Extended Vacation

The Beauty of Oregon

I researched Oregon until I was blue in the face. There were too many intriguing places to see in a one-week trip! In the end, I couldn’t be more satisfied with the route I had chosen but I definitely left with longing to see more. Oregon touched a special place in my heart. It truly was state a filled with nothing but beauty.

This itinerary includes three very different terrains: city, countryside, and beach town. A great mix, if you ask me!

First stop, Portland — the laid back city with great food, friendly people and lots of coffee!  

Place to Stay: Portland Marriot Downtown Waterfront 

The location of this Marriott is ideal. It’s situated in a quiet section of the city, along the Willamette River, but still in walking distance to many of Portlands greatest spots. What was so special about this hotel do you ask? The decor alone was enough to satisfy me! Think modern meets woodsy. As you can see, though the bedroom is sleek, it is accented with tree stumps. Certainly a unique detail!

The stunning river view from the balcony is also a selling point….

Places to See:

  • Voodoo Doughnuts – Probably the most amazing doughnuts you will ever have. My personal favorite….the Maple Bacon Bar (shown below in the upper left corner)

  • The Big Legrowlsi – a low key spot to take a breather from walking around the city to enjoy some cold beer. Samples are just $1 if I remember correctly!

  • La Su Chinese Garden – An authentic Chinese Garden right in the middle of the city – a truly unique experience!

Be sure to check out the Teahouse within the garden walls where they have an entire menu of Chinese tea.

  • The Pittock Mansion –  Definitely worth checking out this section of Portland! If you have a car you can drive to the mansion or if going by foot, you can pick up the MAX Light Rail Service  from several locations throughout the city.

The rail, which operates on a track along the streets, leaves you off in a subway-like tunnel.

After exiting the rail, take the elevator up to the streets where you will emerge into a brand new part of Portland to explore — Washington Park!

Buses run on a fixed schedule for transportation to the areas around the park including the Oregon Zoo, The International Rose Test Garden, Portland Japanese Garden, and Hoyt Arboretum.

The Hoyt Arboretum features a trail through a beautiful forest that leads up to the Pittock Mansion….

….where tours are offered to explore the inside of the mansion and learn about its history.

Not to mention, the amazing view of Portland that the mansion grounds offer 🙂

  • Stumptown Coffee Roasters – Hidden across the bridge of the Willamette River, in the industrial part of the city, you will find Stumptown Coffee Roasters headquarters. This is a must see if you enjoy coffee! Free tastings and tours are offered, where you will get to experience coffee cupping, just like the professionals do! 

In order to get to your next destination a rental car will be needed. Just a few blocks away from the Marriott is an Enterprise found here. While I wouldn’t recommend walking, especially with luggage, this ride is nothing an Uber can’t handle 🙂

We opted to return the rental at a different location, which was a bit more expensive, but it saved us a trip back the original Enterprise and allowed us to go directly to the airport at the end of the trip.

Next Stop – Willamette Valley: Bring on the Wine! 

Do you fancy yourself a glass of Pinot Noir? If so, you will want to be sure to make a stop in the Willamette Valley which is known for this specific type of wine. Not to worry if you prefer white wines because the valley contains more than 500 wineries.  Obviously, it’s impossible to visit them all in one trip, but I can make some recommendations.

 Place to Stay: Chehalem Ridge Bed & Breakfast 

Everything about this Bed & Breakfast was charming! Please do yourself a favor and BOOK HERE!!

The room was cozy, quaint, and full of charm. 

The bathroom was spotless and contained a soaker tub, complete with a book rack for reading and robes to stay nice and warm!

The B&B itself is built into the side of cliff overlooking the Valley…

….which makes for another incredible view!

Breakfast is offered daily at 8 or 9 (your choice) and as long as the weather is nice, is served outside on the balcony, overlooking the valley with the crisp, cool morning air.

Places to See:

  • Wineries: Because what else would you see in wine country?! Among the wineries situated throughout the Valley, we only had the opportunity to visit two of them:
  1. Armenta Cellars – This was the smaller out of the two, but the wine was outstanding!

And the tasting room was filled with character…

2. Bergström Wines  – Featured an outdoor porch overlooking the countryside and a waiter service for the wine tasting. It certainly made for a enjoyable tasting experience!


As I mentioned earlier, there are over 500 wineries to explore here! So grab a map, get in your rental car and go explore 🙂

Last Stop, Cannon Beach — rated one of the ten most beautiful towns on the west coast 

And it surely lives up to this title! Every inch of this cozy little beach town radiates beauty. So many times I remember thinking “this can’t be real, it looks like a postcard!”

Place to Stay: Hallmark Resort & Spa Cannon Beach – a family-friendly home away from home!

The Hallmark resort is the ideal place to stay for so many reasons.  Having amenities such as free DVD and popcorn, freshly baked cookies available in the lobby, free cruiser bike rentals, and drinking fountains made just for your dog, they really go out of their way to make you feel at home!

Another exciting feature about this hotel is the comfy bedroom….

….equipped with a fireplace to stay warm on the colds nights….

…and an oceanfront balcony…

…with your very own view of Haystack Rock!

Which brings me to the first “Places to See”…..

  • Haystack Rock (though you really don’t have to go far to see it!) I never thought I could stare at a rock for so long. But as you walk along the beach, each step that you take offers a new and picturesque view.

And its not until you get up close do you realize how massive the rock formation really is!

  • Tillamook Head – Drivable by car, though I believe it can also be hiked, this point raises 1,000 feet above the ocean and was one of the places explored by the Lewis and Clark Expedition in the 1800s.

A quote by William Clark says it best: “I behold the grandest and most pleasing prospect which my eyes ever surveyed.” I couldn’t agree more!

  • Other than the places listed above, the rest of the time in Cannon Beach should be be spent downtown! Shops, pubs, cafe’s and resturants begin almost at the moment you exit the grounds of the Hallmark Resort.

The streets of downtown Cannon Beach are quaint and full of culture….

With colorful flowers…

Art galleries….


Good beer….

And great comfort food.

Also don’t forget to pack a sweatshirt! Nights can feel like winter here…even in the middle of the summer.

And that just about wraps it up! Just a quick recap for easy booking, this itinerary includes:

  1. Portland
  2. Willamette ValleyChehalem Ridge Bed & Breakfast (2 nights)
    • About a half hour drive from Portland to Willamette Valley
  3. Cannon BeachHallmark Resort & Spa Cannon Beach (2 nights)
    • About a two hour drive from Willamette Valley to Cannon Beach, but very scenic!
    • Return to Portland International Airport where you can drop off the rental car and catch a flight back home

If this post inspires you to try out this itinerary for yourself, nothing would make me happier than if you stopped back here and shared your thoughts. I only mark out the spots….it’s up to you to create your own unique collection of experiences 🙂

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