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When I was a kid, most of our vacations were camping trips stitched together by the many National Parks dotting the western states. This Labor Day, I returned to those roots with a San Francisco to Portland road trip.

There are so many route options to choose from for a road trip from San Francisco to Portland, but we anchored ours to Crater Lake, the sole national park in Oregon. It’s a place I’d always wanted to go but had only ever seen from a plane (it’s so big, you can see it from space!).

As with any road trip, ours was filled with hilarious instances, unfortunate mishaps, and gorgeous views.

This San Francisco to Portland road trip itinerary is for 6 days, but I’ve included notes on places we would’ve liked to visit or spend more time at. And of course, you can always reverse this itinerary and use it for a Portland to San Francisco road trip instead.

Let’s hit the road.

Day 1: SF to Mount Shasta

Okay, so technically this itinerary is for 6.25 days. And by that I mean, you need to either get out of the city of San Francisco the evening before or get up super early and get out of the city before traffic hits.

We chose to leave the evening before and got to our campsite outside of Corning, CA around 10 p.m. We were the only folks camping at that olive grove that day, which meant our late arrival fortunately didn’t disrupt anyone’s sleep. (Not familiar with camping on private grounds? Check out Hipcamp and get $10 off your first campsite booking.)

On your first full day, drive up to Mount Shasta for your first taste of the Cascades. It’s a little over four hours away from San Francisco and was just under two hours from our campsite in Corning.

Since we had a little bit of a late start and didn’t get to Shasta until lunchtime, we chose to hike up Grey Butte Trail.

This 3-mile out-and-back trail is easy for active hikers and moderate for the average person. It starts out at the Panther Meadows Campground before winding through a conifer forest and then up for prime views of Mt. Shasta as well as panoramics of the entire area.

If we’d had at least 2 days in Shasta, we might have attempted to summit via Avalanche Gulch Route.

Not sure if the Grey Butte Trail or an overnight hike is for you? This guide provides a pretty good overview of easy, moderate, and hard hikes in the Mount Shasta region for you to choose from.

Word of caution for the Mt. Shasta region — hailstorms can occur at any point, so bring some rain gear and be aware of weather forecasts and how the skies look.

Then drive through Klamath Falls, which disappointingly has no waterfalls despite its name. It does have a pretty solid brewery though, so pop your head into the Klamath Basin Brewing Company.

And finally, find your resting spot for the night at the Sunset Campground at Lake of the Woods.

I cannot say enough good things about this campground inside the Fremont-Winema National Forest. It’s got large campsites with campfire rings, potable water, clean bathrooms, and on-site hosts (employees of the Lake of the Woods resort, the concessionaire for this federal campground).

And it’s right next to this gorgeous lake.

If we had more time, we definitely would’ve stayed another night there and either went out on the lake or done some hiking nearby. Waking up to this light through the trees is worth it in itself.

Day 2: Crater Lake National Park

The drive from Lake of the Woods to Crater Lake is roughly 90 minutes. Here, you’ll need to pay an entrance fee of $25 per car or buy an America the Beautiful annual pass for $80.

I was so happy to finally see Crater Lake in person.

It is so blue, so clear, so big. In many ways, it reminded me of Lake Tahoe in the summer as well as Heavenly Lake, the crater lake that bridges China and North Korea on the other side of the world.

As with many national parks in the U.S., you don’t need to be physically fit to see the glorious nature that has been granted this country. But if you want a more active visit, there are dozens of hiking trails around the lake as well as elsewhere in the park.

We started with the Garfield Peak Trail, a steep but relatively short hike that grants you these amazing views of Crater Lake. We saw little kids and elderly folks going up this trail, so take your time, and you can make it, too!

Looking to hang up our hammock and chill, we decided to keep it to one hike a day and proceeded to drive to our campground. And that was the start of the biggest mishap of the trip.

Well, let’s just say someone booked us a similarly named campsite in Utah instead of inside Crater Lake National Park.

