FREEPORT – Madison Jane Cunningham, 21, died tragically from a car accident on Sept. 24, 2022, while visiting Fort Myers, Fla. Madison was born in Auburn, Maine on Dec. 1, 2000, and was the first-born daughter to Lisa and Aaron Cunningham.

As a child, Madison and her sisters could always be found playing outside chasing bugs or catching frogs in the mud holes. They formed a great sisterhood bond, that will live on forever. Madison’s childhood friend, Emma Curtis, was always in the mix with camping and fishing in the local water holes. Madison was a Girl Scout from Kindergarten all the way to Freshman year of high school. She enjoyed summers at the family camp and anything outdoors.

Madison attended elementary school at Marica Buker in Richmond, Maine and moved to Freeport in 5th grade. Madison graduated Freeport High School in 2019 with a Certificate of early Childhood Education from Region 10. Madison loved working with children and continued that love working at Toddle Inn of Cumberland. All through High School, Madison proudly served the Town of Freeport their Dunkin Coffee with a big smile and side of Sass!

Madison had a love of adventure, spending time with her friends, and her annual family road trips to her Emme’s, Aunt and Cousins in Madison, Wis.. Her love of travel that was instilled at a young age continued as a young adult with traveling to Puerto Rico in 2020, New York City in 2022 and most recently the family annual trip to the Midwest. It was no surprise when she told us she was off to Florida for the weekend.

Madison also enjoyed true crime and listening to Podcasts. She had a love of all music and enjoyed sitting around a bonfire with friends and family. She could always be seen facetiming her friends near and far. Madison gave her whole heart to her family and friends and had the most contagious laughter.

Madison was predeceased by her grandparents, Marjorie and Gary Poulin of Richmond; and her second mother, Kelly Lewis of Pownal. Madison’s great grandmother, Thelma Radanov of Madison, Wis., passed away this past February at the age of 105. Madison enjoyed many ruthless Rummy 500 games with Nana and recently got a Queen of Hearts Card tattoo in her honor which was one of many tattoos that showed her love for Halloween and the outdoors.

Madison leaves behind her mother, Lisa Cunningham and her partner James Richards of Freeport, and a father, Aaron Cunningham of Chattanooga, Tenn. She will be missed terribly by her three sisters, Justice, Dakotta, and Trinity Cunningham, her stepsister, Ashley Demuth (Ryan) along with nephews, Caleb, Cohen and Bentley and her stepbrother, James Richards and niece, Hazel; grandmother, Nance Jane Roepke of Madison Wis.; aunt Karen Bay (Brandon) of Sun Prairie, Wis.; and cousins Laney and Charlie. Also, grandparents Bill and Sandy Roepke of Auburn; aunt Sara Kidd; and Godmother Michelle Klauke and family of Chicago, Ill. Madison was very fortunate to have a large extended family on James Richards side as well, including four aunts and many cousins. Many best friends, including but not limited to, Tavia, Ashley and Sam and many family friends. And of course, also her beloved dog Kojo.

A Memorial Service will be held on Oct. 28 at 4:00 p.m. at the Cunningham Farm (no relation) at 1007 Intervale Road, New Gloucester, with a Celebration of Life to immediately follow until 9:00 p.m.

All that loved Madison through the years are welcome to come and share stories and celebrate her short but full life.

Fly High Baby Girl!

In lieu of flowers,

Madison would have wanted you to be yourself, enjoy life and roll one