The Ultimate Extended Weekend in Portland, Oregon

“So much of who we are is where we have been”


It’s time for another adventure in a state I have never been to before, OREGON! This marked my thirty-fourth state and another solo adventure. Oregon and Alaska are the two states that have been super high on the list that I haven’t explored yet and thankfully I got to cross one of those off the list!


For this adventure, I’m excited to explore Portland and the surrounding areas, enjoy the great outdoors, try new food, meet new people (one of the best aspects of solo travel), and embrace all that Oregon has to offer! With so many items on the bucket list, I decided to take a few vacation days to really make the most of my time here. Let’s get into the reasons why you should visit Portland, Oregon not Portland, Maine.

The Ultimate Extended Weekend in Portland, Oregon

My overall first impression of Portland was a very active city, free spirit vibes, outdoorsy, kind people, a biking city, plenty of greenery, very eco-friendly, and endless good food. I didn’t have too many expectations going into this trip and learned I really enjoyed the pacific northwest more than I did before this trip. Being active, taking care of your body and the planet, and eating delicious food are things I personally love and are the top few reasons I fell in love with Portland, Oregon. Over the course of about five days, I set out to explore various areas in and around Portland which included a variety of outdoor activities and lots of food. Here are my recommendations of just a few of the many activities and food spots available in the area:

Outdoor Activities (many which are FREE)

1. Latourell Falls

Enjoy the upper and lower Latourell Falls at one of the first stops along the Columbia River Gorge. Parking is somewhat limited, but thankfully I was able to get a spot pretty easily. I recommend getting there earlier in the day for better parking, to avoid crowds, and before it gets warmer in the day. I took the 2ish mile loop trail that takes you up to the upper falls that it an easy to moderate hike with minimal elevation gain. Great views of two waterfalls for such a short hike. Highly recommend this stop! Plus you can easily make the following stops to various waterfalls and hikes as you drive down the scenic highway (much prettier and more peaceful than the big highway just on the other side of the railroad tracks).

The Ultimate Extended Weekend in Portland, Oregon

2. Multnomah Falls

You’ve probably seen a picture of this iconic waterfall on instagram, pinterest, wherever and for good reason. This massively tall waterfall is a short walk from the road and offers a hike to the top of the falls! Get ready for about 800+ft in elevation gain with 11 switchbacks before you make it to the top, but the views are incredible! I highly recommend this two mile hike, just make sure you bring some water and a snack to keep ya fueled up :).

The Ultimate Extended Weekend in Portland, Oregon - Multnomah Falls
The Ultimate Extended Weekend in Portland, Oregon - Multnomah Falls
The Ultimate Extended Weekend in Portland, Oregon - Multnomah Falls

Parking Tip: Arrive early to get a limited parking space or park about a quarter mile up the road at Wahkeena Falls, there is some parking right off the road, but there’s also a picnic area with much more parking (this is where I parked without a problem). Then you’ll hike a small quarter of a mile after viewing the easily viewed Wahkeena Falls.

Driving down this historic highway is a beautiful drive to let down the windows and simply take in the fresh air. Unfortunately due to the Eagle Creek River fires in 2017, many hikes down the road from the first few falls are still destroyed and closed as of the summer of 2019.

3. Cannon Beach + Haystack Rock

If you drive about 1.5 hours west of the city, you’ll arrive at the Pacific Ocean for a beach day! You’ve probably heard of the iconic Cannon Beach or seen photos of the massive Haystack Rock, so now is the time to visit these iconic destinations. Take a beauty drive through the Tillamook State Forest filled with massive evergreen trees lining the drive there. When you arrive, you’ll be able to explore this adorable beach town with a book store, candy shop, glass blowing store, and so much more! Grab a book from the local bookshop and headed for relaxing day at the beach. You might be greeted with some fog and cooler temperatures on the beach, so remember to pack accordingly! I enjoyed the entire afternoon here, took a handful of photos, and read some of my new book! I even met a new photographer friend from the Seattle area and we still keep in touch to this day.

The Ultimate Extended Weekend in Portland, Oregon
The Ultimate Extended Weekend in Portland, Oregon

4. Trillium Lake near Mt. Hood

On a clear day you can see Mt. Hood from various points of the city and naturally wanted to get closer to check it out. I looked up a variety of hikes and many of them were lengthy hikes that take several hours. If you would like a shorter or easier hike, I would recommend hiking/walking around Trillium Lake.

Before exploring a majority of national forest area, you’ll need cash to purchase a $5 pass that you can use for several days. Once you have a pass, you are free to enter past the gates to various hikes and camping locations. Trillium Lake offers a beautiful view of Mt. Hood reflecting on the water and a relaxing walk/hike alongside the lake. There are activities for everyone here including enjoying lunch at picnic tables, going fishing, kayaking or paddle boarding, hiking around the lake, and photography.

