Cheryl Cunningham

Cheryl (Gilbert) Cunningham, 68, of Dunnellon, Florida, passed away on January 24, 2026, in Clearwater, Florida, following a very brief illness. She was surrounded by the love of her children as she passed into the arms of her Lord and Savior.

Cheryl was born in Townsend, Vermont, and was a graduate of Brattleboro Union High School, Class of 1975. She was truly one of a kind—loving fiercely and selflessly, always placing the needs of her family and loved ones before her own. Her kindness, warmth, and generous spirit touched everyone who was blessed to know her.

A devoted mother, Cheryl coached her daughters' middle school softball team and rarely missed a hockey game for her son, cheering him on with pride. She was the kind of friend you could always call on in a time of need—someone who showed up without hesitation and without expectation.

A lifelong animal lover, Cheryl had a special place in her heart for her dogs, who were cherished members of her family and will miss her deeply. She raised her children to share her love of animals.

Cheryl was an avid crafter who loved trying her hand at new and challenging projects. Most recently, she had taken up wreath making and delighted in sharing her creations with family and friends. She also had a love for plants that showed through in her gorgeous gardens and a massive number of potted plants that she adored caring for. Her neighbors would often see her outside in any heat, tending the gardens.

She is survived by her three children: Kristen Weaver of Brattleboro, Vermont; Heather Bacon of Putney, Vermont; and Evan Petersen (Reina) of Livermore California. She was a devoted and loving grandmother to Emily Bacon, Trevor Bacon, Elijah Larson of Putney, and Payton Looman of Brattleboro, who brought her endless joy. She is also survived by many nieces and nephews, all of whom she loved dearly.

Cheryl was one of seven children born to Charles and Leona Gilbert, both of whom predeceased her. She was also predeceased by her sister, Sherry Gilbert; her nephew, Kyle Gilbert of Brattleboro; and her son-in-law, Philip Weaver Jr. of Granville, New York.

In the early 2000s, Cheryl moved to Dunnellon, Florida, where she built a warm and supportive community and formed many lasting friendships. She will be deeply missed by her community, as well as by her family.

Her love, strength, and unwavering devotion to family will live on in all who knew her.

At this time, no public services are planned. A private service will be held at a later date.

In lieu of flowers, the family requests that donations be made in Cheryl's memory to the Windham County Humane Society, in honor of her lifelong love of animals.