William "Bill" Webster Simmons

William “Bill” Webster Simmons, 81, passed away peacefully on August 1, 2025, in Boston, near his home in Dennis Port, Massachusetts, with his daughters, Celeste and Joelle, by his side. Bill, as he was affectionately known, was born in Pittsfield, Massachusetts to Guy and Ria Simmons on April 7, 1944. Bill was a Boy Scout and then went on to be an Explorer Scout. During his teen years he was actively involved in restoring his cars, which he loved.

After graduating from St. Joseph’s High in 1962, he attended Boston Technical School upon graduation. Bill went on to spend 36 years of railroad service to the New Haven, Penn Central and Conrail. His fondest memories were traveling from the top of the Berkshires in Pittsfield to the foothills in Danbury, Connecticut. He also traveled along the Housatonic, loving the beautiful New England scenery in places like Lee, Rising, Great Barrington, Canaan, Kent and New Milford. 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 and retired to his dream home in Cape Cod, enjoying life in a home full of antiques and beautiful things he loved to collect. 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 the “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. His retirement was also full of love from a gaggle of grandchildren, running around, making him smile.

Bill is preceded in death by his parents, Guy and Ria Simmons 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 grandchildren, Averie, Isabella, and Addilyn. Bill is survived by his brothers, Robert R. Simmons, James E. Simmons and John L. Simmons. He is also survived by his longtime companion, Christine Cataffa, her daughter, Kim and her children, Zoey, Sidney, and Connor.

A Memorial Service will be held on September 20, 2025, at Sacred Heart Catholic Church, 191 Elm Street, Pittsfield MA at 10:00 a.m. A private burial is to be held by family and close friends.