The History: Trains started appearing here in the 1870s, and a community began to form. It soon became clear that the railroad was so important to Santa Rosa, some 50 miles north of San Francisco, that the train depot should be positioned to act as the town square. And that’s exactly what happened. The depot opened in 1904—an impressive basalt structure built by four Italian stonemasons. Wander around to find a wealth of brick buildings full of character—one-story buildings built from 1915–1925 and warehouses from 1888–1914. Besides the depot, though, the one must-see spot—which you can also thank those Italian stonemasons for—is the gorgeous, multihued Hotel La Rose, which opened in 1907.
Where to Play: Stay at the Hotel La Rose—ideally in the historic Main Building on the top floor, where the slanted roof adds character to the rooms. Don’t miss dinner at the hotel’s Bistro 1907; then start the following day with a single-origin cup of joe at Flying Goat Coffee. Theater lovers should check out what’s on at the nearby 6th Street Playhouse. And to get here and away, take advantage of the updated train service, Sonoma-Marin Area Rail Transit (SMART).