As the Oak Harbor Main Street Association replaces its calendars for the new year, Margaret Livermore is passing the executive director’s hat to Cheryl Grehan.

After four years of leading the nonprofit, Livermore is ready to spend her retirement days painting and visiting her grandchildren in Texas. Grehan, who has been serving as the events and logistics manager for the Oak Harbor Chamber of Commerce since the summer of 2023, looks forward to continuing to make downtown a place residents can be proud of.

During the past four years, the association has said goodbye to some businesses and welcomed new creative ventures, turned an unused gravel lot into a pop-up plaza where anyone can enjoy local food and live music in the summer, decorated light poles with colorful banners, constructed and embellished the Serendipity Lane shortcut connecting Pioneer Way to the waterfront and more, in collaboration with the City of Oak Harbor, artists, volunteers and other community partners.

In 2015, Livermore and other community members came together to create the Oak Harbor Main Street Association with the goal of making the city’s historic downtown a place where locals and tourists could shop, dine and have fun. Since then, Livermore said, the area has become more vibrant, offering a range of diverse businesses, photo-worthy views and family-friendly events, like the Sasquatch Walk. In addition to the variety of mom and pop businesses, most of the retail spaces in town are filled, which she said is a good sign.

Livermore served on the board of the association until she was asked to temporarily cover the executive director seat following the resignation of Hayley Samford. Eventually, she transitioned into a permanent position.

While retiring feels bittersweet, she said, she’ll still be around, serving on the association’s promotion committee and welcoming art enthusiasts to the Garry Oak Gallery, which she started in 2008 with Jeanne Valdez and Joan Brosnahan.

After spending her last day greeting visitors in her office and getting emotional over coffee, Livermore can finally focus on painting watercolor sceneries, something she hasn’t done in years.

Art is a passion she has been cultivating since her college years in Oregon, where she studied to become a medical technologist before working at WhidbeyHealth Medical Center.

Livermore was born in Salt Lake City but grew up in the Sacramento area. Since she moved to Whidbey with her husband in 1982, she has been involved with a variety of organizations and initiatives pertaining to the arts, like the Pacific Northwest Art School, the Oak Harbor Music Festival and the Penn Cove Gallery.

Looking back at her years in the Main Street Association, one of her favorite memories was the return of the Santa Parade, which brought joy to people after a long period of social distancing.

Livermore gets emotional talking about the friends made while working as the executive director and the enthusiasm shown by business owners, volunteers and community partners.

“It’s not a one-man deal,” she said. “It’s this whole community that makes this work.”

Marketing Coordinator Teresa Besaw described Livermore as the most hardworking person she’s ever known. While they live in the same neighborhood, she will miss her regular presence in the office.

Grehan, who was born in Louisiana, has been calling Oak Harbor her home since she moved to the city in 1996.

She served in the Navy for nine years, tracking submarines from land at NAS Whidbey Island. Tired of working in an office, she quit her job at Edward Jones in search of a job that could better connect her with the community.

In 2023, the Oak Harbor Chamber of Commerce chose her to plan and coordinate events, like the yearly Holland Happening. Now, that role was assigned to Emily Scolari.

Working for the chamber gave her the knowledge and experience she needed to fill Livermore’s shoes, a dream she’s had for some time, perhaps made more appealing by the Hallmark movie vibe of Pioneer Way.

Grehan will begin working on Jan. 2. In the meantime, she continues to pursue a master’s degree in business administration with an emphasis on project management.

Her goal, she said, is to be an asset to businesses by providing them with advice and guidance.

(Photo provided) Cheryl Grehan, a Navy veteran and the former events and logistics manager at the Oak Harbor Chamber of Commerce, is the Main Street Association’s new executive director.