In our June issue, we explored a John Steinbeck-inspired inland journey from L.A. to Monterey. This month we hit the coast with Jack Kerouac on the road from San Francisco to the Monterey Motorsports Reunion.

Seeing as how Kerouac was a pretty casual guy with his beatnik poetry and free association, we are going to avoid the usual U.S. Highway 101 route. Driving your classic car on Hwy 1 to Monterey can’t be beat. The only question is how soon in your travel itinerary do you want to reach it. To this end we have provided three routes for getting there. Each will take you over country roads and alongside the California seashore, just in different ways. Allow about half a day for each, which will give you time to stop along the way and experience a slower pace of life.

Worth a visit before departing S.F. is Jack Kerouac Alley in Chinatown. Adjacent to this landmark is the City Lights Bookstore, a cultural icon where you can pick up a copy of Kerouac’s classic beat generation book On the Road. From Columbus Avenue you can reach Interstate 280 southbound via Fremont or 4th Street. I-280 will take you to the starting point for each of our three road trips via California Hwy 1.

Road Trip #1: For the most direct route and more time on the coast, take I-280 south to where Hwy 1 splits off toward Pacifica. Following Hwy 1 past idyllic Half Moon Bay all the way to Monterey will provide an enjoyable coastal byway that’s scenic and relaxing. Think of rolling dunes linked by craggy outcrops and unlikely seaside farmlands. This is the route to take when you prefer to just roll down the windows and breathe in the fresh Pacific Ocean breeze. You’ll have plenty of time to stop at a state park or two to dip your toes in the sand.

Road Trip #2: This is the route to take when you are feeling adventurous. Just an hour south of ‘The City by the Bay’ on 280 are roads that will take you through small towns that pass you by in the blink of an eye. Stopping to experience a slice of Americana by engaging in local conversation will provide a journey in the style of Kerouac.

This overland option still allows plenty of coastal views. To start this journey, keep your eyes open on I-280 for Highway 84, also known as La Honda Road. This will take you west over the picturesque hills above Redwood City all the way to the coast. Or you can add a bit more adventure by taking one or more side roads off 84.

One of these side trails begins at Kings Mountain Road in Woodside. This crooked winding switchback hooks up with Tunitas Creek Road and well-known Skyline Boulevard, also known as California State Route 35. Staying on Tunitas Creek will lead all the way to Hwy 1. Following Skyline south takes you to Alice’s Restaurant at the junction of 84. Don’t be surprised if you see a classic car or two parked there.

A second side road begins a bit further along 84 West at the quaint town of La Honda. By taking Alpine Road you can either head south to CSR 35 or cut west on Pescadero Creek Road, a narrow serpentine path through rolling fields dotted by pines and walnut trees. This will take you to the town of Pescadero right next to Hwy 1. As Kerouac once said, “It’s an anywhere road for anybody anyhow.”

In Pescadero you’ll find great food at Duarte’s Tavern. Try their famous seafood, artichoke soup, fish stew, or pie. This family restaurant and bar has been around for generations. Frank Duarte, a Portuguese immigrant, bought the tavern and land for $12 in gold in 1894. You might even spot a local celebrity like Neil Young eating there.

Heading south from Pescadero on Hwy 1 will present even smaller villages like San Gregorio and Davenport. Each has a general store straight out of a scene from Kerouac’s The Dharma Bums. Here’s where you can stock up on picnic goodies for the numerous state beaches on the way to Santa Cruz. Don’t miss photogenic Pigeon Point Lighthouse. Once in Santa Cruz you’ve got about an hour’s drive south to Monterey.

Road Trip #3: Another option, especially if you are starting in Silicon Valley or want to join Hwy 1 later on, is to experience more of Skyline Boulevard. One way to do this is to start at Page Mill Road off I-280 in Palo Alto and head west until it ends at Skyline (CSR 35). Heading south on Skyline will eventually lead you onto CSR 17 that takes you straight into Santa Cruz. A slower paced option is to exit Skyline onto Big Basin Way (CSR 9) toward Boulder Creek and north Santa Cruz.

From Santa Cruz it’s an easy jaunt down Hwy 1 to Monterey. One attraction along the way is noteworthy. For some of the finest “fresh catch seafood” in the Monterey bay area, check out Phil’s Snack Shack in Moss Landing. Delicious!

Once you reach Monterey you can explore even more coastal views along the parkways through adjacent Pacific Grove. Or you can continue onto Carmel’s famous 17-Mile Drive by the sea for a small fee. Further south on Hwy 1 is majestic Big Sur, an easy day trip well worth exploring if you’ve never been.

All of these day trips are quintessential California. Kerouac once wrote, “There is nowhere to go but everywhere.” He was right, of course. And the variety of off-the-beaten-path tours from S.F. to Monterey will allow adventurous travelers to experience that for themselves again and again.

Story and Photos Copyright 2016 Randy Wells. All Rights Reserved.