Travel Guide: 7 Days in Oregon
Intro
My only knowledge of Oregon growing up was from my favorite computer game -- The Oregon Trail. After visiting Oregon, I know why settlers were risking snakebites and dysentery. Oregon is a beautiful place and we really enjoyed our road trip through the state! It felt like 4 trips in one as we went from the city, to the beach, to the mountains, and finished at snow-covered Crater Lake. I also picked out about 10 coffee shops for Rebecca to choose from, so she was in coffee heaven (and caffeine overload). We had such a great time on this trip! I love that I get to share everything we did and I hope it helps you plan an equally amazing experience.
Before You Go
Weather
We were told that March might not be the best time visit Oregon. If it wasn’t raining on us, it could possibly be snowing which would impact traveling and driving conditions on certain roads. We decided to still visit in March and make the best of whatever weather we experienced. To make planning our routes easier, Oregon’s Department of Transportation offers an amazing website called TripCheck which offers a complete map of road and weather conditions across the whole state. On our days where we were driving over great distances, we would always look at this map to check on road conditions. I also researched a lot about putting tire chains on rental cars. Most people advised against it, but I read that some Oregon roads require you to carry tire chains. We made sure our rental car had 4WD in case we encountered snowing or icy roads. Once we picked up our car, it turned out the Subaru we rented did not have the capacity to fit tire chains. Luckily, we never got into a situation where we needed them.
Reservations
We stayed at Airbnbs on all of our stops and had great experiences with each of them. If you’re interested in trying it out for the first time, use my link for your booking and you will get $40 off your home booking and $15 to use toward an experience worth $50 or more. We chose our 4WD rental car using Priceline.
Packing
Because our itinerary was so varied, we had to pack a variety of clothes. We packed cute clothes to wear in Portland, hiking clothes for Smith Rock State Park, and warm clothes for snowshoeing at Crater Lake. Make sure you bring a rain jacket and waterproof shoes -- you’ll definitely need them.
Our 7 Day Itinerary
We arrived at PDX late in the evening, picked up our rental car, and headed to our Airbnb for the night. It was a cozy studio in Southeast Portland and the perfect place to rest our heads before our next day of exploring.
Day 1: Portland
Powell’s Book Store
Eat breakfast at Pine State Biscuits
Take the “Essential Portland” with Cycle Portland
Bike tours are one of my favorite ways to explore a new city. You’re able to move quickly through the city while also learning about what you’re passing. We were the only two people on our tour and I really feel like we got a good education about Portland.
Eat lunch at the food trucks on Alder Street
We split a sandwich from The Grilled Cheese Grill and chicken and rice from Nong's Khao Man Gai
Grab coffee at Stumptown
Flip through the selection at Powell Books
Browse the interesting stores in Downtown
Some of the ones we went to include Canoe, Alder & Co, Crafty Wonderland, Union Way, Poler Stuff, and Beam & Anchor
Another coffee stop at Heart Coffee Roasters
Eat dinner at Pok Pok
I read so many amazing reviews for this place and also how the line can be a mile long, so we ate there for an early dinner. The initial smell of fish almost caused Rebecca to call it quits before dinner. (She also didn’t love that the house speciality was fish sauce wings.) After our first bites into those wings, there were no regrets. All of the food was very good, but I still dream about those wings and Rebecca was made a believer!
Stop at Salt and Straw for some after dinner ice cream
With interesting and delicious flavors, I would highly recommend treating yourself to this dessert spot!
Day 2: Columbia River Gorge
Eat breakfast at Screen Door
Three words: Chicken and Waffles
Drive through the Columbia River Gorge and stop at the following places:
Portland Women’s Viewpoint
Vista House Crown Viewpoint
Latourell Falls hike (2.4 miles RT)
Bridal Veil Falls hike (0.6 miles RT)
Multnomah Falls viewpoint
Real Talk: When I was planning this part of our trip, I was reading blogs and picked out about 5 hikes that looked so incredibly beautiful that I didn’t know how I was going to choose. It was during my research I started to read about the Eagle Creek Fire of 2017 that destroyed nearly 50,000 acres in Washington and Oregon, including parts of the Columbia River Gorge. Many of the hikes I wanted to go on were closed until further notice. Before planning any hikes, make sure they are open (or find other hikes) using this website.
Eat lunch at Por Que No
Coming from Texas, I feel like we are Tex-Mex experts and this place met our taco standards!
Have a Blue Star Donut for dessert
We decided to try a Blue Star Donut because we had already tried Voodoo Donuts in Austin. Talk about fancy flavored donuts! As fancy as they were, they were equally delicious. They serve flavors like lemon lavender and rose chocolate.
Coffee break at Case Study
Visit St. John’s Bridge and Cathedral Park
Drive to Pittock Mansion for a beautiful view of the city
On the day we went there wasn’t a cloud in the sky, so we had a great view of Mt. Hood and Mt. Saint Helens.