With it being a holiday weekend, all of the first-come, first-serve campsites were very much taken up. We also didn’t have a backcountry camping permit in hand and weren’t going to make it to the permit office before it closed for the day.

Fortunately, after some initial “ahhh, maybe we can just sleep in the car” moments, we were able to find a nearby sno-park that doubles as a free campground in the summers.

We were able to hang up the hammock and find some wood for a fire, but then came the rain. I suppose reading in the tent instead of the hammock had to do.

Day 3: Crater Lake & Bend

In the a.m., we packed up our gear and headed back into the park.

One of the fascinating things about Crater Lake is that it is purely filled by rain and melted snow. Yet despite having boat tours and allowing people to get into the water, the water is crystal clear.

So. Damn. Clear.

The only proper way to get down to the lake is via the Cleetwood Cove Trail, a steep decline that leads you straight to the water.

If you dare to jump or wade in, just be prepared for breathtaking chill. Even when the weather is in the 80s outside, the water remains bone-chilling — it rarely reaches beyond 55° Fahrenheit even on the hottest of days.

Basking in the sun after you get out of the water? Now that’s what lake days are for.

When you’re ready to say goodbye to this gorgeous beauty, hit the road for a two-hour drive to Bend.

I know there’s way more to Bend than craft beer, but you can’t fault me for associating that with this central Oregon city.

Since we were headed to Portland in part to visit friends, we unfortunately weren’t going to be able to give Bend the time it deserves. So we were singularly focused on one thing: beer.

First stop: Crux Fermentation Project.

This brewery warehouse plus giant backyard is the stuff of summertime beer dreams. You can try their many brews while munching on something from either their extensive in-house menu or from one of the food trucks in the yard. Bonus points: the place is dog and family-friendly.

Then it was off to the original Deschutes Brewery & Public House for a bigger dinner and drinks. If I wasn’t so tired, we likely would have hit up a few other spots downtown as well. But alas, I was ready to pass out.

Instead of spending the night in a hotel, we chose to camp at this bison and yak ranch a few miles out of town. And it was perfect.

The skies were so clear — great for stargazing — and the ranch was super cute (you can rent the teepees if you want). Plus, it was where we finally got to shower on this San Francisco to Portland road trip.

Day 4: En route to Portland

This itinerary isn’t really fair to Bend, I know. We’ll have to go back one day and give it more dedicated time. Besides the breweries, we really only got to see some art in Tin Pan Alley.

Of all the Bend things we missed out on this trip, the one thing I’m so upset about is not seeing the world’s last Blockbuster store.

I certainly love Netflix, but it would have also been quite the throwback to walk into a real Blockbuster store just like when I was kid.

But, alas, we had to hit the road. (Don’t worry, we not only made it to the Bend Blockbuster a year later, we moved to Bend altogether for a few months!)

There are a couple of different routes you can take from Bend to Portland. Because we were traveling on a holiday weekend, we chose the route with the least expected traffic: through the Warm Springs Reservation and Mt. Hood National Forest.

If we’d had 1-2 days to get from Bend to Portland, we would have likely taken one of these 3 options:

1. Still go the route we took but stop and visit the Museum at Warm Springs to learn more about the three tribes that are represented on this reservation. If possible, a hike in Mt. Hood National Forest would also have been nice.
2. Go via Salem, Oregon, and explore the city there.
3. Take a slightly longer route via Hood River wine country and do some wine tasting there.

Once you get to Portland, settle in and go explore the city.

We met up with friends at the very eccentric Modern Times for beer flights (make sure to check out the hallway by their bathrooms) before enjoying a delicious tapas dinner at Bar Casa Vale.

To continue experiencing the eccentricity of Portland, we held off on dessert until we got to the Rimsky-Korsakoffee House. Classical music, homemade desserts, kitschy teapots, and some haunted elements make this place a local favorite. (Don’t forget to use the restroom here.)

