Sunnyside played an important role in the development of the first electric streetcar in San Francisco. Before the enterprise was initiated in 1890 by streetcar-railway engineer John Wesley Hartzell, with financial backing from millionaire real-estate speculator Behrend Joost, horse-powered and cable-driven streetcars were the norm. Soon the newly introduced technology would power many of SF’s many privately-held transit lines. But the San Francisco and San Mateo Railway was the first electric railroad in the city.
Central to the enterprise was the Sunnyside Powerhouse, located on the then unbuilt flatiron-shaped block between Monterey, Circular, and Baden.
Although a sparsely populated neighborhood during the decades around the turn of the last century, Sunnyside had both a streetcar—San Francisco’s first electric car—and the Southern Pacific San Francisco-San Jose steam train running along its eastern border. The two lines crossed at an oblique angle, just south of Monterey blvd and Joost Ave—an area now disappeared by the excavations for I-280. It was referred to as the Sunnyside crossing, and was a notorious site of fatalities and injuries during these years.