Driving the Skyline Boulevard from San Francisco to (almost) Santa Cruz

Alice’s always seems to appear out of nowhere. Even when you are expecting it, looking forward to the homemade blueberry pie or the redneck Benedict, it’s a shock when the tall trees finally open up to reveal the crossroads where the restaurant sits. It’s a tiny place, a wooden cottage with an A-frame roof, and a cheery welcome deep in the Californian forest.

I’d been swallowed up by those trees for what seemed like an eon, following the breadcrumbs of the narrow two-lane road as it curled through the tall redwoods and vivid green fauna. San Francisco and San Jose aren’t that far away, but they might as well be on another planet. This is old-world, pre-tech California, home to genuine lumberjacks rather than bearded hipsters.

I dig San Francisco and can appreciate the hub of activity that is Silicon Valley, but after two days I’m usually ready to get away from the clanging streets, Google buses and insistent panhandling. And my escape is always along State Route 35, otherwise known as Skyline Boulevard. (Any road with the word “skyline in it? Guaranteed good road.)

If you want to get to points south, whether Monterey, California or, hell, Monterey, Mexico, Skyline is a fabulous start. Even though it begins right in the heart of the city, just south of Golden Gate Park, this is not an obvious route.

It is one of the twistiest: There are straight sections but they don’t last long. So if you don’t have the patience, stomach or the adventurous spirit, you can just rocket down the 101 freeway to Monterey’s Cannery Row in about two hours — and miss everything of interest along the way.

Skyline hugs the ridged spine of the Santa Cruz mountains, cutting a high-altitude course that allows for vistas of the San Francisco Bay, the Pacific, and Silicon Valley. Before it exhausts itself (rather unfortunately) 15 miles short of Santa Cruz, it will take you through a swathe of the peninsula that is often overlooked: the thickly forested land east of the ocean and west of Palo Alto.

You could drive it for its entire length, but I rarely do. There are a number of routes that spiderweb off, many leading to the Pacific, and it’s worth making some of those detours even if you end up backtracking a bit.

So while I started the morning on Skyline, passing the zoo and Mussel Rock park, I soon jumped on Highway 1. After Route 66, this may be the most famous road in the land, but few tourists traverse the section just south of town.

The crowded city fades away quickly and the gorgeous views begin right after. Montara Beach and the surrounding park/preserve are secrets I’m loathe to share here (OK—stellar beach, great walking trails), and Half Moon Bay announces the reason for its name from the road. Light sparkled over the ocean and I put all the windows down, tasting salt in the air.

I’d planned a good portion of my day around eating, and my breakfast was at 3-Zero Cafe, the unlikeliest setting for a delicious greasy spoon you’ll likely find. It’s located at the Half Moon Bay airport — which is really just a landing strip surrounded by chain link fence right off the highway.

The cafe is inside the ugly block terminal. In fact, by all appearances the cafe is the terminal. Its name stands for a runway heading and it is chock-full of aviation memorabilia and model airplanes hanging from the ceiling. Against all odds, the food is fantastic and you’ll likely have to wait for a table.

The crab Benedict went down quite nicely.

I stayed on Highway 1 only until La Honda Road (State Route 84), and then cut hard east to meet back up with Skyline. La Honda is another one of my favorites, a driver’s delight that scrabbles through tight turns bounded by guard rails, slowly but inexorably gaining elevation. Caution here is good, as the curves become especially torturous. My steering wheel jigged left and jittered right as I cornered back and forth. (I’ve had passengers get sick here but I was alone today and driving with, ahem, abandon.)

I’d like to claim I stopped at Sam McDonald Park to work off my first breakfast — I’d planned to — as the paths through the woods are pristine. The entire area is laced with hiking trails, especially along Skyline, and there is something special about the solitude of a redwood forest. But I was deep in the rhythm of the road and already thinking of Alice’s, my stomach growling to match the rumble coming from under the hood. I didn’t stop until I hit the intersection of Skyline and La Honda.

Alice’s Restaurant is a destination if not exactly an end point, and the parking lot is usually filled with eclectic vehicles. There were two new Porsches and a phalanx of Harley-Davidsons and a really beautiful old Jaguar E-Type. A guy sitting on a Ducati motorcycle, lazing in the sun, waved me in magnanimously. I didn’t really need the invitation, buddy, but thanks. I swung into the dirt parking lot and killed the engine.

Historical note: Arlo Guthrie’s classic song was not named after this place, but after an entirely different establishment in Great Barrington, MA. This Alice’s was opened subsequently, and apparently coincidentally, by someone who just happened to be called Alice. There’s a bar inside where you’ll meet a truly random crosscut of humanity, from the dude who dropped off the grid after making millions at a startup to a few who’ve never been on the grid at all. It’s a pretty special mix.

I ordered a coffee and sat on the outside deck, considering. My final destination was Monterey, but I was in no rush. I thought of detouring to Pescadero, a western townlet with an old-timey main street that feels like its hosted its share of gun fights.

Good food there, too. But that would entail cutting back to the coast. No, I’d stay the course and ride out the rest of Skyline until it dead ended into State Route 17. Past Santa Cruz, I’d pick up Highway 1 again. The final miles always put me in a pensive mood as the road wends past massive green fields filled with migrant workers exposed to the sun.

First things first, though. Alice’s redneck Benedict comes on a homemade biscuit sopped in gravy, with a side of smoked apple-wood bacon. I put in my order and prepared to fuel up for the journey ahead.

Photos by Talia Herman. Video by Jason Tongen.