Jacqueline Cipolla, a longtime educator and Oyster Bay resident, has been named the new executive director of the Oyster Bay Main Street Association. Cipolla, 34, officially began her tenure on Jan. 2, following a brief part-time period in December. She brings a wealth of experience in education, nonprofit work, and community engagement to her new role.
Cipolla, originally from Melville, earned her undergraduate and master’s degrees from St. John’s University and holds an administrative license from Long Island University. She spent a decade teaching in both charter and public schools in New York City and Long Island before transitioning to nonprofit work. Cipolla and her husband moved to Oyster Bay in 2017, drawn to the village’s charm and vibrant community.
“Oyster Bay really is such a storybook town,” Cipolla said. “When we moved here, we fell in love with the events, the atmosphere, and the sense of community. Now, to be able to contribute to it through this role is incredibly meaningful.”
Cipolla steps into her role at a pivotal time, as Oyster Bay experiences a wave of younger families moving to the area. One of her primary goals is to raise awareness about the OBMSA and increase community involvement.
“Before applying, I didn’t even know the Main Street Association existed,” Cipolla said. “I want to ensure that more people, especially new residents, know about the organization and the positive changes it helps bring to our town.”
Cipolla said her vision includes not only continuing the organization’s current initiatives but also expanding its reach and membership base.
“The more people who get involved, the more support we’ll have to scale up events and projects for the community,” she said.
Two initiatives Cipolla said she is particularly excited about are the Gold Coast Book Fair and the Seedling Program.
The Gold Coast Book Fair, a partnership with Theodore’s Books and former Congressman Steve Israel, is a multi-day event celebrating literature and community. Meanwhile, the Seedling Program engages local youth groups, such as Boy Scouts and Girl Scouts, to beautify the town by planting flowers in community spaces.
“These projects showcase the variety of what we do for the community,” Cipolla said, “from larger-scale events to smaller ones.”
Cipolla expressed eagerness to collaborate with other local organizations, businesses, and government entities. She has already begun meeting key community partners, thanks in part to the OBMSA’s holiday stroll event in December.
“Everyone has been incredibly welcoming,” Cipolla said. “I’m looking forward to building strong working relationships to continue making Oyster Bay a wonderful place to live and visit.”
One of the areas Cipolla is focused on improving is the lack of awareness about the OBMSA among some residents.
“Many people don’t realize the role the Main Street Association plays in the community,” she said. “We need to do a better job of getting our name out there and showing how we contribute to the vitality of Oyster Bay.”
She said she plans to tackle this challenge through outreach, partnerships, and innovative programming to attract more families and young professionals.
Cipolla said her background in education and event planning has prepared her well for her new role. As a teenager, she interned at Henry Schein Inc., organizing large-scale back-to-school events for underprivileged children. That experience ignited her passion for planning and executing projects that make a difference.
“It’s about being the liaison between multiple groups to make something wonderful happen,” she said. “That’s what excites me most about this job — bringing people together to create something meaningful for our town.”
Cipolla’s enthusiasm and dedication are already evident, and she is optimistic about the future of the OBMSA under her leadership.
“This hamlet has given so much to me and my family,” she said. “Now, I have the opportunity to give back, and I couldn’t be more thrilled.”
For more information about the Oyster Bay Main Street Association, visit their website OysterBayMainStreet.org or follow them on social media.