Dorothy Mae Winn Cecchinato

NORTH CANAAN — Dorothy Mae Winn Cecchinato, 95, passed comfortably and peacefully on June 13, 2025, at Geer Nursing Home. She was born October 4, 1929, in Torrington, the daughter of Leo David Winn and Ester Gertrude (Hart) Winn. She was the oldest of four children growing up in West Cornwall. She attended grammar school at the Cornwall Consolidated School and finally 7-8th grade at the Salisbury Central School. Dorothy graduated from Housatonic Valley Regional High School in 1947 and was awarded the Bay Path College Award. Following graduation, she married her high school sweetheart Anthony F. Cecchinato, Sr. They settled in North Canaan and were married for a wonderful 59 years.

Dorothy was very active in sports throughout her life playing softball and basketball through high school and continuing softball on the Canaan Girls softball team. She was an active golfer and bowler participating in these sports into her late 70’s. She enjoyed skiing and would frequent the slopes at Catamount with her husband Anthony throughout the winter. Several ski trips to Colorado are also fond memories for her and the family. She always enjoyed watching sports and with her husband attended numerous sporting events that her three granddaughters participated in all through high school and college.

Her first job was working as a secretary at the General Electric Company in Norfolk. She worked there for 8 years from 1947 to 1955. After GE, and after raising her son, she began working in 1965 at the Housatonic Valley Regional High School, Regional District One in Falls Village, as the Clerk to the Board for all of the Region One schools. She logged a total of 36 years of service at HVRHS. In 2018, she was one of the first group of Honorees inducted to the HVRHS Wall of Honor. After retirement, she continued supporting activities at HVRHS through her work with the HVRHS Alumni Committee and the Blue and Gold Alumni bulletin. In addition to her career at HVRHS, she worked on the Planning and Zoning Commission in North Canaan and was also the chairman of Housing Authority of North Canaan. She worked on the Democratic Town Committee and was a long time member of the North Canaan Board of Education until she was 90. She was an active member in the Cranford Club for many years in North Canaan.
Dorothy is predeceased by her brother David Hart Winn of Marcellus, New York.

She is survived by two sisters: Marion Elizabeth Winn Staples of New Smyrna Beach, Florida; and Gertrude Lucille Winn (Kroehle) Hunker of Falls Village.

Her son: Anthony F. Cecchinato Jr. and his wife Elizabeth Cecchinato of Litchfield.

Granddaughters: Andrea Leigh (Cecchinato) Calore and husband Dan Calore of Watertown, Connecticut; Ashley Lyn (Cecchinato) Labonte and husband DJ Labonte of Litchfield; and Abagail Elizabeth (Cecchinato) Palesty and husband Alexander Palesty of Woodbury, Connecticut.

Great Grandchildren: Zachary and William Calore; Addison, Harper and Vance Labonte; and Greyson, Jack and Callan Palesty
There will be a church service at the St. Martin of Tours Church of St. Joseph in North Canaan starting at 10 a.m. on Friday June 20, 2025. The burial will be at the St. Joseph’s Cemetery in North Canaan immediately following the service. There will be a reception for family and friends to celebrate her life at a location to be determined following the burial.

The family asks that in lieu of flowers to consider making a donation to the North Canaan Cranford Club.