William Webster Simmons

William "Bill" Webster Simmons, 81, passed away peacefully on August 1, 2025, with his daughters, Celeste and Joelle, by his side. Bill was born in Pittsfield, MA to Guy and Ria Simmons on April 7, 1944.

After graduating from St. Joseph's High in 1962, he went on to spend 36 years of railroad service to New Haven, Penn Central and Conrail. At Conrail, he was a hands-on teaching manager, treating everyone fairly. Everyone loved working for Bill, and he left an impression on those he knew.

In 1999, Bill retired from Conrail to his dream home in Cape Cod. He loved history and became quite a purveyor of genealogy, educating his daughters and grandchildren about their pasts, even discovering his lineage included Noah Webster, the famous American lexicographer, as well as the British Royal Family. Bill enjoyed giving everyone a "royal waive" when they left his house on the Cape.

A self-taught woodworker, Bill spent his retirement fixing up his beloved home and walking the beaches of Cape Cod. He loved his neighbors in Dennis Port, where a close community formed among them. He was thankful for their friendship.

Bill is preceded in death by his parents, as well as his sisters Rita, Elizabeth and Sandra. Bill is survived by his two daughters, Celeste Jacklett (Steven), Joelle Cook, and beloved grandchildren Nicholas, Mitchell, Matthew, Megan, Jonathan, Sarah and Christopher, as well as great granddaughters Averie, Isabella and Addilyn.

Bill is survived by his brothers, Robert Simmons, James Simmons (Nancy), and John Simmons (Jane). He is also survived by many nieces and nephews, as well as his companion Christine Cataffa and her family.

A Memorial Service will be held on September 20, 2025 at Sacred Heart Catholic Church, Pittsfield, MA at 10:00 a.m. A private burial is to be held by family and close friends.