Eat dinner at Apizza Scholls
Option: Attend an open-mic night at the Helium Club
Rebecca and I had planned to attend this, but we were so tired from the day, we decided to skip it.
Day 3: Cannon Beach
Eat breakfast at Upper Left Roasters before leaving Portland
Drive to Cannon Beach (85 miles/1.5 hours)
Visit Echola State Park
Indian Beach Trail -- The last part of the trail was closed when we went, but even so, the first half still offered amazing views.
Visit Haystack Rock
Eat lunch at Tom’s Fish and Chips
Browse the cute shops in town
Options back in Portland:
Japanese Garden
Portland Art Museum
International Rose Test Garden
Aerial Tram
Real Talk: My dad’s cousin lives in Portland, so I met her at Petite Provence Boulangerie & Patisserie for the most delicious fruit tart I had ever had while Rebecca edited pictures at Good Coffee.
Eat dinner at McMenamins Kennedy School Hotel
A former school converted into a hotel with a restaurant and bar – can you get anymore Portland than this? We had a great time eating dinner and then exploring the old school hallways.
Day 4: Painted Hills
Eat an acai bowl for breakfast at Kure Juice Bar and grab a coffee at Groundwork Coffee before leaving Portland
Drive to the Painted Hills (200 miles/4 hours)
Optional stops along the way that offer a beautiful view of Mt. Hood:
Jonsrud Viewpoint
Trillium Lake at Mt. Hood (The road was closed for winter.)
Eat lunch at Tastee Treat in Prineville
We needed lunch and this cute little burger joint where you sit at the counter hit the spot!
Optional trails at Painted Hills:
Painted Cove Trail Loop (0.25 miles)
Painted Hills Overlook Trail (0.5 miles)
Carroll Rim Trail (1.6 miles)
Real Talk: The day we visited the Painted Hills, it was WINDY and not the most pleasant day. We didn’t stray too far from our car, but we did get some good pictures.
Drive to Terrebone and spend the night at this Airbnb
If I was to ever be an Airbnb host, I would want to be Linda from this Airbnb stay. The refrigerator was full of snacks, the place was cozy and inviting, and she even had a day pass Smith Rock State Park that we could use. She was an amazing hostess.
Eat dinner at the Pump House Bar and Grill
This place was ok. If you have time and want a better dinner, I might drive into Bend for more options.
Day 5: Smith Rock State Park and Bend
Grab coffee at the Java Rock drive-through
Hike Misery Ridge at Smith Rock State Park (5 miles/3 hours)
It wasn’t that miserable. It’s only the stairs at the beginning that might be “breathtaking” before the real breathtaking views.
Eat lunch at Spork in Bend
Coffee break at Thump Coffee
Options while you’re in Bend:
Pilot Butte Park Scenic Viewpoint
Old Mill District for Shopping
Tumalo Falls (The road was closed for winter.)
Newberry National Volcanic Monument
Check into your Airbnb
Dinner at 10 Barrel Brewing East Side
If you are a beer drinker, there was a large selection to choose from and the pizza was very good.
Day 6: Crater Lake National Park
Real Talk: This part of our itinerary gave me the most anxiety. With an annual average of 43 feet of snow, Crater Lake is one of the snowiest places in United States. Highway 62 and the road to Rim Village (Munson Valley Road) are plowed and open all year. However, snowy and icy road conditions can occur and may result in temporary road closures. Even if the roads are open, the lake may not be visible due to heavy cloud cover or storms. I made our reservations for a free snowshoe hike with a park ranger knowing that it might not happen. When I checked the park website and webcams the weekend before we left, the road was closed... I didn’t have much hope for our weekend. After lots of prayer (and checking the website a million times that morning), it showed the roads were clear. Even better, the view of the lake was completely clear. This was all seriously a miracle and the cherry to top off our trip!
Breakfast at McKay Cottage Restaurant
Drive to Crater Lake (141 miles/3 hours)
Check in for the tour and grab a quick lunch at the Visitor Center
Snowshoe with a Park Ranger
This was truly a magical experience. I don’t think I will ever get over being able to snowshoe around Crater Lake. If you’re able to do this, I would recommend coming prepared by wearing waterproof pants and shoes. I saw a few people wear jeans and tennis shoes and they did not look comfortable on the hike. You’ll need to be in average shape to complete the hike. It’s nothing strenuous, but moderately physical.
Drive back to Portland (283 miles/5 hours)
Stop for dinner in Eugene or Albany
Spend the night in Portland at a hotel
We stayed at the Courtyard by Marriott close to the airport
Day 7: Fly back home
That’s it!
We truly had a wonderful time in Oregon -- with the help of amazing weather. Even if snowshoeing hadn’t worked out at Crater Lake, I think we still would have enjoyed our time in this beautiful state.
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