FOR MORE THAN 15 YEARS,  Tony and I have started our morning with an espresso macchiato and venti bold at Starbucks. It’s not that we love Starbucks, but it is the only coffee shop that’s open at six a.m., which is when we like to head out for coffee since we are early risers. We spend an hour or so chatting and touching base before we start our day. In Brooklyn, we’d keep our daily coffee date even if it meant hoofing it in a cold rain, streetlights still on. We were—are—like the Pony Express.

Regardless of location, Tony and I have learned that the early morning crowd at Starbucks differs from what follows later. In Ashland, the early morning crowd at Starbucks veers male, the same every day, and includes a collection of older, solo men staring at their laptops, one sitting crossed legged, and young unkempt and “unhoused” (Ashland’s term for homeless) men who have slept in the forests above town and leave their gear and dogs in the adjacent walkway while they gather their wits inside. One day, a spaced-out fella at the table next to Tony and me—the tables are a foot apart—interrupted our conversation and asked, “Do you mind if I stare at you?”

TWO BLOCKS FROM OUR HOUSE,  there is a trail called the White Rabbit that leads into the forest, along a creek, and seriously uphill with views of the valley below. It’s a magical world of thick pines and madrones with bark as crimson as blood. The trail winds through the rugged, sprawling Oredson-Todd Woods for two and a half miles and then meets up with the Alice in Wonderland Trail above downtown Ashland. These are public lands.

Locals say there is no need for a trail map. But it’s a down-the-rabbit-hole affair, with a warren of other trails crossing the White Rabbit: Mad Hatter, Cheshire Cat, Looking Glass, Caterpillar, and more. The Pacific Crest Trail appears and disappears, too. Although it may be hard to get lost, it’s easy to feel lost. Lewis Carroll would approve.