Hippie Playboy

Planning · Sep 28, 2026 – Oct 10, 2026

Nine Nights North

Pasadena to the Oregon coast the slow way — 1,200 miles of Highway 1 in an 18-foot trailer behind a Jeep, alone. Elephant seals at San Simeon, the whole of Big Sur in one long golden day, a ranch above Pescadero, a bluff over the Pacific where you take what you can get, two nights in the Mendocino wind, and the redwoods on the way to a campground my son picked out near Newport. Fires closed Big Sur to sleeping this year, so the plan bent around them. Most of it isn't booked. That's the point.

Right now
Between stops
Next up
Pasadena, CaliforniaSep 28, 2026
Stops
9

The route

  1. Pasadena, California
    Sep 28 – Sep 30, 2026

    Pasadena, California

    United States

    A couple of days with Mom and my brother before the wheels start turning. The trailer sits packed in the driveway getting hotter by the afternoon. Out on the morning of the 30th — the last day of September, which feels like the right day to leave.

  2. San Simeon, California
    Sep 30 – Oct 2, 2026

    San Simeon, California

    United States

    Two nights here, and the second one is the gift — a whole day with nothing required of me. Hearst Castle sitting up on its hill looking faintly absurd. The elephant seal rookery at Piedras Blancas, where a few thousand animals lie around in the sand bellowing at each other like a bad party. Moonstone Beach in the afternoon. Then out to Ragged Point at dusk to look north at the coast I'm about to drive.

  3. Pescadero, California
    Oct 2 – Oct 3, 2026

    Pescadero, California

    United States

    The Big Sur day. Ninety miles of cliff edge at thirty miles an hour, second gear most of the way, the Pacific dropping away on the left and nowhere to pull over when you want to. McWay Falls. Bixby Bridge. The long empty stretches in between that are somehow the best part. Then Carmel, Monterey, Santa Cruz, and up to ranch country above Pescadero as the light goes. Six hours to cover a distance that should take three. Worth every minute of it.

  4. Ocean Cove, Sonoma Coast, California
    Oct 3 – Oct 4, 2026

    Ocean Cove, Sonoma Coast, California

    United States

    The night with no reservation. Everything on this coast was spoken for months ago, so the plan is to show up early on a bluff north of Fort Ross and hope. Out of Pescadero at first light, over the Golden Gate before the weekend thickens, and up the coast with time to spare. There's a backup if it doesn't work. There's always a backup. But I'd rather it worked.

  5. Westport, Mendocino Coast, California
    Oct 4 – Oct 6, 2026

    Westport, Mendocino Coast, California

    United States

    Two nights, and the only ones where work follows me. Which rules out the pretty options — the loveliest spots on this coast sit down in redwood canyons where you can't see the sky, and I need sky. So instead: an open bluff on the edge of the ocean north of Fort Bragg, nothing between me and the horizon in any direction. It will be windy. The trade is worth it.

  6. Trinidad, California
    Oct 6 – Oct 7, 2026

    Trinidad, California

    United States

    The long day — a hundred and ninety miles, most of it up through the Avenue of the Giants, where the road narrows and the light turns green and you stop caring about how far you've come. Roosevelt elk standing around in the meadows like they own the place, which they do. No signal, no sky, nothing to answer. After two days of working, that sounds exactly right.

  7. Brookings, Oregon
    Oct 7 – Oct 8, 2026

    Brookings, Oregon

    United States

    Crossing into Oregon. Old-growth groves on the way up, the kind where the trees were already old when anybody thought to name them. Then out to the coast, where the sea stacks stand offshore like leftovers from a different and rougher coastline. First night in a new state. The light changes here — colder, cleaner, more north in it.

  8. Bandon, Oregon
    Oct 8 – Oct 9, 2026

    Bandon, Oregon

    United States

    North through the Samuel Boardman stretch, which is a hundred pullouts and no time to take them all, then Gold Beach and on to where the Coquille River meets the sea. Last night alone on the road. Face Rock at sunset if the fog holds off, and if it doesn't, the fog is its own thing worth standing out in.

  9. Beverly Beach, Newport, Oregon
    Oct 9 – Oct 10, 2026

    Beverly Beach, Newport, Oregon

    United States

    The one stop I didn't choose. My son picked it and handled it, just north of Newport where a creek runs under the highway and out to the sea. An easy half day up the dunes coast to get here, which is the right way to arrive anywhere — unhurried, with the afternoon still ahead of you. Nine nights, twelve hundred miles, and somebody waiting at the end of it.