Ruth-Ann (Kirby) Flynn, 83

Ruth-Ann (Kirby) Flynn, 83, of Wilton CT ,passed away peacefully, surrounded by loving family, on June 17, 2025, at The Greens at Cannondale.

Born in New Bedford, MA, and raised in nearby Rochester, Ruth-Ann was the daughter of the late George Arthur Kirby II and Ruth Sylvia Hartley. She attended Rochester’s Waterman School and New Bedford High School, and received a B.A. in Government from the University of Massachusetts Amherst, where she was a member of the Pi Beta Phi sorority.

After graduation, Ruth-Ann moved to Washington, D.C., where she was employed by the Republican National Committee. It was there that she met her husband-to-be, Charles P. Flynn (Charlie). The couple would have celebrated their 60th wedding anniversary this August.

From Washington, Ruth-Ann moved to New York City, where she worked as a legal assistant at a Wall Street law firm until her 1965 wedding, at which time she moved to Wilton, CT. It has been her home ever since.

At the time the Flynns moved to Connecticut, the state was experiencing a teacher shortage and had implemented a program offering teaching permits to liberal arts graduates who completed a summer training course. Ruth-Ann jumped at the opportunity, marking the beginning of what would become a 48-year-long career in education. She later earned a Master’s degree in Education from Fairfield University, further deepening her commitment to teaching and learning.

Known to generations of students as "Mrs. Flynn," Ruth-Ann taught both second grade and kindergarten at Ridgebury and Scotland Elementary Schools in Ridgefield. She was active in the Ridgebury and Connecticut Education Associations and participated in contract negotiations for the teachers' union. She was also a member of the Ridgefield Teachers Association, where she was involved at both the state and national levels. Her legacy continues through an annual college scholarship she established for Ridgefield High School students.

Ruth-Ann loved downhill skiing, whitewater and sea kayaking, and, more recently, pickleball. She was a member of the Wilton Garden Club and the Wilton Congregational Church, where she served as an usher and was active on the Mission and Service Committee.

A lifelong dog lover, Ruth-Ann and Charlie shared their home with a series of beloved bloodhounds, and in more recent years, with a basset hound named Maxi.

Though Connecticut was her home, Ruth-Ann maintained lasting ties to friends and family in Massachusetts. She and Charlie traveled north frequently for family gatherings, especially at Christmas and on Memorial Day, to cheer on relatives in Rochester’s annual river boat race. She remained a proud promoter of the family business, the George Kirby Jr. Paint Company in New Bedford. Even in later years, she rarely missed her cherished summer visit to Snows Pond, where she swam, paddled, and sang around the campfire with her nieces and nephews.

Ruth-Ann will be remembered for her kindness, her quick wit, and her sweet spirit.

She is survived by her husband, Charlie; her sister, Meryden Kirby; nephews Mark Hartley, Matthew Hartley, George Kirby IV, and Adam Kirby; nieces Kathy Brady, Shawn Ann Schafler, Dana-Lyn Hartley, and Michelle Kirby; as well as many great-nieces and -nephews, and several great-greats. She was predeceased by her parents and her brother, George A. Kirby III.

A graveside service will be held for Ruth-Ann on Wednesday, July 2, 2025, at 1:00 p.m. at the Sherman Cemetery, Pine Street, Rochester, MA. A reception will follow in the Fellowship Hall of the First Congregational Church, 11 Constitution Way, Rochester. A Celebration of Life will take place at the Wilton Congregational Church on Saturday, July 26, at 2:00 p.m. at Pilgrim Hall.

To offer online condolences, please visit www.boutonfuneralhome.com.