

George I. Rockwood, Jr. ’56 died on September 26, 2025, in Milwaukee, Wisconsin.

(The following was provided by Boston Globe in October 1, 2025:)

George I. Rockwood, Jr. ’56

Long-time Harwichport resident George I. Rockwood, Jr., passed away peacefully, on September 26, in Milwaukee, Wisconsin. Born in Worcester, Massachusetts, to George I. Rockwood and Anna V. Rockwood on January 28, 1934, George attended Andover Academy and Bowdoin College, before pursuing graduate education at Wharton Business School. He subsequently enjoyed a lengthy career with Scudder, Stevens and Clark in Boston. George’s father had been one of the six founding members of the Stone Horse Yacht Club in Harwichport, which engendered in young George a lifelong attachment to the club and sailing, as well as Cape Cod itself. He owned multiple boats in his lifetime, including a beautiful wooden schooner and, later, a wooden sloop designed by Sparkman Stephens. His cruising stops as a member of the Cruising Club of America covered much of the world, and nothing pleased him more than taking family and friends on sailing adventures (note: his eldest son hereby apologizes for sinking his prize dinghy, shredding his best mainsail, and dropping a quantity of Kahlua and milk into the bilge of the O’Day 27, eventually causing a hellacious odor). Similarly, his life racing small one-design sailboats and much larger, ocean-going yachts took him to distant locales, including England for the Admiral’s Cup and Florida for the Southern Ocean Yacht Racing circuit. He also completed multiple Bermuda races. George’s marriage to the former Catherine Brown produced three sons, George, III, William, and Charles. He was predeceased by his sister, Ellen; and his son William. He has seven grandchildren and two great-grandchildren. His quietly wicked sense of humor and unassuming demeanor made him a tremendous friend, and the lucky people who knew him best would agree that George was one of the last true gentlemen. His manner and mannerisms truly came from a different century.

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