Visitation
Obituary of Sandra J. Riley
Sandra J. Riley, 56, of Pound Ridge, NY, formerly of Winchester, MA, passed peacefully during a courageous battle with breast cancer on November 24, 2025. Sandra was an endlessly loving mother to her sons, Ward and Ross Whitehead of Pound Ridge, NY. She is survived by Sam Whitehead of Pound Ridge, NY and cherished by her devoted parents Richard and Maureen Riley of Winchester, MA, her siblings Hannah Riley Bowles and husband Ian of Dover, MA, Joan Riley Driscoll and husband Craig of Winchester, MA, Maura Riley Haskell and husband Tim of Carlisle, MA, and Dr. Alan F. Riley and wife Carrie of Cape Elizabeth, ME. She is also survived and adored by her nieces and nephews, Margaret and Jack Bowles, David and Daniel Driscoll, Caroline and Sandra Haskell and Anna and Allison Riley. She is deeply loved by her large extended family and was blessed with many close friends.
A graduate of Winchester High School in Massachusetts, Sandra received her Bachelor of Arts degree in English from Barnard College, Columbia University (‘91), where she made lifelong friendships. Sandra went on to receive a Master of Fine Arts degree in Writing from Columbia University and was a published short story fiction writer. Sandra began her career as an editor at Columbia Business School in 1999. She moved on to work as a Communications Specialist at Weill Cornell Medical College of Cornell University and New York-Presbyterian Hospital. In 2003, Sandra joined The College Board as Senior Director of Communications and was subsequently named Vice President of Communications in March 2016. She was personally committed to increasing college access for underserved communities.
Sandra’s greatest joy was her sons. She cherished every moment with her boys, their many ski adventures, explorations in national parks and beach days. She eagerly travelled to support her boys at sporting events, joyfully cheering from countless hockey stands. Every August, Sandra vacationed on Cape Cod, surrounded by her extended family, delighting in watching her boys play in the ocean alongside their close-knit cousins.
Sandra was adored for her endless generosity, deep intellect, fun-loving spirit, and her laugh that filled the room. Sandra is deeply loved and will be profoundly missed by all who were fortunate enough to know her. It is hard to imagine a world without her broad smile.
The family requests that in lieu of flowers, donations be made to Memorial Sloan Kettering Cancer Center
Visiting hours will be held on Monday, December 1st, from 4 to 8 pm at Clark Associates Funeral Home, 4 Woods Bridge Road, Katonah, NY 10536.
