Supporting scouting in Rye, NY and throughout the Greater Hudson Valley.
Hugh Edward O’Reilly Jr. Memorial Scholarships
In January 2025, Rye scouting unexpectedly lost one of its most enthusiastic and dedicated parents and adult leaders: Hugh O’Reilly.
Thanks to the tremendous generosity of Hugh’s family and countless friends, Friends of Rye Scouting has endowed a scholarship fund which provides financial aid to any Rye scouts and their families for whom the cost of scouting would be a barrier to their participation.
Each year, a small number of Cub Scouts of Rye Pack 2 and Boy Scouts of Rye Troop 2 typically request and receive some form of financial assistance. If you would like your s to be considered for a scholarship, please contact the current Cubmaster of Rye Pack 2 or Scoutmaster of Rye Troop 2. All inquires will be kept confidential and our approval process is typically based only on “scout’s honor”.
We hope to continue to grow the endowment of the Fund over time — to ensure its perpetuity, provide more extensive support for needy scouts (e.g., summer camp) and perhaps even begin to offer scholarships to other nearby communities and their scouting units (e.g., Port Chester).
As such, we would warmly welcome additional, tax deductible gifts, in the memory of the generous spirit of Hugh — a “scout gone home” too soon.
Donor Roll
(as of March 29, 2025)
We and the recipients of our scholarships are grateful for the tremendous generosity of these family and friends of Hugh and/or scouting:
Anonymous, Cristen Abecasis, Raegan Apostolatos, Jeremy Barr, Scott Beechert, Lisa Benoit, Tim Bittel, Dana Blanton, Anna Bortnick, Robert Briganti, Christopher Carballo, Stephen Carey, John & Kathleen Casey Charitable Fund, Laureen Cassoli, Neil Cavuto, Lauren Chetel, Denise Collins, Michael Connolly, Debra Connors, Mack Cunningham, John Dering, William Ernest, Claudia Fiducia, Paul Fontana, Daniel Fry, Alexander Gleason, Diane Greco, Susan Gurgitano, Matthew Hart, Maureen Hoban, Vilena Katanova, Bonnie Klugman, Angel La Vine, Margaux Lisiak, Timothy Martin, Anthony McGill, Dennis McGill, Diane McGinn, Mary Moran, Chance Moreland, Lauren Morrissey, Brandon O'Daniell, Rory O'Halloran, Meghan O'Reilly, Charles O'Halloran, Kevin O'Reilly, Sally Park, Patricia Shannon, John Spadaro, Meghan Stark, Angela Tammaro, Paul Tramontozzi, Hope Vaughn, Robert Volpe, Phil Williams
If you would prefer to have your name listed in some different manner or removed from this list entirely simply email us and we’d be happy to do so.
About Hugh
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 most worthwhile thing is to try to put happiness in the lives of others.”
— Lord Robert Baden-Powell,
founder of the global scouting movement
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