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The Perfect Oregon Itinerary (With Maps!)

Updated: Aug 14, 2021

We were given an opportunity to take a kid-free vacation for the first time since having children so we jumped at the chance! I didn't want to go too far or be away for too long, so we thought exploring Oregon would be the perfect trip for us. Our kids are still small and hiking long distances just isn't feasible at this stage of life. We loved Oregon so much and I'm so glad we decided to explore the beauty of this state. Below is how we spent our 5 day/4 night trip -

Our go-to's for vacation bookings are, Kayak, Expedia, Priceline, or Travelocity. I'm a bargain shopper always so check them all and find the best deal for you. We decided to stay at a central location and chose a hotel in downtown Portland (The University Place Hotel). This was a bit of a strategic choice on our part; we knew we weren't there for a relaxing, luxury trip. We were there to hike and explore and spend very little time in the room. Hotels in Portland are not cheap so when we chose a budget hotel.... well, it wasn't luxury by a long shot. But that's not the point. The beauty of the state was what we were really there for. Of course, we had to rent a car so we rented through prior to our arrival and picked up our car at the Portland airport.

After checking into the hotel, we spent our first day heading out to the Oregon Coast. It was about an hour a half drive one way with spotty cell service, but the scenic drive was all we needed. We wanted to see Haystack Rock, Cannon Beach, and Ecola State Park so that was our first stop. It was misty and cold on the beach that day (we went the first week of August). I grew up with East Coast beaches and the Oregon Coast was a bit of a culture shock. I'm not sure we saw real sunshine our entire trip, but the dreary atmosphere was kind of magical in a way.

After taking in the views of the coast, we stopped at Pelican Brewing Company at Cannon Beach for dinner and drinks. I have to say it was one of the best burgers I've ever had! The restaurant was beautiful with a ton of windows and so many craft beers to choose from. I'd recommend visiting here before you leave Cannon Beach.

Day 2:

We were quite ambitious on day 2 of our trip. We headed west from Portland to Silver Falls State Park and hiked the Trail of Ten Falls first. I'm from the mountains of West Virginia and am generally quite active and in good physical shape. This trail was NOT easy. Be prepared/warned. I believe you can choose to do only portions of the trail but since we were only in Oregon for a few days, we decided to do the entire trail which was 7.4 miles and not a flat/easy 7.4 miles either. We wore hiking boots and I'm glad we did. There were other people wearing tennis shoes and I think that might have been efficient as well, but some of the areas were rugged and some were wet because of the waterfalls. Traction is best in my opinion. The trail was absolutely stunning! If you are physically able to do the whole trail, do it. And take a good camera too!

After we left Silver Falls State Park, we headed to Tamolitch Falls to hike to Blue Pool.

The hike to Blue Pool was much easier and shorter than Silver Falls, about 2.2 miles in each direction. The trail ends in this unbelievable pool of bright blue water (hence the name). The water is so clear that it almost looks shallow but the pool is actually around 30ft deep. We saw many cliff jumpers while we were there. We weren't one of them though. The hike from the trail down to the water was EXTREMELY steep and the water is very very cold. It was a hard pass from me. The view was enough to make this one of my favorite hikes of all time.

So that was day 2, almost 12 miles of hiking! We headed back to Portland and promptly passed out. On to day 3...

Day 3:

We went exploring Mt. Hood on day 3 of our Oregon trip. First, early in the morning, we went to Trillium Lake Trail to hike, paddleboard, and take photos of the iconic Mt. Hood. It was such a beautiful sight. It almost didn't look real; the blue lake, the clear skies, the snow top mountain... just gorgeous! The loop trail around the lake is less than three miles and flat, sooo much easier than the previous day's hikes. Doesn't it look like a postcard?!

(excuse the arm/phone behind the back in most of these photos; I didn't have a remote shooter and had to use the Canon app ;) )

After a morning at Trillium Lake, we needed what every vacation needs.... A WINERY!!! I cannot express how much I loved this part of our time in Oregon. We went to Mt. Hood Winery and had such a magical time. The winery sits up on a hill, as most things do in Oregon, but the grounds are so green and you're surrounded by a vineyard with Adirondack chairs and hydrangeas with views of Mt. Hood.... it doesn't get any better. The winery is beautiful and the staff seems so happy to be there and work there and have you taste their wine. We sampled multiple wines and didn't find a single one that wasn't amazing. We purchased three of our favorites when we were leaving to take back to the hotel with us. You can also visit their website and have bottles shipped which I have done for a recent wedding anniversary. It's a really special place so don't miss a chance to visit!

Day 4:

We chose to go back toward the coast and see Ecola State Park, hang out on Indian Beach, and visit another local brewery in Cannon Beach. It was another dreary Oregon Coast day but still perfect. We got to Indian Beach early, around 9 am, and apparently, that is a great time to capture pictures of starfish and clams on the shore! I had never seen anything quite like it.

Day 5:

We stayed around Portland on our last day and walked around downtown to shops and local restaurants before heading to the airport. Not too exciting on the last day but we had a very full few days of exploration behind us.

Oregon has a very special place in my heart. I have no roots there. I know not one person from Oregon. I have no ties or reason to be attached to the place but yet I am attached after just one visit. It was almost an other-worldly experience for me. Maybe it was because the Oregon coast was the first place that we were able to be together as a couple, as married people, as the people we were before kids, in over 3 years. Maybe the scenery reminded me slightly of my home in the West Virginia mountains. Maybe it felt slightly like being in a live version of a Twilight film. I'm not totally sure what drew me in so much; probably all of the above. I'm typically a Caribbean beach all-inclusive girl when it comes to vacations as you can see in my other posts, but I cannot recommend taking a trip like this enough. It was stunning to see God's creation in ways that I hadn't had the chance to. There was no time for phones or media of any kind. There was only time to spend with each other, enjoying the beauty around us. And that made Oregon even more magical to me. Until next time Oregon! We'll meet again soon.

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