Wilfred Milan O'Brien, 86, passed away at his home on February 3, 2025, surrounded by his beloved family. Known affectionately to many as Wolfie, Wilfred was born on October 20, 1938, in Calais, Maine, the son of Clarence and Christina (Olsson) O'Brien. His life was a testament to his fortitude, his passion for the road, and his unwavering devotion to his family. Possessing an adventurous heart, Wilfred began his trucking career at the tender age of 15. His first haul was with Millard (Milkweed) Glidden to Nova Scotia, and after that, they took a load of Christmas trees to Georgia. This marked the beginning of a lifetime on the road, a journey he embraced wholeheartedly until his retirement in 2018. His dedication manifested in his successful business, W.M. O'Brien & Son Transport, a testament to his industry and the love for his work. On June 15, 1957, Wilfred found his lifelong partner in Mary Ann Dowling of St. Stephen, N.B. Together, they built their forever home on Steamboat Street in Calais, where they raised their cherished families. Wilfred's legacy lives on through his loving wife, Mary; their children, Susan (Roger) McIver, Ronnie (Cindy) O'Brien, Christina Lynn O'Brien Carpenter, Andrew (Bethany Kindiger) O'Brien, Melissa (Jacob) Huntley, and Scott (Moleigh Walsh) Carpenter; his cherished grandchildren, Corey (Lynn) McIver of Princeton, Christy McIver of Baileyville, ,Danielle (Damon) Lefferts of China Lake, and Matthew (Kelli) O'Brien of Pittston; great-grandchildren, Ryan (Taylor) McIver of Princeton, Shain (Nevaeh) McIver of Princeton, Justin & Cayde Huntley of East Machias, Jack Flanagan, Sophie and Bella Lefferts of China Lake, Landon and Charlotte O'Brien of Pittston; and great-great-grandson, Everett Shain McIver, who affectionately referred to him as "Grampy Goofy". Also surviving him are his special nephew Bobby (Bengi) O'Brien of Calais, brother-in-law Bill Dowling of St. Stephen, NB, and sister-in-law Diania (Joey) Green of Grand Manan, NB; and his loyal fur baby Leo who never left his side. He was predeceased by his parents, Clarence and Christina, and his brothers, Gilbert and Bunny O'Brien. Thank you to the hospice nurses and the special care given him at the Lafayette Family Cancer Institute in Brewer. Visitation will be held 6:00 p.m. to 8:00 p.m. Wednesday, February 5, 2025, at Mays Funeral Home, 26 Church St., Calais, where a Celebration of Life will be held 1 p.m. Thursday. Burial will follow in the Calais Cemetery. Donations in Wilfred's memory may be made to Sarah's House, 346 Main Rd., Holden, ME 04429. Wilfred's life was a grand journey filled with love, laughter, and unforgettable moments. His memory will continue to inspire and bring joy to those who were fortunate enough to have known him. We invite you to share your memories and photos of Wilfred on his memorial page at www.MaysFuneralHome.com.