John James “Jack” Donahue, 69, of Pittsfield died peacefully on Monday, September 21, 2020 at his home. He was born in Queens, New York on February 6, 1951 a son of the late John Joseph Donahue and Helen Elizabeth (Ruddock) Donahue. Jack graduated from Archbishop Molloy High School in New York City and attended the University of Massachusetts. He was employed for many years by the United States Postal Service and last served as the Postmaster for the Town of Cummington. Survivors include his three children Michael Donahue, Emily Stockman and her husband Ty, Meagheanne Donahue, and their mother, his former wife, Sandy Totter. Jack also leaves three grandchildren Morgan Star Donahue, Henry Maxwell Stockman and Mace Joseph Donahue, two sisters, Sharon Hancharik (Tom), Helen Mary Tvelia (Dennis) and two brothers Brian and Thomas Donahue (Mary), as well as his best friend since childhood, Michael Dantuano. He will also be remembered by his many beloved nieces, nephews, cousins, friends, and his faithful cat, Dmitri. Jack grew up on Long Island, NY, where his boyhood adventures followed train tracks and shorelines. He was a founding member of the St. Ignatius Loyola Youth Council, forging many lifelong friendships there. Jack was a dreamer with a knack for drawing and a great love of books. He was an exceptional storyteller and his children will always lovingly remember him reading “The Hobbit” to them. Jack explored many hobbies, from beekeeping and timber framing, to sailing on a tall ship off the coast of Maine. He enjoyed a continuous passion for learning. In lieu of flowers, the family encourages enthusiastically reading to children, boundless curiosity, and going on adventures. Ar dheis Dé go raibh a anam. A Celebration of John J. Donahue will take place at a later date. The Flynn & Dagnoli -Bencivenga Funeral Home, 5 Elm St. Pittsfield, MA. are in care of arrangements. To add to the Book of Memories, please visit www.flynndagnolifuneralhomes.com.