There are plenty of best-of lists of favorite roadside stops on the L.A.-to-S.F. drive. But in recent years, many NorCal residents are decamping not to SoCal, but to the Pacific Northwest.

The Portland Tribune reports that 40,000 Californians move to Oregon every year, while 20,000 Oregonians move to California. That’s an average of 164 people per day moving their lives between the two states. Many do so by driving the quickest, most convenient route—namely, Interstate 5, or I-5.

I saw this borne out in real life when I moved from San Francisco to Portland last August. The freeway was lousy with moving trucks, trailers, and cars with California plates overflowing with cardboard boxes.

I-5 north of the Bay Area is an underreported stretch of freeway, possibly because it’s a bit more remote, more mysterious than the well-trodden stretch between L.A. and San Francisco, which is basically one giant farm. The drive from San Francisco to Portland is much more interesting.

The road north takes you on quite a ride—through one of the premier olive-growing regions of the world; past crumbling, volcanic Mount Shasta and the red banks of Lake Shasta; and through the valley around Yreka, quirky hippie mountain towns that haven’t changed in decades, and the only town in the country whose economy revolves around live theater—before you finally get to Portland.

Historically, this stretch of land was known as the Siskiyou Trail. Native Americans carved out a series of footpaths, which became increasingly worn when trappers wound through Oregon to California. Now that I am officially a Portlander after a decade in the Bay, it seems like just about every other person I meet came here from California. Our path is well-trodden indeed.

I’ve taken this drive at least seven times now, taking note of the best eats and quirkiest stops along the route from the Bay to Portland.

1. Olive Pit: Corning, California

2156 Solano Street, Corning, California
I-5 exit 631
168 miles north of San Francisco
466 miles south of Portland

The numerous billboards that mark one’s approach to Olive Pit might lead you to believe it’s a tourist trap. It is, but it’s a really excellent one.

Olive Pit has the biggest selection of olive products I have ever encountered, and I spent a month in Italy. The selection ranges from stuffed and brined olives to martini-specific olive juice mixes to some of the most unusual infused olive oils; locally produced offerings are specially marked. I stan the blood orange–infused olive oil as one of the best seasonings I’ve ever used, and I make a point to buy a few bottles every time I pass through.

Olive Pit also has a café and restaurant with American food (sandwiches, burgers) and desserts. The sandwiches are just slightly above average — although there is an olive bar, naturally, to enhance them — but the milkshakes are the real star of this stop. The chefs will mix many olive oil and vinegar infusions into milkshakes. You can get a lemon olive-oil milkshake, a blood orange olive-oil milkshake, or — my favorite — a white balsamic vinegar milkshake. One server told me the blood orange olive-oil milkshake is a bestseller.

2. Evergreen Coffee Shop (and Hotel): Redding, CA

2085 Pine Street, Redding, California
I-5 exit 677
216 miles north of San Francisco
420 miles south of Portland

Evergreen’s look and feel should be familiar to any city slicker. It’s got the Instagram-aesthetic minimalist interior you’d see in any café in any gentrified neighborhood in San Francisco or Portland, and the clientele has that telecommuter-on-a-Macbook look that feels out of place in Redding, which is more of an outdoorsy, religious town. (There are three religious schools in the city, which definitely colors the culture.) The coffee is excellent and the food menu, which has a certain locavore vibe, is great as well.

There’s an attached hotel above, but I haven’t explored that. However, if you’ve ever been to ACE Hotel in L.A. or Portland, it should be familiar.

3. Bogbean Books and Music: Redding, California

1740 California Street, Redding, California
I-5 exit 678
218 miles north of San Francisco
420 miles south of Portland

From left to right: rows of olives and olive products and a tapenade sandwich and balsamic vinegar milkshake. Photos: Keith Spencer

This underrated used media store is like a living archive of 40 years of the format wars. It has books, VHS tapes, records, DVDs, video game systems and games, and old electronic musical instruments. The selection varies, but the shop is full of obscure or hard-to-find media for half the price you would pay in San Francisco. When I was there a few months ago, I found a complete DVD set of Rainer Werner Fassbinder’s acclaimed Berlin Alexanderplatz for just $60, which is a steal for a 15½-hour cult film. Delightfully, the rarities are mixed right in with mass-produced, commercial noughties artifacts—think The Matrix DVDs and Armageddon on VHS.

