One Long Weekend in Oregon - A True Road Trip

A road trip from San Francisco to Oregon was first up on my bucket list upon moving to the West Coast. When memorial day weekend came around last year, it was the perfect opportunity to go. All we needed was camping gear and a car. So without much planning, we hit the road and let the journey unfold.

We planned to spend four days and three nights on the road. Oregon is huge. You can easily spend months exploring, but if your time is limited (like ours was) and you want to hit as many hot spots as you can, the below list is a great place to start.

We started the road trip in San Francisco, drove inland through Oregon, hit the border of Oregon and Washington, and then drove the coast back down.

Below is a breakdown of the spots that we hit, in order.

Day 1

We left around 4:30am to start the day early.

Shasta Lake

This lake is beautiful in the summer time. We went kayaking at the lake head, but you can also rent jet skis, houseboats, etc.

Mount Shasta

You will inevitably drive past Mount Shasta on your way to Oregon (if driving inland). The huge snowcapped mountain makes the drive feel surreal! Make sure to get out and take it all in. We ate breakfast in town at Black Bear Diner.

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Crater Lake

This was by far one of my favorite spots of the trip. It’s deep blue color and clarity is unlike anything I have ever seen. It looks untouched. This is the deepest lake in the United States and a MUST SEE if in the area! Picture below speaks for itself.

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Tumalo Falls

This is right outside the Bend area. Easy place to hit on your way in or out of the city.

Bend, Oregon

Very cute city with a lot of great breweries. We went to Crux and sipped some delicious Stouts.

After that, we took a walk along the Deschutes River, which runs through the city!

Restaurant Recs:

*Side note: I came back here in the winter time and skied Mount Bachelor (photo below). I highly recommend this. Great runs with great views.

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Deschutes National Park

Day one was VERY long, so we were excited to find a place to set up camp in Deschutes National Park.

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Day 2

Mount Hood National Forest

Endless areas to explore here. Pick a spot and wander to your hearts desire!

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Smith Rock

Views on view on views! I highly recommend hiking “Misery Ridge” if you are in good shape. It is extremely challenging, but also extremely rewarding. Come prepared with sunscreen and water! This hike will take a few hours depending on how quick you are!

Make sure to look out for the Monkey Face (photo below on the left)!

You can see some of Oregon’s most famous viewpoints from the top—Mount Hood, Mount Jefferson, Three Sisters, Broken Top and Mount Bachelor.

Trillium Lake

This lake is a photographers dream. Mount Hood is in the background and reflects perfectly onto the lake! We packed a picnic and ate here!

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Camped in Mount Hood forest somewhere…

You have probably picked up on the fact that we had ZERO camping plans and no idea where we were going to sleep each night. We knew we would figure it out, and we did. This definitely created some stressful moments though, scrambling before sunset to find somewhere…but HEY, that was part of the adventure!

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Day 3

We woke up in Mount Hood Forest and drove straight to the border of Washington and Oregon. This drive in itself is an experience with endless views. With each turn, the view somehow got better.

Once we hit the border, we drove along the Columbia River.

The river was filled with deep blue and green coloration. Some people call this area “waterfall heaven” because there are so many beautiful falls to explore here.

Ellowah Falls

This is about a 1.4 mile hike round trip—very doable! This was the only waterfall that we went to, but there are SO many more.

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Portland

After seeing Ellowah Falls, we took a bit of a detour south to check out Portland. We grabbed lunch at this cute Italian bistro and walked around. If I were to do this trip over, I would have cut this out, and I would have spent more time checking out waterfalls on the coast. Portland is an awesome place to visit, but was a bit too out of the way for this trip.

After lunch, we drove west and so began our coastal adventure!

Pacific City

After spending a good chunk of time inland, it was SO nice to get back to the ocean. Pacific City is home to a beautiful beach, with rock formations that are otherworldly. We grabbed a few beers from Pelican Brewery (located right on the beach), climbed up the rocks, and relaxed…

This is great area to meet people. You can drive your car up on the beach!

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Day 4

Day 4 was primarily spent driving back south to SF (down the 1). We enjoyed beautiful coastal views the entire drive—it truly never gets old.

We spent a lot of time in the car this weekend, but got out many times to take in the scenery. We covered a lot of land in a short period of time! Wouldn’t have done it any other way.

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Budget

This is a very easy trip to do on a budget. Because we cut out hotels and fancy restaurants, gas became the biggest expense, which was very doable. Enjoy the nature and pack a picnic everywhere you go!

Let me know if there are any questions!

There are SO many places to explore in Oregon that are not listed. This list just scratches the surface and is a great place to start for first timers. I definitely plan to come back here and will let you know what I discover on the next go around. Hit me up with any question!

Thanks for reading!

Xx,

Nat