For Anne Fligor, veteran educator and assistant principal of the Edgartown School, Friday was a day of milestones. After 33 years on the Island, the day marked the end of Ms. Fligor’s career at the school and the close of another important journey — her time on Martha’s Vineyard.

“Growing up I moved around so much...I was born in New Mexico and moved to California, to Indiana, to Connecticut, to New Hampshire, to Pennsylvania and then to here,” she said on Friday, standing beside the playground behind the school. “I’ve never lived anywhere this long, but I’ve made so many connections and have felt so grounded here.”

It was teaching — and a friend from college — that first brought Ms. Fligor to the Island, she said with a smile. She moved to the Vineyard on a whim in 1987 to work as a home economics teacher, she said. But after 14 years on the job, in 2002, she was offered the position of assistant principal and has been a pillar in the Edgartown school community ever since.

Like so many educators, the highlight of Ms. Fligor’s time at the school has been the moments she spent with the students — from the one-on-one chats in her office to adventures chaperoning school overnight trips to DC and beyond.

“I feel so honored and lucky to have worked here and to watch these kids grow up,” she said, reflecting on the generations of students she has taught. “It’s walking downtown and seeing someone, it’s having the kids of kids that you’ve taught, it’s just having that feeling of community that continues on and on and on.”

The smaller moments will stay with her too, she said.

“When they mispronounced my name, that was always really funny,” she said with a laugh. “They’d call me Ms. Fligular.”

In retirement, Ms. Fligor plans to relocate to Pennsylvania to be closer to her two grown children. But beyond family, she is most looking forward to exploring one of her other great passions — traveling.

“I’ve been lucky enough to be in every state, except for Alaska,” said Ms. Fligor. “I’m looking forward to just being out and about traveling and discovering things. I want to able to get in the car with my husband and show him sites and places I’ve been.”

Before departing on Friday, Ms. Fligor kept the goodbye celebrations to a minimum. Rather than the customary going away gift, Ms. Fligor has asked community members to donate to a playground fund with the hope of purchasing a swing set for the K-1 playground.

“I asked not to have a big send off,” she said. “I really want to have the focus be giving money, continuing to do what needs to be done here.”

Before leaving, however, Ms. Fligor made sure to thank all the faculty and staff who have made her years at the school so memorable.

“My job was to help them to do their job,” she said. “I am amazed every day at what they do, their commitment to the kids, their energy and time they put into it. People come here because they love kids, and they want to help them grow socially and emotionally and educationally and that’s such a blessing.”

And though Ms. Fligor is eager to embark on her next adventure — she and her husband set off on the 8 a.m. ferry on Saturday morning — she promised to visit soon.

“I will definitely be back.”

And in the meantime, she will certainly be missed.

On Friday, as the school day wound down and a group of students ran around the playground in the background, one student approached Ms. Fligor to thank her for her time at the school.

As he walked away, Ms. Fligor’s face broke into a broad smile. “That’s the stuff I’m gonna miss,” she said. “It doesn’t take much but it’s just those little touches that make you sit down and think. That’s why everyone teaches.”