Three well-known local artists,  Jeanne Valdez (co-founder of Artworks Gallery in Greenbank), Margaret Livermore (founding member of Penn Cove Gallery and founding board member of the Pacific Northwest Arts School), and Joan Brosnahan (founding member of Penn Cove Gallery) established a showcase for the work of local visual artists. The three quickly recruited some of the island's most talented artists and Garry Oak Gallery was born.

Garry Oak Gallery opened on October 1, 2008 to rave reviews. It is not only a stunning showcase for an outstanding range of media, but a lively addition to the Harborside Shops as downtown Oak Harbor continues to provide more and more of the personal service and local goods island residents desire. Garry Oak Gallery is a not-for-profit co-operative enterprise owned by its members. This structure benefits art lovers by allowing the artists to offer greater value than is possible in a commercial gallery setting.