Capt. Dennis R. Webb ’72

Capt. Dennis R. Webb, 67, of Fellows Street, South Portland, Maine, died peacefully on Sunday, January 21, 2018, at the Gosnell Memorial Hospice House following a long illness. His loving wife was by his side.

Dennis was born in Portland, Maine on May 24, 1950, the son of Rufus H. and Gertrude M. (Butler) Webb. He attended local schools and graduated from Deering High School in the class of 1968 and from Maine Maritime Academy in the class of 1972.

On October 28, 1972, Dennis married the love of his life Caryn L. Sellers in South Portland. They began their married years in Portland where they started a family. They then moved their young family to South Portland. There they raised their daughters and watched all five of their grandchildren play and grow.

Dennis worked his entire career as a Merchant Marine officer, retiring as Captain. He sailed ships all over the world for companies including Texaco, Sealift, and Maersk. Captain Webb was the first captain to sail a cargo ship in to Poland after World War II. He started on oil tankers, but spent most of his career bringing cargo such as grain to countless exotic ports all around the world including Africa and the Middle East and took numerous trips through the Panama Canal. He was a man that saw so much of the world. Captain Webb retired in 2008, after piloting ships all over the world for more than thirty five years.

In his spare time Dennis loved riding his Harley Davidson and was a member of the Mid Maine Hog Chapter. He enjoyed computers and creating computer generated graphics. Dennis was an avid car fan, following NASCAR, local car races, watching auto shows and car auctions on t.v, and researching vintage autos. He really enjoyed owning a truck and loved to customize it. While raising his family, he loved spending time at the family camp on Sebago Lake, waterskiing, and taking the boat out for the day. He enjoyed mudding and ice racing on his 4-wheeler. Dennis was always extremely proud of his running career and even ran in the Boston Marathon. He was a member of the Portland Lodge of Elks and the Maine Maritime Academy Alumni Association. He loved to tour lighthouses- always keeping the sea close to him even when he was ashore. Outside of spending time on the water, his greatest enjoyment came from the time spent surrounded by his family, especially his children and grandchildren, all of whom he adored. Dennis was a strong, loyal, extremely smart, an avid learner, brave, steadfast, kindhearted, adventurous, proud and loving person. He loved to strike up a conversation with anyone who would listen.

His wife and daughters are so very proud of him and his daughters are so thankful for the father they were given. His five grandchildren brought out a beautiful gentleness in him that was heartwarming to witness. He will be extremely missed and will always be in the hearts of his friends and family….forever their captain.

Dennis was predeceased by his father Rufus H. Webb. He is survived by his mother, Gertrude M. Webb of Portland; his loving wife, of more than forty five years, Caryn Webb of South Portland; two daughters, Jennifer and her husband Sean Dial of Saco, and Jessica and her husband Jeffrey Guay of Windham; a brother, Brian and his wife Linda Webb of CA; five grandchildren, Caleb Dyer, Isabelle Dial, Gavin Guay, Isaac Guay, and Dawson Guay; two nieces.

An hour of visitation will be held on Friday, January 26, 2018, from 3:00pm to 4:00pm at the Conroy-Tully Walker South Portland Chapel, 1024 Broadway, South Portland. A Memorial Service will follow at the chapel at 4:00pm with the Rev. Philip Shearman officiating. Burial and a celebration of life will be held in the spring. To view Dennis’s memorial page, or to share an online condolence, please visit