Harold E. "Hal" Healy

Dr. Harold (Hal) E. Healy, 103, of Redding, longtime resident of Ridgefield and Principal of Ridgefield High School, died peacefully after a brief illness, on Tuesday, January 6, 2026. He was the loving husband of the late Mae C. Healy, to whom he was married for 65 years.

Dr. Healy was born on August 22, 1922 in New Britain, CT; a son of the late Maurice and Hazel (Belden) Healy. Growing up in New Britain, he attended Teachers College of Connecticut (now called Central Connecticut State University). Dr. Healy began his career teaching math and science at a regional high school in the small town of Falls Village, CT. He then taught at Middletown High School and served as assistant principal there prior to becoming principal. During these years, he earned his Master’s degree at Columbia University and a PhD from the University of Connecticut.  

In 1960, Dr. Healy became principal of Ridgefield High School. During his 18 years at Ridgefield High School, he oversaw the expansion of a small school with limited programs develop into a larger suburban school, offering an increasing number of programs. He also oversaw the move of the “old” high school at the East Ridge location to the newly built enlarged high school at the current North Salem Road campus in 1972.  

After his retirement in 1978, for over 20 years, Hal had a very successful second career selling residential real estate in Ridgefield.

A resident of Ridgefield for 53 years, in 2013, Hal and his wife, Mae, gave up their beloved home and moved to Meadow Ridge in Redding, CT, where he resided until his death. Hal was an active member of the Meadow Ridge community where he loved participating in activities and socializing with friends, as well as playing bridge several times a week. He was a member of The Rotary Club of Ridgefield for 65 years. He was a participant of The Ridgefield Men’s Club and was awarded honorary status in 2015. Hal received the first award for Excellence in Education from the Ridgefield Old Timers’ Club.   

Hal’s favorite pastime was spending summers at his home in Harwichport on Cape Cod. He enjoyed fishing, boating, checking his lobster pots, playing cards, and walking the beach; but most of all enjoyed a house full of family.  

Hal is survived by his children: Lauren Healy of Wilmington, MA; Scott Healy and his wife Anne, of Duxbury, MA; and Jane Stafford and her husband Scott, of Wakefield, RI. He is also survived by his grandchildren: Brittany Healy, Ryan Healy and his wife Madelyn, Morgan Stafford, and Tyler Stafford and his wife Kaitlyn. In addition, he is survived by his great granddaughter, Nora Mae Healy. He is also survived by his sister-in-law Norma Healy and many nieces and nephews.

In addition to his wife, Mae, Hal was predeceased by his sister Angeline Holler, brothers Maurice “Snow” Healy, and Robert Healy.

A Memorial Service will take place on Monday, January 19, 2026, at 11:00 AM at the First Congregational Church of Ridgefield, 103 Main Street, Ridgefield, CT. Interment will be private and at the request of the family; there will be no calling hours.

In lieu of flowers, donations in memory of Hal Healy can be made to the Ridgefield Rotary Scholarship Fund for Ridgefield High School (RHS) students - https://ridgefield.rotary7980gives.org/hal-healy, or by check to: Ridgefield Rotary Foundation, PO Box 41, Ridgefield, CT 06877.