ANNA MARIA – Former city commissioner and longtime Anna Maria resident Dale Woodland passed away on June 28 at the age of 76 due to complications caused by dementia.
The family plans to host a memorial service in October but those details are still being worked out.
Dale served eight consecutive two-year terms as an Anna Maria commissioner before leaving office in late 2019. He’s survived by his son, Jason Woodland; daughter-in-law, Meghan Woodland; seven grandchildren; younger sister, Melanie; and former wife, Gayle. Dale and Gayle’s son, Scott, passed away in 2020.
After relocating from Canada at a young age, Dale grew up on Mangrove Avenue in Anna Maria with his parents Maxwell and Marguerite Woodland, sister, Melanie and older brother, Christopher.
Maxwell Woodland served as Anna Maria mayor from 1959-62. According to family members, he suddenly disappeared after completing his tenure as mayor and the family never heard from him again. Dale was about 14 at the time and many years later it was learned that Maxwell died in his home country of Australia in 1963. Christoper Woodland was a U.S. Air Force pilot and died in a plane crash in the 1970s.
After starting their family in east Manatee County, Dale and Gayle bought the property at 134 Hammock Road in Anna Maria in 1986, when Jason and Scott were teenagers, and there they built the house Dale would call home most of the rest of his life.
From 1995 to 2020, Dale and Scott owned and operated Woodland Quality Pool Care.
In his later years, Dale dated Anna Maria resident Jayne Slade-Dashiell for six and a half years.
Jayne, a nurse, first noticed signs of Dale’s dementia in March 2022 immediately after Dale had open heart surgery.
“He never really recovered from that,” she said of the memory issues that gradually worsened. While living in her own home, Jayne cared for Dale as long as she could.
In mid-2024, Dale’s grandson, Michael Stull, moved into Dale’s home and began providing live-in care, assisted by Michael’s girlfriend. They rode out Hurricane Helene at Dale’s home but before Hurricane Milton arrived, the family decided to move Dale to Jason and Meghan’s home in Live Oak.
Dale passed away at The Canopy at Harper Lake assisted living and memory care facility in Lake City.
Commissioner Woodland
Dale’s beloved dog, Lucy, accompanied him to the city commission meetings and often wandered around the commission chambers during meetings.
After Hurricane Irma damaged the City Pier in 2017, Woodland was the only commissioner in support of building a new pier atop the existing wooden pilings, or atop new wooden pilings. Mayor Dan Murphy and the other commissioners opted for a new pier built atop concrete pilings instead. Due to damage caused by Hurricane Milton, another pier replacement project is currently in its early stages.
In 2019, Dale filed his qualifying paperwork with the Manatee County Supervisor of Elections Office seeking a ninth term, but he was disqualified because he paid his $48 qualifying fee with a personal check instead of a check drawn on a designated campaign account. He then sought commission appointment to his vacated seat but the commissioners appointed Joe Muscatello instead.
Dale never sought office again, but when addressing the commission that day he said his path to public service began when he came to a city meeting to complain to the commission and Mayor Ray Simches about Lake La Vista being so shallow and the need to dredge the channel that connects with Tampa Bay.
“That’s how I got involved in the city. Later, Ray asked me if I’d be on the code enforcement board,” Dale told the commission.
Meghan believes Dale’s memory loss contributed to the qualifying fee error.
Family
Meghan shared with The Sun a soliloquy Jason wrote about his father’s passing: “What makes a life? Is it the one with the most toys wins? Maybe it is riches and a luxurious lifestyle. Or could it be Love; giving, receiving and sharing love? For my dad, toys were never his priority. I never heard him want for anything. He had what he wanted and ignored the rest,” Jason wrote.
“Dale took advantage of opportunities that enriched his life. He built a home in paradise and made a dream life he would never leave. If experiences in life, living exactly where and how you want to live count, then my dad was a very rich man.
“Dale loved people and people loved my dad. He once told me that my mother (Gayle) was the greatest woman he ever knew. His grandchildren were the apple of his eye. He opened and shared his home with family, friends and people he knew. My dad never missed an opportunity to make a person happy with a ‘Dale Burger.’
“Dale was born in Canada and became an American citizen. He loved America and the Constitution. And oh, how he loved Anna Maria. So much so that he became your city commissioner so he could be of service.
