Hugh Edward O'Reilly

Hugh Edward O'Reilly Jr. died peacefully in his sleep on Sunday, January 26th, 2025.
Born on December 1, 1976, he was the son of the late Hugh Edward O'Reilly Sr. and Syliva Roberts O'Reilly, formerly of Kensington, Connecticut.
Hugh was the beloved husband of Caroline (Caley) Cronin O'Reilly, and incredible father to James (11), Reagan (8) and Gunnar (6) O'Reilly, of Rye, New York.
A gentle giant, Hugh was a proud member of the Rye community, who could often be found leading Cub Scout events and coaching his children's sports teams. Ever ready to help anyone in need, Hugh had a big heart and was passionate about celebrating life. Last summer, the Boy Scouts awarded Hugh with the Algonquin District's Commissioner Award of Excellence, which was a strong testament to his leadership and dedication to the community. An alumnus of Loomis Chaffee (1996) and Denver University (2000), Hugh was a collegiate swimmer who went on to become an Ironman, completing the Lake Placid half and full Ironman competitions in 2021 and 2022, respectively.
Hugh was fascinated by the world around him, which sparked a thirst for travel that included trips to Europe, sailing the Red Sea, living on a scuba diving boat in the Galapagos Islands and hiking Machu Picchu. It was his love of adventure that brought him to Hawaii in 2004, where he met his soulmate and future wife, Caley, in Maui. Their first date was at the Pearl Harbor Museum, which was more romantic than it sounds, and they have been inseparable ever since.
Caley was the light of his life and together they were a dynamic team. They had three amazing children, with whom Hugh shared his love of adventure. Whether visiting family and skiing the mountains of New Hampshire, exploring Windsor Castle in England and beaches in Normandy, or sailing on the Long Island Sound at American Yacht Club, he could always be found sharing new experiences with his family and friends.
His last adventure was to a Cub Scout camp out where he was celebrating his son James' Arrow of Light journey to the Boy Scouts. Earlier that day his daughter Reagan scored her first basket in her CYO basketball game, and his son Gunnar had his best basketball game of his young YMCA career. He was beyond proud of all his children and their accomplishments, and his smile and warm embrace will live on in our hearts forever.
He is survived by his immediate family, his mother Sylvia, his brother Biff (Jeanne) and nephews Christopher and Edward O'Reilly, his sister Kelly Considine, his brother Daniel (McKee), his sister-in-law Cammy Cronin Williams (Greg) and nieces Riley, Maddie and Piper Williams and nephew Chase Williams, as well as brother-in-law Teddy Cronin and nephew Henry, and in-laws Bill and Cathy Cronin. He is preceded in death by his father, Hugh, his brother-in-law John Considine, and more recently his aunts Florence Roberts Skantze and Helene Roberts.
The family will be receiving visitors at the Graham Funeral Home in Rye on Thursday, January 30th from 4-7pm. A mass of Christian burial will be held at Church of the Resurrection in Rye on Friday, January 31st at 10am. In lieu of flowers, please consider donating to Sea Scouts via the Sea Base Scholarship Fund through Scouting.org, Friends of Rye Scouting at friendsofryescouting.org or the Junior Sailing Association of Long Island Sound via jsails.org.