Oregon – Day 1

Let’s kick this Oregon trip off with a quick itinerary, and a dive into day 1!

Overall itinerary is this in short.

Day 1 – Fly to Portland – Do some hiking – Multumnuh Falls – Check into Hotel – Eat & Drink.

Day 2 – Mt Hood – Hike – Eat – Hike – Canoe Trillium Lake – Hike – Eat & Drink – Hotel in Portland

Day 3 – Cannon Beach – Hike – Bike – Eat & Drink – Hotel on Cannon Beach.

Day 4 – Start 2 Day drive down the Oregon Coast – Views – Brews – Wines – Hikes – Eat.  Hotel at Cape Kiwanda

Day 5 – Continued drive down the Oregon Coast – Views – Brews – Wines – Hikes – Eats – Hotel in Coos Bay.

Day 6 – Head into Wine Country – Hike – Tokatee Falls – Watson Falls – Eat & Drink – Hotel outside Crater Lake.

Day 7 – Crater Lake – Hike – Look – Hike – Look – Eat & Drink – Hotel in Medford, OR

Day 8 – Fly Home

Let’s kick it off with some Day 1 Pictures!

Ok, so we’re off!  Thankful for Josh Schneider who gave us a ride to the airport in the morning.  Now, you should know this about Josh…  he gets up early for only 2 things…  Golf, and The Cleveland Browns.  As sad as that is, it’s the truth, so we’re very grateful to become one of 3 things he’s willing to get up early for.

We traveled pretty light, 2 backpacks, and 1 suitcase.  We planned pretty well, but we really had no idea what it was going to be like.  We knew it was supposed to be nice in Oregon, but we were in what they call in the Pacific Northwest (PNW) a “Shoulder Month”.  Which is essentially May, and part of June, where it’s transitioning from being very wet, rainy, and cold, to warm, and summer temps.

Our plan was to land, get our car, and literally head right into the Columbia River Gorge to hike, and see Multnomah Falls.

I get to our National Rental while Lindsey waited for our bags, and I happen to see a couple Audi’s, BMW’s, Infiniti’s, etc.  I casually ask, what does a guy have to do to get into one of those?  They explained that if I had an “Intermediate” reservation, and I was a part of “Emerald Isle” I got a great discount on these type of vehicles.  I quickly signed up, and went in to talk to someone about my reservation.  In conversation, I mentioned that it was our 10th Anniversary.  With no hesitation, we got ourselves a FREE upgrade to one of those fancy vehicles.  We picked an Audi Q3, and then when we went out, they upgraded us further to the Audi Q5.  She was a beaut, and had some good punch to her as well!

Anyway, we headed out east along the Columbia river which seperates Oregon from Washington.  First, we’re overtaken a bit by the lushness of the trees, and the sheer size of them.  Being from MN, we’re plenty accustomed to a green environment, and trees, but the situation here was quite overwhelming already.  The trees were gigantic.  It felt a little prehistoric as we started looking around.

We drove around a bit, and honestly, it wasn’t that easy to find where we were going.  We later found that there was a bus that takes you from end to end of the scenic areas in the Columbia River Gorge.  I think we hesitated to do that, because we tend to like to get off the reservation a little vs. going with the crowds.

In the end, I think because of our time constraints on day 1, we would have used that service.

So…  we wasted a bit of time, but then found an AWESOME brewery.  Thunder Island Brewing.  We grabbed some lunch, and a few beers.

Let’s pause for some pics!!!

So, a meatball sub, and a couple beers should do the trick!

We set out sights on Multnomah Falls next.  It was, and it wasn’t what we expected.  The falls were magnificent!  But it was very close to the road, huge parking lot, and about a .1 mile hike.  Haha!  Couldn’t have been more tourist-y, but none the less, we loved our first Oregon Waterfall.  It was on, and off raining here, so we had our rain gear.  I’ll chat about the gear we were wearing in a bit.

More Pics!

Gear!  Something that has to be talked about, and is pretty much essential for taking trips like this.  I’m going to cheat a little, and tell you that we literally wore the same thing every single day!  The key to Oregon is layering.  We experienced 25 degrees, up to 90 degrees in 7 days.  We carried packs most of the time, so everything needed to be packable.  Here’s what we wore daily.


  • Nike DriFit T-Shirt
  • Arcteryx light thermal zip up long sleeve.
  • Arcteryx Rain Jacket
  • Prana Zion Stretch shorts.
  • Good pair of hiking socks
  • Keen Targhee Vent Hiking Shoes
  • The North Face ripstop hat.


  • Nike DriFit Shirt
  • Arcteryx light thermal zip up long sleeve
  • Marmot Rain Jacket
  • Stretchy pants/knicker type things (I have no idea.)
  • Hiking socks
  • Keen High Top Boots.

Now, of course, we did shower, and look presentable a few nights out to dinner.  Especially with how epic a shower felt on most days after adventuring.

We decided that we saw enough today, we were getting pretty hungry again, and a bit tired from the travel, so we headed to Portland, which was about 1.5 hours or so from where we were.

We got to Portland, and headed to our hotel.  It was Hotel Rose – A Pineapple Hotel.  This was really confusing to me, and every time I looked it up, I didn’t understand what the hotel name was, or if it was a dump, or something cool.

We were VERY pleasantly surprised!  What a RAD, and very Portland hotel this was!  The creativity of the design, and the textures everywhere were so cool!  Great little bar in it as well.

Turns out the Pineapple has a meaning..  Home, Hospitality, Warmth, Welcome, and Friendship!  (Sounds like a good next tattoo!).

Beds were SUPER comfy, and we also each got our own Duvet (I think that’s what it’s called?) or Huge Comfy Down Blanket.  That’s what I’ll call it.

Check it out!

Obviously, we hit up a couple of breweries…  you know to carb load for tomorrow.

Back Pedal Brewing was pretty cool, very warehouse feeling.  They had a couple Pedal Pubs running as well, which makes a lot of sense based on the name.

After that, we went to 10 Barrels Brewing, which was a little bigger of a brewery/restaurant.  Great beer, and good food for sure!

Thanks for reading, hope you enjoyed!

Please share your comments, thoughts, questions below!

Thank you!

7 thoughts on “Oregon – Day 1

  1. Rachel says:

    Great stuff! Our first trip down the Oregon coast was in the cutlass convertible…you’ve explained the sights perfectly…the waterfall seemed like heaven on earth along with everything else. My son lives in Oregon and his first impression too was “This is God’s country”…so beautiful. We’ve obviously made many trips out there since Jeff lives there…we love the coast, Newport is fun, the lighthouses, the dunes, and we’ve also traveled down the coast in our Ford truck with camper…down to the Redwoods and camped with Jeff. Our trips o Oregon never get old and thank you Cail and Lindsey for packing tips and ideas for new stops. Common Man Guide! Well done!

  2. Luke says:

    Gregory pack, Arcteryx jacket, Prana Zion shorts…dang! This dude knows how to shop gear! Looks like a great first day!

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