The Hotel Waucoma was built in 1904, one of the first brick buildings erected in Hood River, and its second major hotel. Built by P.F. "Dad" Fouts, Hotel Waucoma originated with 27 guest rooms, several of which could be converted into suites. Magnificent wooden verandas wrapped around the north and east of the second and third floors, where guests could stroll and take in the spectacular views of the Columbia River and Washington bluffs.

A spacious barroom was planned as a highlight of the grand hotel, but was never realized with the onset of prohibition. Fouts battled prohibition, which was likely the reason the Hotel Oregon wasn’t considered as "socially acceptable" as the Mt. Hood Hotel (currently Hood River Hotel). After five years, Fouts sold Hotel Waucoma to Charles Hall and Ernest Smith, who promptly constructed a four-story addition onto the building’s south and west sides, and changed the name to Hotel Oregon. After the addition, guest rooms totaled 100.

In 1911, the wooden verandas were torn down to make room for concrete sidewalks. Over the next decades, ownership of the hotel changed numerous times, enjoying varying levels of success.

In the 1950s, after construction of the Columbia River Highway, hotel business in Hood River declined, and the Hotel Oregon fell into a state of disrepair. It closed in 1972 because of fire code violations.

During the eighties and nineties, the River City Saloon and an occasional restaurant operated on the ground floor while the rest of the building sat vacant and condemned.