[7] In the early 1850s, two settlers staked claims where the city now stands—Zakarias Martin Toftezen, a shoemaker from Norway; C.W.

Houses and businesses sprouted up along the shores of Oak Harbor as the pioneers relied entirely on water transportation until the 1900s.

The city grew following the completion of Deception Pass Bridge on July 31, 1935, and Naval Air Station Whidbey Island on September 21, 1942.

A nearby state park with 4,100 acres (17 km2) of forest, campsites, and trails was also developed.

Other ways to travel to Whidbey Island include flying or utilizing a ferry service.

[citation needed] Surveys of shorelines throughout the Puget Sound region have indicated that 58% are "unstable".

Average retreat rates range from one to eight centimeters per year and shores in the Puget Sound area, composed of unconsolidated sediment, erode 10 to 100 times faster than rocky shoreline.

[11] Oak Harbor has a Mediterranean climate (Köppen Csb) characterized by warm, dry summers and cold, though not severe, and damp winters.

Due to the Olympic rain shadow, the region is much drier than most of the Pacific Northwest west of the Cascades.

Oak Harbor has favored Republican candidates in each presidential election in the 21st century, though by less than a percentage point in 2020.