
Nearly every year, we book a trip between Christmas and the New Year. There are a couple purposes to this: 1.) The holiday season can be so busy that it is hard to get quality time with each other during it and this allows that. 2.) Both of us have either light work or no work during that week. But you could do this itinerary (or any of other itineraries scheduled during this break) any time of year.
Now, this particular trip was one of my favorites we’ve ever done for that week. It was a classic road trip (which to me means sleeping in a new city every night) and we really leaned into some of the lesser known towns along the way. This made for exploring some small lodges and motels as well as some fun eateries. We also got super lucky with weather and mostly had clear skies. Once we got to Portland, we were able to enjoy the city for a couple days. This wasn’t my first time to Portland but it was my only time there in the winter.
Highlights on this trip:
- Mendocino the town was as cute as I had imagined it to be. I wish we had gotten a little more time there, but it is quaint, quiet and beautiful.
- Avenue of the Giants: So I didn’t know this before we went, but this is not actually in Redwood National Park, it is actually a part of the state park, yet this drive has a large concentration of the Redwood Giants! So impressive from the beginning to the end. One bonus for us was there was almost no one on the drive with us since we were in the dead of winter. I would imagine in the summer this drive would get pretty packed.
- Fireside Motel in Yachats: first off Yachats is such a cool example of a small, coastal northern California town. I loved the tiny town, but the motel was the true star of this day! It is right on the coast and you can see and hear the waves crashing against the rock. Since it was winter, we got moody weather (no rain though!) so it was perfectly cozy to walk around with hot coffee and explore the grounds of the motel. Highly recommend this spot if you are in the area!
- Day 4 might have been my favorite full day of this trip, but that is mostly because I LOVE cheese! The Tillamook factory is exactly what you would expect, but I loved it. And then Cannon Beach is probably my highlight of all the beaches we explored. It has a long stretch that you can just walk along the beach and enjoy the buttes that this area of Oregon is so famous for.
- Bowling in Astoria: I mean what kind of 80s kids would we be if we didn’t enjoy going to the famous bowling alley featured in Goonies. It is the exact same as the movie which means it is fantastic in kitschy-ness (is that a word?). My bowling on the other hand was not fantastic, but it is always a fun activity in new towns.

Tips/Things I Would Change:
- You will notice that while there are some hikes on this trip, there are far fewer than we usually do. Part of that is because the drive itself doesn’t lend itself to much hiking (see point below) but also a lot of the walking on this trip was done along the various beaches we visited or in the cute little towns. The point of this trip was to enjoy the coast and I think we did that well with this itinerary.
- While I loved the “winter aspect” of this trip because when we went it wasn’t crowded anywhere, being that we were in winter the daylight hours are limited. As you can see from the itinerary, there is a quite a bit of driving each day. This combined with sightseeing made for very full days trying to maximize daylight. I would maybe try to do this trip again in a different time of year with some longer days which would allow some more time in each day to explore or just chill at a cool coffee shop, bar or beach.
- I mentioned it earlier, but I loved all the little motels/cabins we stayed in. Most of the time, we weren’t in a big city but even if we were, we chose small bed and breakfasts or motels. I highlighted Fireside, but honestly I would rebook all of them if we did this again.
- As I mentioned, I’ve been to Portland several times (summer, fall and winter). I think winter is probably my least favorite only because it can be (and was) quite cold and rainy which limits the outdoor activities near to Portland and the walkability of the city itself. I think one night there would be sufficient (or even spending an extra night on the road and arriving into Portland for the flight out).















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