“And last, but first, my dad loved God. His favorite part of the Bible was the Beatitudes, Matthew 5. These verses were always in his mind on how to be a better person,” Jason wrote.
“I saw his heart break when he lost his dog (Lucy). I saw him support his sons in their endeavors. But what made his life, to me, and what will stay with me, are the stories. My dad was a genius storyteller – and these are real stories, not fables. He had a gift of humbling himself and sharing these stories that would jerk a tear from your eye or have you crying from laughter. He loved it because it made the listener happy. Dale had a fulfilled life and it showed in his stories,” Jason wrote.
“Now my dad is with Our Father, finally satisfied in the Beatitudes and experiencing more love than humanly possible. Dad, I love you and I will see you again one day and I can’t wait to hear the stories you will have to tell,” Jason wrote.
Speaking by phone, Meghan said, “Dale was amazing. He knew so many people and he had so many stories to tell about his life and his parents’ life. Dale was the kind of guy where if you walked by you would be friends. It didn’t matter if he knew you his whole life or he just met you five minutes ago. His house was open for anyone to come visit at any given time. He’d tell people he just met walking down the road to come use his kayaks. He was generous and open.
“He was born in Canada and when he was a young child they moved here. He told me he remembered the day he became a U.S. citizen and it was the greatest day of his life. He was such a patriot. He loved this country and he loved Anna Maria,” Meghan said.
She shared a copy of a three-page feature story that ran in the “Key Look-out” newspaper in August 1959. The newspaper’s coverage area included Longboat Key, Sarasota and Anna Maria Island and their story touted Maxwell Woodland as a “Man of the Keys.” The story recapped Maxwell’s service as a bomber pilot in the Royal Australian Air Force, his career path as an engineer, comptroller and certified public accountant, the life journeys that brought him and his family to Anna Maria and his current status as the Anna Maria mayor.
“He disappeared later and was never heard from,” Meghan said of Maxwell’s mysterious disappearance.
Meghan first noticed signs of Dale’s dementia around the time he started dating Jayne, and as his memory loss progressed he relied more heavily on her.
“He really turned to Jayne for everything. She would answer questions, speak for him and she was like a safety net for him. When Lucy passed away, it was traumatic. He was grieving and he couldn’t be at his house without his dog,” Meghan said.
When Michael took over Dale’s care, the family hoped to keep him at home as long as possible.
“We wanted him to stay in his house until the very last day of his life. That’s where he wanted to be and we didn’t want to take him from the Island. But I found out just how bad Dale was and my son (Michael) said he couldn’t do it anymore,” Meghan said of the decision to bring Dale to Live Oak where she could help care for him.
“He didn’t know where he was. He kept thinking he could walk up the street but he was out in the middle of nowhere,” she said of his time there.
Eventually, the family concluded it was time to place Dale in a memory care facility for his own safety and that’s where he would later pass away.
When sharing the news of this grandfather’s passing on Facebook, Michael wrote: “Some of you may have known my grandpa, Dale Woodland. He was commissioner on the Island for many years and his dad, Maxwell, was mayor many, many years ago.
“It’s come time where my grandpa has gone to be with our Father. He was loved by many people on Anna Maria, and he loved you all and the Island. He was a family man and a man for America. He preached common sense and lived by it too. He spent more time at the Rod & Reel (Pier) than anyone else; and more importantly, knew how to handle a couple too many beers. I’ll forever cherish the times that I spent with my grandpa and I hope that those of you that did spend time with him will cherish them too. Rest in Paradise Grandpa Dale,” Michael wrote.
Friends
Jayne said she and her late husband, Vic, met Dale many years ago when he was campaigning for a city commission seat, and as time passed, they got to know him better.
“My husband passed away eight years ago. I was walking my dog six months later and Dale was cleaning a pool. I asked him about windows, because I was going to get new windows for my house; and he asked me out for a date. He asked me to go to the Island Players with him because he had season tickets. He always bought two season tickets and asked different people to go,” Jayne said.