P.S. There’s not really great camping per se near Portland proper, so a hotel it was for our nights there. The Courtyard Marriot in downtown Portland had an amazingly central location and was nice and comfy — especially after only having a sleeping pad for a couple of days!

Day 5: Explore Portland

And by “explore Portland,” I mean eat and drink your way through Portland.

For your only full day in Portland (at least on this trip), start by having brunch at one of the city’s many delicious restaurants.

Hot tip: put your name down at multiple restaurants that are close to each other and take whichever table is available first. One trio to consider: Cheryl’s on 12th, Gracie’s, and Tasty & Adler.

Then spend the rest of the daylight hours alternating between exploring arts districts and trying out new breweries.

For our Sunday in Portland, we hit an art festival in the city’s Pearl District and had some drinks on 10 Barrel’s rooftop deck. Then it was over to the famous Saturday Market, which is an artisanal market that’s open both days of the weekend.

Next up: Ecliptic Brewing — with its galactic references — and the Mississippi Arts District, followed by the Alberta Arts District and Great Notion Brewing (with its lumberjack art!).

Finally, we wrapped up our night with dinner at Little Bird, the most casual of the Portland French trio that also includes Le Pigeon and Canard.

If you’ve got way more time in Portland or just want to do more than eat and drink, check out my 3-day Portland itinerary. It includes outdoors time, art & bike tours, and more.

Day 6: Cannon Beach & Tillamook

On the last day of your San Francisco to Portland road trip, take a mini road trip within your road trip.

Oregon’s coast is incredibly gorgeous, dotted with small cities that are bordered on the other side by vast forests. Besides Crater Lake, my one other must-do on this trip was to visit the coast.

First up, the town of Cannon Beach. The roads from Portland to Cannon Beach can be windy to the point of hypnotizing, so make sure you’re well-caffeinated and alert for the drive.

Its famous Haystack Rock is as picturesque as you’d expect, though these days you’re less likely to see the puffins that have long made the rock its roost. The coast is beautiful nonetheless, and despite every story I’d ever heard, it can actually be warm along the shores of Cannon Beach.

In town, there are many watering holes. A few suggestions:

• Pelican Brewery for beers, though I’d skip their overpriced food
• Cannon Beach Hardware and Public House was suggested to us, but it was (rightfully) closed when we were there on Labor Day. (And yes, it is actually a hardware store as well.)
• Cannon Beach Distillery for the smoothest rum you’ll ever taste. They also have agave spirits, gin, and their specialty: whiskey.

Then, there’s a fork in the road where you have to make a decision: stay in Cannon Beach and hike the coastal trails of Ecola State Park or go eat cheese and ice cream at the Tillamook Creamery about an hour south. Yep, physical activity or food.

I have two witnesses who will attest that we initially went for the active option. But the lines to enter Ecola State Park was so snakingly long that we (and many others) decided to turn back around…in our case, straight into a world of ice cream joy.

The Tillamook Creamery is a humongous structure that dominates in the town of Tillamook. Its cheeses are sold pretty much all over the country, but there are many ice cream flavors that you can’t find elsewhere.

So unless you’re woefully lactose intolerant, head to the ice cream counter upon arrival and find yourself some ice cream heaven.

Then go inside for a self-guided tour about how the Tillamook Creamery came to be and how they make their cheeses. There are also free cheese samples and a huge gift shop that sells everything you can think of with the Tillamook brand on it, plus various locally made products.

After your visit to the Tillamook Creamery, you may feel a little like the cows that power it. But meh, it’s worth it.

If we had more time, I would’ve loved to take it a bit slower on the Oregon Coast, maybe even stay there a night or two. We caught a glimpse of the sun setting on the coast, and it was magical.

Once you get back to Portland, fit in one more delicious meal — and maybe another brewery visit — before your flight. We went with the famous Portland Thai institution Pok Pok and loved every bite. My mouth is watering just thinking about it now!

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Wishing you a safe and fantastic road trip, whether it’s from San Francisco to Portland or vice versa.

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