Oak Harbor Main Street Association Changes Leadership, Cites Finances

The Oak Harbor Main Street Association said on December 22 that its board of directors had decided to part ways with Executive Director Cheryl Grehan, who led the nonprofit through the last year. Margaret Livermore will serve as interim executive director while the board begins a search for permanent leadership. The association, formed about a decade ago to support revitalization of Oak Harbor's Historic Downtown, announced the change in a post on its Facebook page that said, "Our board is working together to ensure a smooth transition while we begin the process of identifying new leadership that aligns with our mission and the needs of our community."

Board President Gregg Lanza pointed to funding shortfalls as the primary reason for the change, describing the situation succinctly as "financial issues." He added, "In 2025 we did not meet our financial goals, and with the increase in pay and et cetera, we weren’t gonna be able to pay Cheryl through February." The association runs a business and occupation tax credit program that offers small donors a credit equal to 75 percent of a donor's yearly B&O tax bill, and those contributions are used for outreach, marketing, beautification and organization of Main Street activities. Despite efforts to recruit donors to the tax credit program, Lanza said he was unsure why revenue fell short and observed, "I guess a lot of businesses were strapped this year."

Margaret Livermore is familiar to the organization and the community. She previously stood in as executive director following an earlier resignation and later served full time in the role for four years before stepping down in December 2024. Her interim appointment is intended to provide continuity for volunteers and merchants who rely on Main Street programming.

The board expects impacts to affiliated businesses and volunteers to be minimal in the near term, but acknowledged that a permanent hire could take months. The search could begin when the board meets next, potentially after the first quarter. Lanza emphasized the board's collective expertise as a stabilizing factor, saying, "Our board has over 600 years of business experience, some highly successful people, and I tend to think that between all of us we make the right decisions in order to keep Main Street moving forward."

For downtown merchants the episode highlights how local fundraising and staffing decisions directly affect marketing, events and streetscape projects that drive tourism and foot traffic. A prolonged leadership vacancy or further financial pressure could delay initiatives intended to support small businesses at a time when many are already reporting constrained finances. The association's immediate challenge will be restoring donor confidence and securing recurring revenue so that its programs can continue to funnel support back into Oak Harbor's commercial core.