When asked what she misses most about Dale, she said, “Going on our long walks, whether it be on the beach, down the piers or walking over to Ginny’s and Jane E’s in the morning to see the locals. We also liked to go on long bike rides around the Island, knowing that if we got tired, or the weather got bad, we could get on the trolley. I am an outdoor person and so was he. He loved the mountains in North Carolina and we enjoyed going there to go hiking and see the leaves change. I just loved that he such was an outgoing, friendly person.”
While growing up on Mangrove Avenue, Dale became close friends with fellow Mangrove Avenue resident Bruce Dickins.
Currently a Tampa resident, and soon moving to the greater Sarasota area, Dickins said, “Dale lived down on Mangrove with his parents, on the beach side. I was up the street at a little house called ‘The Mayflower’ and we became good friends. His father was the mayor of Anna Maria and he was very strict. One day, I asked if I could go down there and watch color TV for the first time and I watched my first cartoons in color. Dale was the kind of guy people gravitated too. Nobody disliked him.”
Regarding Dale’s dad, Bruce said, “I don’t know why he left. After being the mayor, one day he was gone. Apparently, he died in Australia.”
Dickins also suffered a childhood tragedy: “My mom died when I was 12, so we moved to Connecticut, but we kept in contact. When I moved to Daytona, I used to go over to Anna Maria to visit. Dale was a great guy and he never forgot me,” Bruce said, noting that he continued to visit Dale and Anna Maria through the years.
From talking to Jayne, Bruce knew Dale’s dementia was getting worse.
“The last time I saw him was last year on the Rod & Reel Pier before the hurricanes blew it out. My wife and I were walking up the pier and we were about 100 feet from Dale and he looked up and said, ‘holy crap.’ We talked for an hour or two. He knew the dementia was setting in and I’d ask him questions and he didn’t know the answers,” Bruce said.
“After we talked, I got a couple pictures of us and told him I was going to leave. We were walking off the pier and Dale followed us and walked with us to the car. I didn’t think that would be the last time I saw him, but I think he knew it would be the last time. He was my oldest friend and I was his oldest friend, I loved him and he loved me back. He was a great guy. I’ll miss him so much,” Bruce said.
Holmes Beach resident and charter captain Scott Moore said, “I’ve known Dale all my life. He was a true islander. He loved to scuba dive. He used to dive underneath the piers to see how many fish were there. Him and Andy Torgeson used to dive a lot together. He was always interested in protecting the environment, the fisheries and the animals here on the Island.
“Dale was a very good commissioner. You could talk to him and he was very sensible, and a gentleman. His favorite spot was the Rod & Reel Pier. He would ride his bike up there almost every day and have a couple beers. He loved that place. We lost the Rod & Reel last year and now we lost Dale. He was a really good man,” Moore said.
Reading aloud some thoughts he wrote down, former Rod & Reel Pier General Manager Dave Cochran said, “Dale was a very unique individual and an interesting person. He loved going to the Rod & Reel Pier and talking to everyone about Anna Maria and its charm. Dale was especially enthusiastic with visitors and children about the local history and activities.
Dale dedicated himself for the betterment of Anna Maria and its people. He always promoted the beauty and flavor of the Island. Having a conversation with Dale was always interesting and enjoyable. Dale was a real character at promoting good feelings and happiness around him. He will be missed and remembered by all.” Cochran said.
Public officials
The Anna Maria City Hall flag was flown at half-staff in Dale’s honor.
“I briefly served with Dale on the commission,” Anna Maria Mayor Mark Short said. “Dale was a well-known figure here in the city and gave years of service to the city as a commissioner and as an involved citizen. On behalf of the city, we were sorry to hear about Dale’s passing and our condolences go out to his family.”
Former Anna Maria Commissioner Doug Copeland said, “Dale loved Anna Maria and spent a good portion of his life trying to make it a better place to live.”
Former Anna Maria Commissioner Brian Seymour said, “Dale was one of the first locals I met when I moved here 16 years ago. I also had the privilege of serving on the city commission with him for three years. There was nothing more important to Dale than his family, his dog and serving this community. I will miss running into him at city events and around the ‘north end’ when we would catch up on how each other was doing. Another true islander lost too soon.”
Holmes Beach Commissioner Carol Whitmore said, “I have known Dale since the 1970s. He was a true islander and a free spirit. He was always smiling and he always had a story to tell. He will be missed.”
