Oak Harbor Downtown/Waterfront
Pioneer Way & Bayshore Drive
Oak Harbor, WA 98277
Settlement - Oak Harbor was settled in the early 1850s by CW Sumner from New England, Martin Tafton, a shoemaker from Norway, and Ulrich Freund, a Swiss army officer. Freund retained part of his claim – some of which are still occupied by members of his family and a portion of which has been dedicated on the waterfront as Freund Marsh.
The town was named after the extensive stands of oak trees that covered the lands surrounding the harbor. The oak trees were Garry Oaks (quiercus garryana) – a northwestern oak species that grows from Oregon to southern Canada. Most of the oak stands have been cut down – but remnants remain in the downtown district, on the Post Office site, and adjacent to the NAS Whidbey family housing area. The few remaining trees may be over 500 years old.
The town developed about the waterfront since the water was the only means of transportation with the mainland. Between 1900 and the 1930s, early Mosquito Fleet steamers transported passengers and freight between Oak Harbor and the rest of Puget Sound.
Harborside Shops - the historical downtown district is centered on the blocks fronting Pioneer Way between City Beach Street and Midway Boulevard. The 5-block area retains the original streets and most of the building areas that prevailed during the days of the Mosquito Fleet steamers – though some buildings have been replaced or remodeled into Main Street architectural storefronts during the 1930s and 1950s.
The downtown district is undergoing a major revitalization with the addition of new independent shops providing boutiques, restaurants, gourmet food and wine shops, coffee and dessert cafes, and other specialty destination retail and entertainment outlets. Major mixed use retail, office, and residential projects are under development on the vacant lands located along Pioneer Way and Fidalgo Avenue and are a sign of market interest in the district.
The Harborside Shop Association and the Chamber of Commerce sponsor a number of annual events within the district and between the district and Windjammer Park on the waterfront.