Madison Cunningham, 21, of Freeport was in a car with a friend on Sept. 24, driving over the Edison Bridge in Fort Myers, Florida, to a wedding 2 miles away.

Madison Cunningham, 21, of Freeport, died in a car crash in Fort Meyers, Florida, on Sept. 24. Her mother said she was spunky, “full of life.” Lisa Cunningham photo

They never got there.

Some street racers were headed across the bridge in the opposite direction. One of the racing drivers lost control of his car, which jumped the median at an estimated 120 mph and crashed into the vehicle Cunningham was in with her friend Josh Casciano, his 2-year-old niece and his sister, Madison’s mom, Lisa Cunningham of Freeport, said Saturday.

Madison, Casciano’s sister and his niece, as well as the driver of the other car, were killed. Casciano was injured. The crash was so violent that the racing car exploded on impact, Cunningham said.

It was the second tragic loss that Freeport has had to endure in a period of days. Theo Ferrara, 14, was found dead in Maquoit Bay on Tuesday after he was reported missing days earlier and a massive search was launched.

Ferrara was a student at Freeport High School. Madison Cunningham graduated from Freeport High in 2019 and still lived with her mother.


As authorities were searching for Ferrara on Sept. 24, two Freeport police officers and a chaplain knocked on Cunningham’s door at 10:15 p.m.

“You know when you open the door and there’s police officers, something’s not good,” Cunningham said.

In the days that have followed, Cunningham said she’s “in shock. I can’t believe she’s not coming home.”

Complicating the tragedy for Madison’s mother, Hurricane Ian has since left much of Fort Myers flooded and without power.

“Of course that means because of the hurricane I have not been able to go down and retrieve her,” Cunningham said. The funeral home handling her daughter’s cremation lost power and the phone connection is spotty. She does not know when she’ll be able to go to Fort Myers. On Saturday, she was waiting to hear when the medical examiner’s autopsy report would be finished and her daughter’s body released.

Madison was her oldest of four daughters. She was outgoing, spunky.


“She’s very full of life. She was my wild child,” her mother said.

“She was huge into Halloween,” Cunningham continued. She loved going to costume stores and bonfires, wearing “Chucky” T-shirts, watching scary movies. Fall was her favorite season.

She was very social, rarely home, her mother said. “She had so many friends,” and was always busy with work or bowling, hiking, camping, playing pool.

Madison Cunningham, who worked at the Freeport Dunkin’ for four years “and knew everyone,” died Sept. 24 in a violent crash in Fort Myers, Florida, said her mother, Lisa Cunningham. “She was my wild child.” Lisa Cunningham

Madison loved tattoos. After the U.S. Supreme Court’s decision to overturn federal protections for abortion rights, Madison got a tattoo of a barbed wire uterus to protest the high court’s ruling, her mother said.

Madison worked for four years at the Dunkin’ in Freeport. She was supposed to start a new job Monday.

“Everybody in town knew her,” Cunningham said. She also worked as a preschool teacher at the Toddler Inn in Cumberland, and as a nanny. She loved children, her mother said.


When the crash happened, Madison was sitting in the back seat with Casciano’s 2-year-old niece. “She was in heaven” sitting with the toddler, her mother said.

Besides her mother, Madison leaves three sisters, Justice, 20, Dakotta, 17, a senior at Freeport High, and her youngest sister, Trinity, 15, a sophomore at the high school. She is also survived by Lisa Cunningham’s partner, Jim Richards, and grandparents Bill and Sandy Roepke of Auburn, and Nance Roepke of Madison, Cunningham said.

The Freeport community has responded, Cunningham said. Someone made arrangements for a meal train for the family. Flowers have been sent. “The school’s been great,” she said. “Everybody loved her.”

A celebration of Madison’s life is planned for Oct. 28 at the Cunningham Farm (not a family relation) in New Gloucester, Cunningham said.

But on Saturday, she said, “my biggest concern is getting her home.”

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