4.Lake Shasta roadside stop

Turntable Bay Road
I-5 exit 692
229 miles north of San Francisco
405 miles south of Portland

Come on, were you seriously going to drive over that beautiful lake, and those red-banked shores that bleed into the forest, without stopping? Drive slowly down the road, walk to the shore, skip some stones, and skinny-dip; you’re in California, for God’s sake. The lake is very warm much of the year, and it affords some great vistas and photo opportunities.

5. YAKS on the 5: Dunsmuir, California

4917 Dunsmuir Avenue, Dunsmuir, California
I-5 exit 730
267 miles north of San Francisco
366 miles south of Portland

The sidewalk entrance to YAKS on the 5. Photo: Keith Spencer

This may be the most reviewed restaurant between Sacramento, California, and Eugene, Oregon; it has more than 2,500 reviews split between Google Maps and Yelp. It’s a quirky little burger spot with a very sweet staff, and the peculiar decor gives it a bit of extra charm to put it over the top.

6. Any convenience store in Weed, California

I-5 exit 747 toward Central Weed
284 miles north of San Francisco
350 miles south of Portland

I’m convinced Weed’s economy is built on novelty T-shirts with marijuana puns. Aside from the pun-based entrepreneurship, there are a few decent breweries in the area: I make a point to stop at a convenience store and pick up some to-go beers from Mt. Shasta Brewing Company.

And yes, Mt. Shasta Brewing Company is in town and is a great pub, but I cannot in good faith advocate that you stop and get drunk while you’re in the middle of a road trip.

7. The Growler Guys: Ashland, Oregon

345 Lithia Way, Ashland, Oregon
I-5 exit 19
284 miles south of Portland
350 miles north of San Francisco

Ashland is a busy town despite its small size because of its outsize tourist footprint. The Oregon Shakespeare Festival attracts a lot of traffic for much of the year. While there are a number of cafés and restaurants, many of them cater to a crowd that’s more chichi than the average driver just passing through.

I prefer stopping at The Growler Guys when I’m driving through. You get a mini tour of downtown upon approach, which is good for some variation, and the combination café-bar-kombuchery has a lot of drink and food options to choose from, always appreciated on a long drive. A standard-issue second-wave coffee bar greets you at the entrance, replete with snacks, pastries, and energy bars; in the main part of the space, a large tap selection—and a sizable kombucha tap—awaits.

8. The Haul Gastropub: Grants Pass, Oregon

121 SW H Street, Grants Pass, Oregon
I-5 exit 58
391 miles north of San Francisco
244 miles south of Portland

In terms of being both affordable and interesting, The Haul is probably the best restaurant in Grants Pass. It has a diverse but not overwhelmingly big menu, and is fast-casual — you order at the counter — so you don’t feel anxious about leaving immediately at dinner’s conclusion as you might with waitstaff hovering. You can order drinks, coffee, kombucha, or beer on draft if you’re thirsty. The tacos are a standout, and they include unique ingredients (coconut crema?) that elevate them beyond standard roadside fare.

9. Rogue Roasters: Grants Pass, Oregon

610 SW 6th Street, Grants Pass, Oregon
I-5 exit 58
391 miles north of San Francisco
244 miles south of Portland

Rogue is a sort of cultural hub for Grants Pass: It’s a drive-through coffee place, a roastery, and a sizable venue rolled into one. In its spacious interior, you can choose to sit on the patio, in the bustling main room with the register and baristas, or in a quieter side room that adjoins the roasting equipment — it depends on your mood.

Beyond a mere coffee joint, the café, known for its darker roasts, features a number of more peculiar drinks, teas, and kombuchas that make it a worthy stop. And if you crave people-watching, Rogue Roasters will meet your need.

10. The most northerly In-N-Out Burger in the world: Keizer, Oregon

6280 Keizer Station Boulevard, Keizer, Oregon
I-5 exit 260
595 miles north of San Francisco
38 miles south of Portland

Calling this fast-food franchise location the most northerly is a bit dramatic, but technically correct. If you are truly addicted to the simple pleasures of In-N-Out, you may want to jump at the final opportunity to enjoy one. Note that Portland has two excellent local burger chains, Burgerville and SuperDeluxe, that should satiate you upon arrival.