Richard S. Castaldo, 69, of Concord, N.H., passed away peacefully at home on March 12, 2026, after a courageous battle with cancer.

To know Rich was to know he was “living a dream.” Ask how he was doing—whether he was at the driving range, spending time with family, or doing nothing at all—and that was always his answer: delivered with a bright smile and the familiar twinkle in his blue eyes.

Born Nov. 2, 1956, in New Rochelle, N.Y., Rich spent his early years bouncing between the basketball court and the golf course before heading to Bentley College in Waltham, Mass., where he met the love of his life, Susan.

Rich graduated from Bentley in 1978 with degrees in Management and Computer Systems, part of one of the early graduating classes in this emerging field. Rich and Susan married that same year and built a life together centered on family, laughter, and partnership.

They welcomed two daughters, Kate in 1987 and Karolyn in 1992. The family later settled in Bedford, N.H., where they enjoyed watching them grow up and made many cherished friends.

Technology became the foundation of Rich’s long and successful career. After building his own business, Success Systems, he later joined Fidelity Investments, where he spent many years and ultimately retired as Senior Vice President of Technology.

Retirement allowed Rich to focus on the things he loved most: time with family and time on the golf course.

His passion for golf began in his youth as a caddy and stayed with him for the rest of his life, taking him to courses around the world. Even when the game became more difficult for him, he always found a way to enjoy it—and to share it with others, including teaching his grandchildren and watching Karolyn develop her own love for the game in recent years.

Rich was adventurous with food and loved researching new restaurants and recipes to try in the kitchen. A total TV and movie buff, he watched everything from cooking shows to classic movies, and catching football games with Kate was a favorite.

More than anything, Rich valued being a husband, father, and grandfather. Being “Dad” and “Papa” was one of his greatest joys and proudest accomplishments. He supported his children and grandchildren in all they did, cheering them on in school, on the field, and in their careers. Going to Dominik’s football games and Gianna’s soccer games, and seeing Shankaya complete her Medical Assistant program these last few years, brought him so much happiness.

Rich will be remembered for his quick wit and endless punchlines, always ready with a joke that could bring laughter to any room. Even during treatment, he brought that same humor to every situation, determined to get at least one smile or laugh along the way.

He is survived by his loving wife of 47 years, Susan Castaldo; his daughter Kate Castaldo-Rice and her husband Raheem Rice, and his grandchildren Shankaya, Dominik, and Gianna; and his daughter Karolyn Towle and her husband Greg Towle, and his grandpups Remy and Ruger. He is also survived by his mother, Barbara Theysohn; his stepmother, Jacquelyn Castaldo; and his brothers, Bob Castaldo and Todd Castaldo. He was predeceased by his father, John Castaldo, and his sister, Kimberley Stusse.

A memorial service will be held on Sunday, April 26, 2026 from 1PM to 4PM at The Great Hall, Bedford Village Inn, 2 Olde Bedford Way, Bedford, NH 03110. RSVP at castaldo.net In lieu of flowers, please consider donating to the Dana-Farber Cancer Institute. https://danafarber.jimmyfund.org/site/Donation2?df_id=2108&2108.donation=form1&mfc_pref=T

The Roan Family Funeral Home in Pembroke is assisting the family with arrangements. To share a memory or offer condolences please visit www.roanfamilyfuneral.com