First-Timer’s Guide to Oregon

Date
Aug, 19, 2019
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First-Timer’s Guide to Oregon 

I’m a sucker for the travel articles in airline magazines that feature itineraries. These 3-5 day adventures always get me dreaming of the foods and sights I may someday eat and see. Can planning a vacation be a hobby? Travel planning is one of mine. 

As our family’s travel agent – it’s a task I take seriously. For me, the joy of travel is partly in the planning – finding the best restaurant in a little town or the out-of-the way sight that makes me feel like we’re in-the-know. Sometimes traveling on the well-beaten tourist path can be fun but finding gems and feeling like a local is what makes these vacations extra special. Here’s my ode to the quintessential airline magazine travel article – four (or six if you include travel time) days in Oregon. 

Arrival

We took advantage of the last two weeks of the kids’ summer vacation. On a Wednesday, after a half day of work, we took a later flight and arrived at PDX at 5:30 pm, picked up our car from short-term parking thanks to Turo and went to dinner in downtown Portland’s Pearl District. Our main destination was 10 Barrel but after parking outside the Keen headquarters (so cool and outdoorsy you can even buy their sandals from a vending machine out front) we learned 10 Barrel would be a 1-hour wait for dinner. Although I was already thinking about the beer I was going to order we quickly pivoted (because pivoting when necessary makes for a much happier family trip) and walked down the street to the Cha Cha Cha Taqueria for mole enchiladas and a grapefruit margarita. After dinner we drove the 90 minutes to Oceanside on the Pacific coast. Driving in the dark – our only views were the huge, looming evergreens bordering the side of the road and a couple of deer. We arrived at 10:30 pm with two sleeping kids in the back. Deep breath – the stars were out in force and we could hear the waves. We arrived. 

Day 1

Our only agenda – enjoy the gorgeousness of the Pacific Northwest. I was the first to wake-up – too excited about our beach house and living on the water for two days. Wrapped in a blanket I sat in total peace with a cup of coffee on the deck. Seriously, Oceanside was so quiet – the roar of the waves was the only sound. Once the kiddos woke-up we headed to the beach in our pajamas – only meeting a few early-rising dog walkers along the way. We spent the day on the beach – looking for sand dollars at Oceanside State Beach and chasing the waves and building a sand castle at  Short Beach (a little beach off the beaten path) down the road. We also stopped at Cape Meares State Park to see the lighthouse (one of only two lighthouses in the U.S. that is eight-sided) and the octopus tree – a three-hundred year-old tree with 7, 8 or 9 limbs extending from the base (depending on who in our family was counting). We ended the day with Tillamook ice cream cones at the Three Arch Inn (yes, ice cream before dinner because it’s vacation) and dinner at Roseanna’s Cafe where my 10-year was inspired enough by our surroundings to order the sauteed rock shrimp instead of a hotdog. He counts it as the best meal of the trip. 

Day 2

We kept a good thing going and repeated our day one morning. Our beach exploration included a long walk through the Oceanside State Beach tunnel to find an utterly secluded beach – with great views of the sea birds and stacks in the water. Again, the only sounds were the waves crashing. After saying goodbye to our beach house we went south to Pacific City – climbed the sand dune at Cape Kiwanda, chased the waves on the beach, ate halibut tacos at Ben and Jeff’s Burgers and Tacos and shopped at Moment Surf Co. We took a route that wound us through Willamette Valley wine country on our way back to Portland and stopped for a wine tasting at Trisaetum Winery in Newburg. There we enjoyed the fine art gallery that features paintings by the winery founder. The dry riesling and pinot noir were delicious.That night we had a lovely dinner al fresco on our friends’ deck in Portland.

Day 3

On our third full day we road tripped to Mount Hood – destination: Timberline Lodge. If you’re an adult this is an easy 90-minute drive. When you’re a kid – a tree is a tree so it was a little long but the destination made the drive worth it in the end. We walked through the lodge – passing hardcore snowboarders (yes, in August they were going to the very top of Mount Hood where the last snow remains to board), mountain bikers and hikers. We did a short, 3-mile hike on the Pacfic Crest Trail – which after reading Cheryl Strayed’s Wild many years ago always fascinated me. As I explained the amazing hike many people take each year – we actually met a couple of hikers on their 2,100th mile – hiking from Mexico. They started in April and were getting closer to their final destination in Canada. They were tan, with strong legs and light packs and didn’t mind chatting with us for a few minutes about their journey. After we wished them luck our short hike seemed a little easier as we marveled how they carried all their supplies on their backs and had glaciers to overcome in their near future. We eventually made our way down the mountain and stopped for lunch at the Zigzag Mountain Cafe – a staple since the early 1900s. If we didn’t know better we would have thought we landed in a remote Alaskan lodge. We all opted for breakfast fare and my veggie scramble with avocado was filling. Our day ended with an adults only, take-your-time, multi-course dinner at Renata in Portland’s Eastside District. My cocktail, Resting Beach Face, was one of the highlights of my meal along with the stone fruit salad and Fritto Misto. 

Day 4

Our Portland friends recommended the Labyrinth Hike near the Columbia River Gorge but we opted for the more populated tourist trail on old Highway 30 – taking full advantage of what has made this scenery so iconic. Although very busy, we stopped at Vista House, Latourelle Falls, Bridal Veil Falls and Multonomah Falls. We ventured 30 miles further to Hood River and spent a gorgeous afternoon in the waterfront park, a cool outdoor space with several alternative play structures for kids. The kite surfers and wind surfers were out and the river looked like a postcard with all of the colorful sails and kites. We stopped for a local brew and woodfire pizza at Solstice Woodfire Cafe and drove across the bridge to Washington state so the kids could put another pin in our map. That evening we checked in to the Hampton Inn Pearl District and had some down time while the kids swam in the pool. That evening we ran over to Powells Books – for this book lover it was worth the time to see a full city block chock full of books and book lovers. At our final dinner at Deschutes we toasted a full and great vacation.

Departure

Being constrained to your company’s limited paid time off (PTO) policy can really cramp a travel lover’s style. To make the most of our time away from work we planned to work a half day on both ends of the trip. We left downtown just as the sun was rising – the sky pink and the lights still twinkling in the buildings downtown. We had an early morning departure and said goodbye to OR. 

And – like every family vacation – at the end is not a rainbow but …a pile of dirty laundry. Until next time Oregon!

Sarah

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