In Memory of




Obituary for William Raymond Winslow

William “Billy” Raymond Winslow, 76 of Friendship, went home to be with the Lord and his wife Beverly, on August 21, 2023. Billy was born on June 20, 1947, to Robert W. and Dorothy F. (Sidelinger) Winslow in Rockland, Maine.

Billy grew up in Thomaston and attended local schools, graduating from Georges Valley High School in 1965. Before enlisting in the United States Air Force, Billy married Beverly May Benner on August 27, 1966. He served from 1966 to 1970 as a Sgt. Crew Chief on a KC-135 Tanker in the Vietnam War and was stationed in Little Rock, Arkansas. After being honorably discharged in 1970, Billy went on to college for real estate, taking classes at night so he could work and provide for his family.

Billy worked several different jobs in his life. He was a clam digger, lobsterman, he worked at the Button Factory in Waldoboro, as a supervisor at Crowe Rope in Warren for many years and eventually retired from Fisher Engineering in Rockland. Even after he retired, he still enjoyed lobstering his 5 traps and giving the lobsters to his family to enjoy. Billy took many day trips with a friend to dig clams and would tell his family about the adventure when he returned, always laughing because he dug the most clams. Billy enjoyed going dancing every Saturday night with his wife Beverly and friends to see the Country Wranglers. They would travel from dance hall to dance hall to see them. He also loved hosting cookouts and would put on the biggest fireworks display. Billy cherished his garden and would spend hours in it, being sure to plant the peas by April 1st so they would be ready by the 4th of July. For many years, he grew so many vegetables that he had to give them away. He enjoyed using his John Deere tractor and would often make up projects so he could spend time on it. Billy enjoyed going for rides in his new Chevy Colorado with his dog Sheba and would tell you something new that he’d discovered about his truck almost every time he stopped to visit. Billy and Sheba were inseparable. Anywhere he went, Sheba was by his side. He would “take Sheba out to breakfast” every Sunday morning and sometimes other days as well. Days that they didn’t go to breakfast, he would make her breakfast so they could eat together. Billy loved driving down around the shore daily to check on what boats were out to haul and would always say “Sheba wanted to go for a ride”. He loved spending time with his family and would light up any time one of them stopped to visit. Billy loved listening to the “old style” country music like Merle Haggard, Dwight Yoakam and Creedence Clearwater Revival and would often sing along with the songs.

Billy is predeceased by his wife Beverly of 49 years, his parents, his sisters Virginia “Ginny” Cunningham, Vida Kelley and Cynthia “Cindy” Chase, his brother Bobby Winslow Jr., father in-law Dennis Benner, mother in-law Frances Benner, brother in-laws Charles “Jr” Benner, Arnold Benner, George Barter and Joel Maxcy.

Billy is survived by his daughters Melissa Olson and her husband Johnny of Cushing and Rebecca “Becky” Glidden and her husband Dusty of Cushing , grandchildren Michael Hoffses and his wife Jessica of Cushing, Victoria Cormier and her husband Michael of St. George, Chelsea Ennis and her husband Dan of South Berwick, Nicole Glidden of Harrisonburg, Virginia, Dustin Glidden of Cushing, great grandchildren Greyson and Emmett Cormier of St. George, Nova and Hudson Hoffses of Cushing and Weston Ennis of South Berwick, sister Nancy Grover and her husband Alton of Cushing, sister in-laws Alwilda “Diddy” Maxcy and Dorothy Benner both of Friendship, as well as his best friend and companion, Sheba. He is also survived by several aunts, uncles, nieces, nephews, cousins, and friends.

In lieu of flowers, donations may be made in his memory to Pope Memorial Humane Society, 25 Buttermilk Lane, Thomaston, Maine 04861. A graveside service with military honors will be held on Saturday, September 2, 2023, at 1pm in the Sweetland Cemetery, 2361 Friendship Road, Waldoboro with Mark Holden officiating.

Arrangements are with Hall’s of Waldoboro. To extend online condolences, light a candle for Billy or to share a story or picture, please visit his Book of Memories at