Look out along the waters of Oak Harbor and remember the Southern Coast Salish people who occupied the Oak Harbor area long before Captain George Vancouver stumbled upon and named Whidbey Island. Oak Harbor and neighboring Crescent Harbor, which were once densely forested, each featured large village sites with abundant food sources and easy access for traveling by canoe to other areas for trade, ceremony, and war. Today, many sovereign Native American tribes continue to fish in Oak Harbor, keeping the longstanding tradition and culture alive.

The first Euro-American settlers to North Whidbey were quickly followed by many sea captains, predominantly Irish, who helped to establish present day downtown Oak Harbor. Captain George Morse came to Oak Harbor in 1858, ran many successful businesses, and was one of the first to envision Deception Pass Bridge. Captain Edward Barrington, good friend of Captain Morse, owned 1200 acres of present day Oak Harbor and helped to build the only ship to be constructed in Oak Harbor, the Schooner “Growler.” Businesses in downtown Oak Harbor included a wharf, hotel, blacksmith shop, general merchandise stores, and saloon. Prior to the construction of Deception Pass Bridge in 1935, the water offered the only way to get locally grown produce to other markets and bring outside goods to Oak Harbor.

While it might seem out of place, the windmill in Windjammer Park harkens back to the 18 Dutch families who arrived on North Whidbey in 1894. While the Northern Pacific Railroad owned large tracts of land near Oak Harbor, they were never successful in laying tracks, and in the 1890s, the heavily forested land surrounding Oak Harbor was cleared and advertised to those hoping to pursue agricultural endeavors. The Steamboat Idaho brought 18 Dutch colonists to North Whidbey Island in 1894, and while these families originally settled on the outskirts of Oak Harbor, they have left their cultural mark on the city. Steamboats and ships played an increasingly important role in the development of the history of Oak Harbor, and the Steamboat Whidbey would make a round trip from Oak Harbor to Seattle each day, tying up near downtown Oak Harbor each night. All ships coming into Oak Harbor would be met with crowds of people and the docking was treated as a momentous occasion.

In July of 1941, it was announced that Crescent Harbor would become home to a new naval air station for the re-arming of seaplanes, which were essentially flying boats. After Pearl Harbor, construction of the base happened quickly, and the population of Oak Harbor, which had been less than 400 in 1940, grew rapidly. Even with an eye to the sky and an emphasis on aircraft, water continued to be important to the Navy and Oak Harbor. In addition to providing a home to many squadrons preparing to land on aircraft carriers or conduct anti-submarine warfare operations, Oak Harbor and the Seaplane Base was also home to the USS Salisbury Sound from 1963 to 1967. The ramps of the Oak Harbor Marina were once used to get seaplanes to shore and the original seaplane hangar still exists.