Howard “Woody” Woodside passed away at home on May 2, 2026 surrounded by his family. Born August 17, 1947 in Portland, he was a graduate of South Portland High School and an Army Vietnam veteran. Woody returned home to work in construction until he became Port Engineer for Casco Bay Ferry Lines for thirty plus years. Woody was a Past Master Mason of the Presumpscot Masonic Lodge and a member of the Field Allen American Legion Post 148.

Woody was first and foremost a loving and devoted husband. He and his wife Flora (MacDonald) Woodside had 53 happy years together and became parents of two wonderful sons, Ryan and Matthew. Woody devoted his life to his family. He was involved in Boy Scouts with his sons - many years of going camping, hiking, and canoeing (even learning to swim just for the boys). When scouting years finished, he continued hiking with his good friend Brad Rounds. Brad and Woody logged over 240 trips and summited over half of the 4,000 footers in Maine and New Hampshire. He also enjoyed deer and bird hunting with the Moosehead gang where he acted as “tracker” more than “shooter”. He’d say, “my truck only goes north.”

He put his heart into restoring the farm in which Flora’s family has lived since the early 1900’s. He took great pride in keeping the grounds beautiful, upgraded the electrical with his good friend Tom Driscoll, and always replied “yes, dear” to whatever else Flora requested.

When not working on the homestead, Woody liked nothing better than helping a buddy with any project that needed an extra hand. He was a generous and dedicated friend. Few things in life made Woody more happy than doing things for people he loved. Except painting, he really, really hated painting! He’ll be sorely missed by so many who valued his advice, work, and friendship.

As his illness progressed over the last few years, he returned to his love of mystery novels. He would often read a book every day and make weekly trips to the Windham Public Library.

Above all else, Woody was proudest of his sons and the beautiful families they created. He is survived by his son Ryan, his wife Chanda Turner, and granddaughters Ellen and Kathryn (Kate) Woodside; son Matthew, his wife Heather Meader, and grandson Alaistair Woodside; his brother Roy Woodside and his wife Mary Jane; and his sister Jerri (Woodside) Bradbury and her husband Steve. He was pre-deceased by his parents Howard and Madeline Woodside.

Woody was never one for attention and made uncomfortable by shows of appreciation. He requested there be no services. Instead the family asks that you use what would have been that time to go help someone else or consider making a donation in his memory to the Windham Public Library, Attention: Jennifer Wood, 217 Windham Center Road, Windham, ME 04062.