Scott R. Raymaakers

1962 - 2025

Scott Robert Raymaakers, 63, of Pittsfield, MA, passed away at home on October 4, 2025, just one day after celebrating his 38th wedding anniversary, surrounded by the warmth and love of his family after a courageous battle with cancer.

Born in Worcester, MA, on May 15, 1962, he was the son of Robert and the late Elizabeth "Betty" Condi Raymaakers. A 1980 graduate of Pittsfield High School, he then went on to earned his degree in Computer Science from Quinnipiac University in 1985. On October 3, 1987, Scott married the love of his life, the former Kim Bartolomei, marking the beginning of a beautiful family and partnership.

Scott was an avid adventurer, with a love for skiing that began early and endured throughout his life. A lifelong passholder at Bousquet Ski Area, he proudly competed as a member of the Pittsfield High School and Bousquet ski teams and adult leagues, later returning to coach his children's teams on those same slopes.

Professionally, Scott dedicated 33 years to Berkshire Life/Guardian, where he served as a respected leader in IT. His unwavering work ethic and integrity earned him admiration across the company. His family was his purpose, and he carried that responsibility with deep seriousness and pride. He worked tirelessly to provide for them, often balancing long hours and frequent travel with packed soccer schedules and early ski mornings. Through it all, his presence was intentional, and every moment spent was one that mattered.

Scott was a kid at heart. His search for adventure was insatiable - the most alive man you'd ever meet. An outdoorsman at his core, he could be found out on 50-mile bike rides, cross-country hunting trips, heliskiing in the mountains, or simply sharing good-natured banter on the golf course. Some of his most memorable adventures were the many hiking trips he shared with his wife, Kim - from backpacking through the Grand Canyon to conquering Half Dome and exploring the breathtaking trails of Glacier National Park. It was never about the destination, but the journey, and they experienced the beauty of world together-step by step. Meticulous, capable, and passionate, he filled his calendar with activity and his life with meaning.

Following his retirement, Scott cherished time with his family and grandchildren - the true light of his life. Always lighthearted and often the butt of a friendly joke, he exemplified what it meant to be a loyal friend, devoted father, and loving husband. His character was steady, his laugh infectious, and the way he showed up for others was truly unmatched. He had a genuine and effortless ability to connect with people from all walks of life, putting others at ease with his charm, warmth, and sincerity. His sense of humor was core to his personality-his laugh and presence filled a room. Loyalty was in his bones; once you were in Scott's circle, you were there for life.

Scott faced his battle with esophageal and leptomeningeal disease with bravery and grit. His strength and resilience were a source of inspiration. He became a source of light and connection at the Phelps Cancer Center, and his family extends their deepest gratitude to the extraordinary team there - especially his nurse, Jenn, and his sister-in-law, Billie Jo - for their care and compassion.

Scott's remarkable character, boundless love for adventure, and unwavering devotion to those he loved leave a legacy that will live on not only through memory, but in the way he made people feel. He reminds us that the best life is one that's fully lived - live boldly, love deeply, and always seek that next adventure. His laughter echoes as a resounding reminder to never take life too seriously.

Scott is survived by his beloved wife of 38 years, Kim; their three children, Tara (Dave) Piccolo, Heidi (Joe) Raymaakers Kennedy, and Eric Raymaakers; his father, Robert Raymaakers; and his three sisters, Donna Coskren, Lynne (Mike) McGee, and Kristen (Chris) Andrews. He also leaves behind eight grandchildren: Bryceon Moody, Colton Kennedy, Cooper Kennedy, Aurora Kennedy, Delilah Kennedy, Parker Piccolo, Wes Piccolo, and his namesake, Scott Piccolo.

A Celebration of Life for all who loved and knew him will be held on Monday, October 13th at 12 PM at Balderdash Cellars in Richmond, MA, to honor the incredible man who gave so much to so many.

In lieu of flowers, donations may be made to HospiceCare in the Berkshires, whose support brought comfort and peace during Scott's final days, and may be mailed to Dery Funeral Home, 54 Bradford St., Pittsfield, MA 01201.

He will be profoundly missed, lovingly remembered, and forever celebrated.