In 1902 the city contracted with the Olmsted Brothers to have a grand plan drawn up for a system of connected parks and boulevards. Automobiles had come to Seattle just two years prior but the Olmsted Brothers were sophisticated in their thinking when compared to some others. Their vision acknowledged that the horse drawn buggy was on its way out and that “pleasure drives” in automobiles were the future for Seattle. The shoreline of Lake Washington was a great place to build yet-to-be-planned parks and to locate such a grand connecting roadway with its pleasing and complex curves. In 1904 they sent partner James Frederick Dawson to Seattle to review plans, document progress and ground truth their planned visions for the city.
In August of 1904 construction began on the first section of roadway before the plans had even been finalized. That road started at the east end of the Madison Street Trestle and descended north along the hillside that was tightly squeezed between the deep and wooded ravine to the west (today referred to as Washington Park Playfield) and previously platted land between what we refer to today as Washington Park Playfield and Broadmoor.