Herbert (“Herb”) Francis Geiling (September 4, 1949 - February 28, 2026) of Ashfield, MA, suddenly and peacefully passed on from this world at the age of 76 surrounded by his family. 

Herb was born in New York City, raised in Teaneck, NJ, and attended Xavier High School in Manhattan, a Jesuit Catholic school for boys. From his earliest days, he possessed a sharp and irreverent sense of humor and was a natural-born prankster. Alongside his oldest sister Linda, Herb was known for his spirited antics, including a childhood prank of sailing old vinyl records like frisbees into neighbors’ yards.

After graduating from University of Connecticut with a B.A. in English, Herb moved to Randolph, Vermont where he taught 6th grade. His journey led him to Conway, MA, where he met the love of his life, Jean. They married in 1983 and settled in Ashfield to raise their three children: Luke, Ethan, and Caroline. More than anything, Herb was a most wonderful husband and father who filled the home with music, games, books, and a never-ending sense of fun. His devotion to Jean and his children was the foundation of his life, and his legacy lives on in the curiosity, open minds, and confident spirits he instilled in them.

Beloved by the Ashfield community where he lived for 42 years, Herb built a life surrounded by neighbors who became as close as family. He and Jean raised their children alongside a tight-knit group of friends, embodying the true spirit of the phrase "it takes a village." These deep-rooted bonds were the heart of his life in the hilltowns, creating a network of support and friendship that spanned decades.

Herb had an entrepreneurial career path. He opened a bicycle shop in Vermont, followed by another one in Conway (Pine Cycle Bicycles) with his brother Chris where they sold bikes and led tours. After a stint selling computers for HP, he launched his own business (Will Run Computers) in the 1990s during the early days of personal computing. He traveled throughout Western Mass to support organizations and individuals setting up and managing new technology.

Herb was a true searcher, possessed by a lifelong fascination with history, literature, and poetry. His curiosity brought him great joy. His spiritual journey was equally vast, leading him to explore a wide variety of religious, health, wellness and meditative practices. He was quick-witted, audacious, and loved to debate and discuss topics with family, friends, and strangers.

One of Herb’s greatest passions was the world of books. His life was defined by the joy of reading and a genuine curiosity for what others were reading, often greeting friends and strangers alike with a question about their current book. He was a fixture at local book sales, constantly hunting for hidden gems to add to a collection that eventually transformed the family barn into a used bookstore. Herb even turned his love of books into a family adventure, mentoring his children as mini-entrepreneurs by teaching them how to buy and sell titles on eBay in the platform’s earliest days.

A creative soul, Herb was also a dedicated writer who over the years loved to compose everything from short stories and poetry to extensive letters back and forth as the tooth fairy.

Music was a constant companion in Herb’s life. Whether he was listening to the Beatles or picking up the accordion he had played since childhood, he was always looking for ways to share a song with those he loved.

Herb was a deeply present father, helping with school projects, building theater sets, and coaching softball. He famously faced a "father’s dilemma" during a Pinewood Derby final when both of his sons raced against each other, leaving him to cheer for both sides of the track. Whether on the sidelines or in the classroom, he was a dedicated mentor who instilled a lifelong love of learning and a sense of fun in his children.

Beloved by his children’s friends and his nieces and nephews, Herb was the heart of the fun. He was a fierce but playful competitor at games like Scrabble, Chess, Blokus, and Backgammon. He had a unique gift for sparking imagination, whether he was constructing Star Trek control rooms for battle or dreaming up magical adventures in the house and backyard.

Herb was also extremely competitive about the finer details of life. This was most evident in his annual holiday card rivalry with his sister, Tricia, as the two battled to see who could claim the title of the season's earliest card sender.

He was predeceased by his parents, Herbert Geiling Sr. and Eleanor Geiling, and his brothers, Larry Geiling and Paul Geiling. He is survived by his wife of 42 years, Jean Ferris; his children, Luke Geiling, Ethan Geiling, and Caroline Geiling; his sister Linda Gagne (Joe); his sister Tricia Geiling (late Walt); and his brother Christopher Geiling. He also leaves behind his sister-in-law Barb Geiling; his nieces and nephews, Kaitlyn (Arthur), Jennifer (Jeffrey), Dylan, Sarah, Alethea (David), Colin (Cici), Bryanna, Allison (Mike), Kim (Andrew), Nick, Laura (Matt), Ellen (Matt), Andy (Terry), Tim (Amy); and his many great-nieces and great-nephews and a loving extended family of in-laws.

Donations can be made to Tulgey Wood (www.tulgey.org) the Ashfield Fire Department (EMS), or Highland Ambulance EMS.

A Celebration of Life will be held on May 23, 2026 at 2pm at The Congregational Church in Ashfield, MA, followed by a reception.