The Ultimate Jam Packed 5 day Oregon Road Trip

Since we live in Indiana, we planned our arrival for the night before in order to get a somewhat decent night sleep to start our day early and fresh. My goal was to get to Multnomah falls before the crowds and a 6am car rental pick up was my goal. I knew even arriving on the first flight in, Portland time would put us close to lunch before getting on the road and I am so glad we opted to come the night before (despite a midnight arrival)  

Friday night - arrive in Portland (late)

[We saved money on our rental by opting for a next morning 6am pickup, as well as a 10pm drop off the night prior to our flight home. Both on arrival and departure we stayed at the same hotel just minutes from the airport which came with a FREE shuttle! We also were able to avoid the dreaded early morning car rental drop off scene. The shuttle was a breeze! I do recommend scheduling your return to the airport as the early morning shuttles do fill up]

Holiday Inn Portland-Airport (I-205), an IHG Hotel

@jesstakethetrip

We stayed here on night 1 and 5. No frills, no fuss, clean, comfy beds and minutes from the airport. Comes with a FREE shuttle 24/7. Super convenient getting to and from the airport. FYI the continental breakfast is NOT included and is a cool $16 :/ we opted out

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Saturday AM - pick up rental

0620: Free shuttle to the airport to pick up the rental. I was in and out in under 10 minutes! 

             [TRAVEL HACK: book your car rental through Budget connected to your Amazon prime account and save $$$. You also get a percentage back via Amazon gift card after every rental. I have price compared this route with others and nothing compares]

0700: Breakfast at Cameo Cafe

Cameo Cafe East

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A locals fave - try the steak omelette! Super cute vibes, though the surrounding area/blocks are a little sketch this part of town

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Powell's Books on Hawthorne

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This is the smaller sister of Powells as I found out, but I enjoyed the detour because we met a friendly local at a cool bar who gave us a lot of insider recs

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Straight From New York Pizza (Hawthorne)

@jesstakethetrip

Quick, grab a slice and go or order and sit down. Hit the spot and saved us time on our way out of Portland. I had a whole list of spots to choose from but we were legit spent from the mornings hikes and just wanted to get to the coast so we opted for convenience on this one

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Powell's City of Books

@jesstakethetrip

Book lovers clear your schedule! You could spend an entire day getting lost in here - don't forget to check out the Rare Book Room on the third floor. You will need to wait in (hopefully a short) line for a pass as it is limited to 14 people at a time. I only waited about 5 minutes and the store was quite busy so I think this is pretty standard

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Haystack Rock

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This was our anniversary dinner splurge of the trip and it met every expectation. We even captured sunset (though you had to jog down the stairs to view it from the other side of the inn). The meal was phenomenal and was a seasonal four-course prix fixe menu designed by the famous Chef Aaron Bedard. Many of the ingredients are farm to table. We enjoyed morel mushroom risotto and the lab chops were 10/10. By the end we were so full we had to take our chocolate suffle to go!

Stephanie Inn & Dining Room

@jesstakethetrip

This was our anniversary dinner splurge of the trip and it met every expectation. We even captured sunset (though you had to jog down the stairs to view it from the other side of the inn). The meal was phenomenal and was a seasonal four-course prix fixe menu designed by the famous Chef Aaron Bedard. Many of the ingredients are farm to table. We enjoyed morel mushroom risotto and the lab chops were 10/10. By the end we were so full we had to take our chocolate suffle to go!

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The Wayside Inn

@jesstakethetrip

Across from the beach, fraction of the price compared to the bigger resorts by Haystack formation. We would love to bring the kids here in the future!

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Weasku Inn

@jesstakethetrip

You guys, this was the BEST stay of the trip and I wish we would have had longer to spend here. The cutest little cabin and so much history of the property. The staff were so kind and loved answering all of my questions about the celebrity visits and historic encounters. From Walt Disney to Clark Gable, many have visited this historic stay. The price is unbeatable and for all the extras we just couldn't believe this was the cheapest place we stayed when it felt like so much more! Appetizer hour, smores and cookies in the evening, and omg the homemade breakfast was to die for. We watched three deer settle in for bed right outside of our balcony too :) We stayed in the King balcony cabin. 10/10 recommend

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Holiday Inn Portland-Airport (I-205), an IHG Hotel

@jesstakethetrip

We stayed here on night 1 and 5. No frills, no fuss, clean, comfy beds and minutes from the airport. Comes with a FREE shuttle 24/7. Super convenient getting to and from the airport. FYI the continental breakfast is NOT included and is a cool $16 :/ we opted out

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The Ocean Lodge

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Hallmark Resort & Spa Cannon Beach

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Sleepy Monk Coffee Roasters

@jesstakethetrip

There's a reason this place starts forming a line 15 minutes prior to opening at 8! We jumped in behind about 5 people at 7:45 and by 8:15 am the line was wrapped around the side walk! We tried multiple items and everything was so good. A local recommended to me the bacon & blue cheese scone + add salmon cream cheese and I still think about it to this day... Jordan loved the rosemary bagel + salmon cream cheese and the chocolate cake donut. I grabbed a chocolate GF vegan brownie for later and ended up being a really tasty treat! Coffees hit the spot too :D

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The Horn Public House and Depoe Bay Brewing Company

@jesstakethetrip

Stopped in for a quick beer flight and to hydrate before heading to Newport for lunch. We enjoyed watching a mama seal playing with her pup just outside the window here. There are many fishing charters coming and going from this bay so we enjoyed watching the fish cleaners hard at work too

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Clearwater Restaurant

@jesstakethetrip

We split the salmon burger and the tuna rice cakes. Hear me out because while I love salmon, a salmon burger rates about as low as a hotdog for me but the locals praise it so I gave it a shot and let me tell you it was the best salmon burger I have ever had. The tuna rice cakes were 10/10 too. We opted to sit outside on the deck so we could be entertained by the (stinky) male sea lions and the great views of the bay. Definitely one of my top meals of the trip

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Chetco Brewing Company

@jesstakethetrip

VEGAN only food truck inside this brewery! Now, we are not vegan, however I LOVED the tempeh tacos! Actually quite possibly the best tacos I have ever had. We shared a flight, filled our bellies, and hit the road.

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Taprock Northwest Grill

@jesstakethetrip

This place was prime location for river views and had a good vibe. We were tanked by the time we sat down so we ordered our food to go and enjoyed it back at the Inn. Everything was amazing. Jordan go the beef dip sandwhich and I ordered a massive chicken salad that could have easily fed us both. Both were 10/10

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