Jean Romano and Mary Henwood, close friends who began their careers together as Rye school gym teachers, closed out their careers together as well when they retired last month.
Romano, 61, a lifelong Rye resident who graduated from Rye High School in 1981, plans to embrace “the freedom of unstructured days.”
“The goal is to take this fitness watch off and have no more schedules or bells and to enjoy the rest of my life,” she said.
Henwood, also 61, started working in Rye in 1986, around the same time as Romano, also is planning to start a new chapter. “A knock on my dorm door changed my life,” she recalled. “My mom was on the hall phone and shared the exciting news that the Rye City School District wanted to interview me for a physical education position. I was over the moon.” She was “just trying to find a teaching job and Rye happened to be the district that called and offered.”
After almost four decades, both have coached and taught dozens of students whose own children they coached on various teams and were their students — turning back-to-school nights into reunions for graduates of the ’80s and ’90s.
Michelle Sciascia Triolo, who graduated from Rye High School in 1991 and was coached by the gym teachers, said her children Kirsten and Tyler also played on teams and had classes with Romano and Henwood.
“I’m incredibly thankful to have had two coaches like them,” Triolo said. “Their care and support left a lasting impression, and I will always remember how much they treated us like more than just players. Years later, they showed that same dedication and warmth when they coached my children, proving that their impact goes beyond generations. They will be deeply missed by many.”
“Mrs. Romano was an amazing gym teacher, and I always looked forward to coming to her classes,” said Rye High rising junior Olivia Prata. “Her enthusiasm and the fun activities she had planned made the quarters so much more engaging and memorable.”
Prata, whose mom, Allison, is a teacher at Rye Presbyterian Nursery School, and dad, Ryan, is a lieutenant in the Rye Fire Department, both grew up in Rye, and also were taught by Romano.
Besides working together over the years, the two have become good friends. Henwood was even in Romano’s bridal party. “Sharing this milestone with her has made the transition even more meaningful,” said Romano.
The two ultimately planned their retirement together.
“We actually walked our retirement letters to Dr. Byrne in the spring,” Henwood said. “I loved walking out of his office, with my arm around my dear friend and I said, ‘We did it!’”
They have grown up together as teachers, and have experienced each other’s ups and downs.
“She has been there for me in all aspects of my life,” Romano said. “She is a caring, thoughtful person that approaches life with a great deal of energy.” For Romano, Henwood brings to mind music from the TV show “The Golden Girls.”
“As the theme song goes, thank you for being a friend. Traveled down a road and back again. Your heart is true. You’re a pal and a confidant,” she said.
Henwood said of her friend: “Her dedication, work ethic, willingness to take risks, passion for physical education and her compassion towards her students and colleagues is what makes her a fantastic teacher.” Most importantly, “I love Jeannie’s laughter.”

Romano began her teaching career at Rye Country Day in 1985 when she was 22, after graduating from Springfield College. Four years later, she moved to the Rye City public schools. For eight years she taught second and third graders at Osborn, then moved to physical education. In 2012, she was named Rye Teacher of the Year for her dedication and love for physical education.
“The difference between teaching in the classroom and teaching physical education is that in the classroom you get to mold your 20 students for the entire year, but in phys ed, you mold hundreds of students,” Romano said.
Rye resident Heidi Fortin said Romano holds a special place in her heart. Her son Julian, now 21, has high-functioning autism. When Julian was 18, Romano took him to Sal’s pizza in Mamaroneck with all of the gym teachers.
“She then realized he loved to walk, and she walked across The Mario M. Cuomo Bridge with him,” she said. “It’s going to be a huge loss!”
Throughout her time at the Rye schools, Romano has taken pride in spearheading projects like the popular circus arts program at The Osborn School — where kids learn to juggle, walk on stilts, and spin plates — and “Walking for Fitness,” a walking and wellness unit in the physical education curriculum.
While many remember Romano as a teacher, hundreds also called her “coach.” She coached many girls’ teams, including JV field hockey, JV basketball, JV lacrosse, JV girls’ squash, modified girls’ soccer, ski team, and modified volleyball.
Henwood began her career at Rye High School when she was 24 after graduating from Hofstra University and getting a master’s degree from Lehman College. By the following year she was splitting her time between Osborn, Rye Middle School, and Rye High, teaching two classes at each building.
“I loved the variety and the opportunity to connect with students across different age groups,” Henwood said.
Henwood also has coached girls’ volleyball, basketball, lacrosse, and tennis, coaching basketball for 25 years and lacrosse for 19.
“For 39 years, I coached at least one season every school year for the Garnets, and I truly loved every minute of it,” Henwood said.
Henwood’s small office at Rye Middle School is decorated with Christmas cards and team photos from the last three decades. A meticulous record-keeper, she still has her varsity lacrosse book, including the roster from her first team in 1989.
Romano vows to continue her involvement in the Rye community as a director of the Apawamis JR Sports Camp. “I enjoy my time at camp and I see myself working for a few more years,” she said.
Romano will “miss my two office roommates, Emily Murphy and Theresa Jelalian, who are not only colleagues but two great friends,” she said. “We shared sowmany great memories and lots of laughs.”
Henwood, however, is heading out of state.
“I plan to spend significant time in beautiful Rhode Island,” she said. “I’m eager to give back to the community by volunteering. I might even take a few classes at the University of Rhode Island to keep my mind engaged.” While Henwood is looking forward to a new chapter, she said New York will always be her home and an “essential part of my life.”
“Jeanie Romano and Mary Henwood have both been staples in our school, Rye community, and in the lives of so many fortunate kids,” said Deb Morgan, RHS class of ’91. “They will certainly be missed by those of us who were fortunate enough to have known them and we can only wish them the best in their well-deserved retirement.


