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Nicholas Richard Henderson, 45, of Sheffield

The family will hold a private celebration of Nick's life on Saturday, June 22, 2024.

Nicholas Richard Henderson, beloved father, brother, and son, died Friday, June 14, in Sheffield, MA. He was 45 years old.

Nick was born to Peter and Jennifer Henderson on August 12, 1978, in Weymouth, Mass. The family relocated to the Berkshires that same year and eventually settled on Shunpike Road in Sheffield. Nick attended Sheffield Center School and Mt. Everett through eighth grade and graduated from Monument Mountain Regional High School in 1996.

Nicholas Richard Henderson.

From an early age, Nick loved the outdoors, and he spent hours building forts, biking down the dirt roads of Sheffield with his younger sisters, and swimming in the Green River and Umpachene Falls. An avid outdoorsman, Nick loved hunting and fishing throughout the Berkshires with his father and, later, with his own son.

Nick also had a deep passion for football. He played Southern Berkshire Youth Football throughout childhood, and in high school he played all four years for the Monument Mountain Spartans. He played on both sides of the ball, as a defensive end and an offensive lineman, and was named a team captain in his senior year.

Nick’s deepest love was for his two children: Jaimie Leighann Henderson, 24, and Nicholas Peter Henderson, 19. They were, without question, the pride and joy of their father’s life. Nick always called Jaimie his “hero” and proudly watched her obtain a master’s degree in 2022 and embark on her career in the environmental field. And he enjoyed nothing more than supporting his son Nicholas Peter on the gridiron, both as a coach for Southern Berkshire Youth Football and, a few years later, under the lights on Friday nights as Nicholas carved out his own stellar career as a Spartan. Both Jaimie and Nicholas offered their father unconditional love and support; he looked forward to every moment spent in their company and surrounded himself with pictures of their smiling faces.

Nick had a tireless work ethic and an entrepreneurial spirit. In 2001, he founded Henderson Roofing Company with just a dump truck, a few tools, and two employees. The crew quickly drew praise for their quality workmanship and soon entered the newly emerging metal-roofing market. Behind Nick’s vision, craftsmanship, and business acumen, Henderson Roofing became the premier fabricator and installer of standing-seam metal roofing in the Berkshires, and Nick thrived as a sought-after craftsman specializing in complex, creative roofing installations, including architectural copper work. Nick’s custom metal roofs have appeared in architectural magazines, and his work will live on in the Berkshires for decades to come.

Nick was preceded in death by his mother Jennifer Henderson. He is survived by his two children, Jaimie Leighann Henderson of Erie, Penn., and Nicholas Peter Henderson of Lee; his father Peter Irving Henderson of Sheffield; and his two sisters, Holly Henderson-Fisher of Sheffield and Christa Joy Andersen of Easthampton, Mass.

Nick had a kind, gentle heart and an infectious laugh. He lived each day looking forward to family connections, be it his daily phone calls with his father Peter, or his children, attending holiday gatherings and shared meals at his sister Holly’s home, or watching his singer-songwriter sister Christa Joy perform her music live. Nick was deeply loved by his children, his father, and his sisters, and he will be profoundly missed by them all.

The family will hold a private celebration of Nick’s life on Saturday, June 22, 2024.

In lieu of flowers, donations in Nick’s memory can be made to Southern Berkshire Youth Football Scholarship Fund by Venmo to @GOSBYFCHARGERS or email to


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Karen A. Beckwith, 77, of Great Barrington

A graveside service will take place at St. Bridget's Cemetery in Housatonic on Monday, July 29, 2024, at 12 p.m.

Pauline Marie Montgomery, 86, of Housatonic

Cremation has taken place, and the family will announce a burial at a later date. Pauline will be interred in Greenlawn Cemetery along with her poodle, Molly.

Rodney H. Christman, 79, of Sheffield

In keeping with Rodney’s wishes, all services are private.

The Edge Is Free To Read.

But Not To Produce.