Punch Magazine - Summer 2026

50 PUNCHMAGAZINE.COM Sharon and banker John Parrot realized that they could enjoy lavish breakfasts overlooking the rolling hills of their countryside estates, take the train to work (perhaps reading the morning paper or conducting a little business onboard), pop into their San Francisco offices for a few hours and be back in the country in time for dinner. A flurry of opulent building projects followed, including James Clair Flood’s “wedding cake” of a mansion with turrets, cupolas and gables in Atherton, Harriett Pullman Carolan’s 98-room French chateau in Hillsborough and countless others. As more and more magnates splurged on country homes, there became a steady demand for lumber from Woodside, bricks from San Jose and imported furniture from San Francisco. Flocks of architects, carpenters and other craftsmen were called in. The economy flourished. COMMUTER COMEBACK There’s nothing quite like a disaster to shake things up. After the 1906 earthquake devastated San Francisco, there was an exodus as many fled the smoldering ruins to start anew elsewhere. “You had cities growing up right around the railroad because the railroad could bring in building materials,” observes Vern. “Most of the cities, still to this day, are centered around the railroad.” Another suburban surge happened in the 1940s and 1950s after World War II. Homes and storefronts began cropping up where farmland once flourished. Meanwhile, more people started swapping carriages for cars. This shift from grass-fed to gas-fed transportation prompted the first paved section of the California State Highway System in 1912, a stretch of road from San Bruno to Burlingame. Accessibility in turn heralded more automobiles. Motor coaches (AKA buses) also gained traction. Suddenly, trains fell out of favor. But as traffic grew more congested and Caltrain officially took over the rail line in the 1990s, our train has made a triumphant comeback. Today, millions of riders, from tech execs to tourists, ride Caltrain annually. For 155 years, this railroad has shaped life on the Peninsula and it shows no signs of hitting the brakes. THE COASTAL LINE The defunct Ocean Shore Railroad—the Peninsula’s lesser-known, coastal line—once lured leisure seekers from San Francisco to the shores of Pacifica, Granada and Half Moon Bay at the turn of the 20th century. Weekend passengers lingered over lunches in open-air cars lined with picnic benches, while farmers relied on the railway to transport the coast’s bounty of Brussels sprouts, artichokes and potatoes. The tracks clung to the coastal cliffs, resulting in breathtaking scenery… and constant problems. The 1906 earthquake sent a devastating 4,000 feet of track plunging into the ocean as the coastal bluffs gave way. After repairs, the fickle terrain and its landslides continued to wreak havoc on the railway, especially at the treacherous stretch known as Devil’s Slide. The route, along with its hopes of someday reaching as far as Santa Cruz, collapsed along with the crumbling cliffs. PHOTOGRAPHY COURTESY OF: SAN FRANCISCO HISTORY CENTER, SAN FRANCISCO PUBLIC LIBRARY

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