Former Milton Councilman Charlie Fleetwood dies

Flags in Milton are at half-staff in tribute to a man who helped shape what the town is today: former Councilman Charlie Fleetwood.

Fleetwood died at his home May 2 at the age of 74 following years of health struggles. He is survived by his wife of 52 years, Barbara, who said Fleetwood passed away in his sleep. 

“There’s a big hole in my heart,” she said. “He was the rock in my life.”

Funeral arrangements have not been made at this time.

Barbara said she has been overwhelmed by the kind words from people on social media and has tried to respond to all of them. 

“Charlie adopted the Town of Milton and it adopted him,” she said. “It had a huge impact on him, and he loved the Town of Milton.”

Fleetwood’s passing was announced publicly at the town council’s May 2 meeting by Mayor John Collier, who described Fleetwood as a dynamic leader and all-around good guy. 

“He will always be missed. His contributions to this community are far too numerous to list. There are few people in attendance tonight who can’t tell you a good story about Charlie Fleetwood. He touched so many,” Collier said, before holding a moment of silence.

The Fleetwoods met on a blind date while Charlie was working for Sears in Wilmington. They came to Milton in 1979 while Charlie was working as a salesman for Graves Uniforms in Lewes.

“I couldn’t afford to live in Lewes,” he said in a 2018 interview. 

Their first house was a rental on Chestnut Street before buying a home on Atlantic Street, where they lived 11 years. In 1992, the Fleetwoods moved to a home on Bay Avenue, where they have lived ever since. 

Almost from the moment he arrived, Fleetwood began serving the Milton community. He served multiple terms on town council, having first been appointed in 1982 and serving until 1996. After leaving council the first time, he became involved with Friends of the Milton Public Library, the Milton Historical Society and Milton Community Foundation, which helped raise money for the John Milton statue in Mill Park on Mulberry Street. He spent a decade as chairman of Milton Chamber of Commerce, established the Governor’s Walk and Bargains on the Broadkill, and served on the town’s 200th Anniversary Committee. 

Fleetwood loved the history of Milton; in addition to the Governor’s Walk, the anniversary and the John Milton statue, Fleetwood wrote a children’s book called “Tales of the Broadkill: Samson’s Saga,” in which a 400-year-old turtle named Samson relays to Fleetwood the history of Milton from the time of Native Americans through the first European settlers to the Revolutionary War era. 

His most notable contribution may be organizing the annual summer Concerts in the Park, which have become a staple of Milton’s summer season. For that, in October 2020, town council formally renamed the gazebo in Milton Memorial Park the Charlie Fleetwood Gazebo. 

Fleetwood was appointed to his final stint on town council in 2016, to fill the seat of Ted Kanakos, who had been elected mayor. It was during this time that his health troubles started in January 2018, when he experienced a series of falls around his home. At the time, he was diagnosed with spinal stenosis, a condition where the spinal column narrows, pinching the spinal cord and affecting nerves going to the brain.

He had to miss many council meetings in 2018 because of treatment, but he eventually returned with the use of a walker. In 2020, however, his condition worsened, and shortly after the gazebo was dedicated to him, Fleetwood resigned from council. 

He was diagnosed with corticobasal degeneration, a rare brain disease similar to Parkinson’s syndrome. The disease causes areas of the brain to shrink and nerve cells to degenerate over time, confining Fleetwood to a wheelchair. He could not comfortably raise his head for very long, leading to periods where it looked like he could be falling asleep.

“Don’t worry, I’m not bored of you,” he would say in his typical down-home sense of humor. 

The Fleetwoods bought a van and outfitted their home with specialized equipment to help manage Charlie’s condition. Barbara became his primary caregiver. 

Former Councilman Emory West was a longtime friend of Fleetwood who often referred to him as his brother from another mother. When Fleetwood had to step down from organizing the Concerts in the Park, West took over. 

“He was my best friend and mentor who taught me a lot,” West said. “We had many good times together fishing, working together on the 200th anniversary and various committees. I learned a lot from him.” 

West said some of his best memories of Fleetwood are when they would get together with friends and go fishing in the Broadkill. 

“It will not be the same, not being able to talk to him. He was a great giver to this town and will surely be missed. I, as have many, have lost a great friend and Barbara has lost a great husband,” he said.

Town Manager Kristy Rogers said, “Charlie was a town icon who focused on Milton’s history and made sure those who knew him also shared that value. Charlie valued the community being brought together for town events, in which frequently he was there behind the camera to capture the smiles. 

“Charlie had a huge heart for Milton and loved it fully. He always positively looked for how a project could benefit the town and how to bring the project to fruition. I’m glad that he was able to achieve publishing his very own book! When Charlie resigned from council due to his health matters, we knew this day would come to pass, but our hearts were not ready for the call. All that knew Charlie well, knew the town administrative staff were his angels, and now he is ours. Barbara, his family and friends are in our thoughts and prayers.”