For a good part of its history, getting to Santa Barbara for overland travelers was not all that easy. The city is hemmed in by mountains that meet the Pacific at Gaviota Pass and the Rincon, respectively. In addition, the few passes over the Santa Ynez Range could be difficult, if not downright treacherous. The tremendous growth in the popularity of the automobile in the first decade of the 1900s spurred a movement to construct a decent road in the area around Rincon Point.
Before the completion of the Casitas Pass road in 1878, stagecoaches coming to Santa Barbara from Los Angeles had to take to the beach in the Rincon area. High tides, storms, mud, or rock slides could render this route impassable for even weeks at a time. Although this situation was eased somewhat after the Southern Pacific cut its roadbed into the Rincon hillside as it laid track toward Santa Barbara in 1886, the area remained a dangerous bottleneck.
Even though the troublesome Rincon stretch was in Ventura County, a group from Santa Barbara incorporated in 1910 to construct a private road at a cost of $200,000. The Rincon Toll Company proposed to build a macadam route through the area. Problems over rights of way and the cool reception given the project by the Ventura County supervisors eventually killed the proposal.