Fun 5 Day Itinerary for Portland

Fun 5 Day Itinerary for Portland

Why a long weekend in Portland?

The Portland area offers an amazing variety of things to do! Everyone will be happy when visiting Portland;  Wine, nature, hiking, scenic views, history, cultural interests and weird fun!

Why Ride the Train?

I was traveling from Los Angeles, and thought it would be fun to ride The Amtrak Coast Starlight. I love train rides, and the Coast Starlight is advertised as “One of the most spectacular train routes going through stretches of the Pacific Ocean shoreline, dramatic snow-covered peaks, and lush fertile valleys”.  I definitely wanted to see this…. even if it was going to take almost 30 hours.

I read reviews and most said that the Coast Starlight coach seats were comfortable. Coach is also significantly less expensive than reserving a sleeping car option.  I spent about $150 one way in coach, and a sleeping car is closer to $500.
The process of booking is a bit tricky on Amtrak. It is not the most user-friendly process. You can always use the online chat or even call if you get too frustrated. I took the Metro from the West Side of Los Angeles to Los Angeles Union Staton to save on parking. The boarding process was easy and we departed for the journey. The coach seat was perfect for me, and it was enjoyable & interesting to sit next to a teacher from Germany who was backpacking solo through the United States for a month.Views were breathtaking and it was fun to walk to the viewing car and cafes. Remember to pack some snacks as the food costs add up. Plan on delays. Every review I read mentioned arriving late, and we were no exception arriving 4 hours later than scheduled.

It’s a unique experience and I felt it was not about the efficiency of travel, but more about the sites, the people and the journey.

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Fun Itinerary for Portland Oregon

Fun Itinerary for Portland Oregon

The Accommodations in Portland

I arrived in Portland the next afternoon after 30 hours on the train. We booked the Kimpton Hotel Monaco Portland for our accommodations for 2 nights. It was the perfect hotel choice for Portland with a funky interior design and located in a convenient part of downtown. The Kimpton also offered a bonus complimentary happy hour with food and drinks each evening.
If you enjoyed this long weekend itinerary check out The Brandywine Valley & Delaware Seashore long weekend itinerary

The Fun Outings!

We accomplished a LOT in the 2 full days we were in the City of Portland. Some of the highlights included; First Thursday Block Party in the Pearl Neighborhood, Brunch at Mother’s Bistro , late night donuts at Voodoo Donuts  (home of the Maple Blazer Blunt – donut:) and browsing for books at Powell’s Bookstore .We enjoyed a walking tour of Portland where we learned why residents use the term “Portland Weird” –  The term promotes individuality, expressionism, local art, as well as atypical lifestyle choices and leisure activities.

How did Portland get named? Asa Lovejoy and Francis Pettygrove flipped a coin in 1845. Pettygrove won the coin toss. He was from Portland Maine, so he named it after his birthplace. If Lovejoy had won the toss, Portland would be named Boston after his hometown.

Crystal Ballroom

The Dance Party …Partying like it was 1985

We were on a mission to celebrate, and how apropos when we found an 80’s Dance Party at the McMenamins Crystal Ballroom . If you are an 80’s Kid, this can NOT be missed! We felt like we stepped right back into 1985. We were bummed we did not have the hair or outfits to complete the night.
80's dance party portland

The Crystal Ballroom Portland Oregon

The excellent trip planners Karen & Kate!

The Wine

Every girl’s weekend needs a little Wine Tasting… right?  Next stop was the Willamette Valley about an hour South of Portland for some wine tasting.
Willamette Valley Wine Tour

The Willamette Valley is recognized as one of the premier Pinot noir producing areas in the World. We spent the early part of the day visiting wineries and tasting flights of Pinot Noir. I have visited several Wine Regions for tasting trips with friends, and the Willamette Valley ranks high in my opinion for the beauty and tasting room experiences.
Duck Pond Wine

Enjoying live music at the Duck Pond Tasting Room in the Willamette Valley

More Hotels and Food

Our next overnight stay was the unique  Amity Flats located in the tranquil & quaint town of Amity within The Yamhill Valley. The Inn was originally a Masonic Lodge and beautifully renovated combining rustic elements with cool modern comforts. We dined at The Blue Goat Inn and enjoyed a delicious dinner Influenced by world culinary traditions and local harvest. We wished we could have explored more than one night in Amity.
Amity Flats Oregon

Amity Flats Amity Oregon
The Blue Goat Inn

The Blue Goat Inn Amity Oregon

Getting back to Nature

After a wonderful day and evening wine tasting in the Willamette & Yamhill Valleys outside of Portland, we headed North East to The Mount Hood National Forest. The drive was about 2.5 hours. We broke it up by checking out the scenery and a short hike to a waterfall in the Columbia River Gorge.
Columbia River Gorge

Columbia River Gorge
Wahkeena Falls Loop Tral

Wahkeena Falls
Our next destination was the National Historic Landmark Timberline Lodge dedicated in 1937 by Theodore Roosevelt. You may also remember the exterior of this hotel as the hotel in the movie “The Shining”.  It was such a beautiful drive up to the hotel nestled against Mount Hood at an elevation of 5960 feet. There was still snow on the mountain in August! The exterior and the interior are a gorgeously maintained in a quintessential rustic mountain lodge decor.
Mount Hood

Drive up to Mount Hood
Timberline Lodge

Mountainside view of Timberline Lodge
A relaxing evening was spent exploring the grounds of the Timberline Lodge. Dinner was delicous in the dining room, and the rooms were quaint and comfortable.

The next morning we took a short hike in the Mount Hood National Forest before heading back to the airport in Portland.

​I opted to fly back to Los Angeles rather than a 30 hour ride back on the Coast Starlight:) I am so glad I did it, but 2 times in 6 days would have been a bit exhausting.

Mount Hood National Forest Hike

Mount Hood National Forest

The Take Away

I highly recommend a trip to the city of Portland and its surrounding valleys. It was an action-packed trip with delightful surprises. A small sampling of what the gorgeous Pacific Northwest has to offer.

Published by Judy Hughes

I am a small group trip leader for 2 travel clubs. We check out cool and off the beaten path places around the World. Adventure is our specialty. I love to take notes and share the travel tips with you in my blog! Hope you check it out!