Thomas Winery Plaza

Clear the expectation first: Thomas Winery Plaza is not an operating winery. It's a retail center. Nobody is pouring anything, and there's no tasting room behind the shops.

What it is, is the ground itself: the site of Thomas Vineyards, where Tiburcio Tapia planted vines in 1839 — California's first commercial winery site, marked as California Historic Landmark No. 490. The plaza keeps the historic plaque, old barrels, and Route 66 signage, all free to walk up to.

The smart way to do it: Klatch Coffee's flagship sits in this plaza. Order the coffee, drink it next to the plaque, and you've done one of the shortest, densest history stops on the city's stretch of Route 66. For the rest of the vineyard-era circuit, the Virginia Dare tower is a short drive east.