The Ultimate Extended Weekend in Portland, Oregon
The Ultimate Extended Weekend in Portland, Oregon

The next three activities are all located within a few miles of each other, so I recommend doing them on the same day to maximize your time in the Portland area. There are so many activities in this area in addition to the following activities including a few hiking trails, The Oregon Zoo, and the Hoyt Arboretum:

5. Pittock Mansion Viewpoint

If you want a great view of Portland, head up to Pittock Mansion Viewpoint! Here you can pay to tour the mansion or simply enjoy the incredible views of the city and Mt. Hood. Bring a few snacks, sit back, and enjoy views like this:

The Ultimate Extended Weekend in Portland, Oregon

6. Portland Japanese Garden

Take a short drive down the road from the Pittock Mansion to Portland’s newly renovated Japanese Garden. This beautiful, picture perfect garden is filled with culture and peacefulness. Take a stroll through these zen gardens and hopefully learn something new about the Japanese culture.

The Ultimate Extended Weekend in Portland, Oregon - Portland Japanese Garden
The Ultimate Extended Weekend in Portland, Oregon - Portland Japanese Garden

7. International Rose Test Garden

Across the street from the Japanese Garden, you’ll find the massive rose garden! I got extremely lucky and happened to visit during PEAK bloom in June. If June doesn’t work with your travel plans, no need to sweat because this garden blooms from April to October, depending on the weather of course. The garden was filled with 650+ blooming roses that smelled so good you just have to be there to experience it.

The Ultimate Extended Weekend in Portland, Oregon - International Rose Test Garden
The Ultimate Extended Weekend in Portland, Oregon - International Rose Test Garden

8. St. John’s Bridge

This bright blue bridge is a key architecture piece of the city that offers a beautiful drive across the water. I recommend driving over the bridge then going to the park just below for sunset or a picnic and more great views of the bridge.

The Ultimate Extended Weekend in Portland, Oregon

9. Powell’s Bookstore

Powell’s is the world’s largest new and used book store with over a million books in the store that occupies an entire block in downtown Portland! Book lover or not, this is an incredible stop to add to your itinerary!

The Ultimate Extended Weekend in Portland, Oregon - Powell's Bookstore

Food: Very Important to Avoid Anyone Getting Hangry on the Trip

1. Bamboo Sushi

As a fellow sushi lover and frequent sushi consumer, I’ve had my fair share of fish in roll form. Bamboo Sushi offers a classy environment with nicer chop sticks rather than the throw away kind, a hip bar, they are eco-friendly, have a good aesthetic (because that’s what the kids are into these days right?), and probably one of the best sushi rolls I’ve had in a really long time. I recommend sitting at the sushi bar where you’ll be given complementary edamame and a tiny cucumber salad. If you enjoy a savory roll or just sushi in general, you should order the Green Machine. This flavorful roll has impeccable flavor, is covered in avocado, is the perfect amount of food to fill ya up, and the combination of flavors will make your mouth and tummy very happy. Make sure to add in the albacore fish to the roll, you’ll thank me later :P.

The Ultimate Extended Weekend in Portland, Oregon - Bamboo Sushi

2. Bye and Bye

Get the Three Liars to Drink and the BBQ Brussel Bowl for your Meal. This is a cute funky bar and restaurant with outdoor seating and delicious vegan food. I’m personally not vegan, but I enjoy eating healthier options when I can so I wanted to try out a vegan meal while in the funky city of Portland.

3. Tasty and Adler

Tasty and Adler is a great stop for lunch or dinner while you are exploring downtown Portland. Yelp led me in the right direction to the modern American steakhouse for a tasty (pun intended :P) burger and fries for lunch. Now to make you a little hungry:

The Ultimate Extended Weekend in Portland, Oregon - Tasty and Adler

4. Blue Star Donuts

A Portland staple here! They have so many different flavors that I’ve never seen before so naturally picked their most popular and unique donuts to fuel up before another hike. There are a few locations around town, so pick the one that is close to you or on the way to a hike and enjoy!

The Ultimate Extended Weekend in Portland, Oregon - Blue Star

5. VooDoo Donuts

Another donut spot that is located in various cities across America and another staple in this donut loving city.

The Ultimate Extended Weekend in Portland, Oregon - VooDoo Donuts

6. Falafel House

Located in a food truck heaven, the falafel house offers flavor-packed and affordable meals that you can enjoy at picnic tables that are surrounded by so many food trucks. This is a great option for a quintessential Portland meal and with so many food trucks, there is something for everyone!

The Ultimate Extended Weekend in Portland, Oregon

General Tips + Remaining Bucket List Items:

  • Rent a car: You’ve got lots of beautiful drives ahead of you!
  • Location / Parking: I recommend not staying downtown since there is plenty of free parking everywhere and odds are you’ll only have a 10 minute drive max to downtown. If you stay downtown, parking will be pricey and tricky to find, but look for a parking garage that doesn’t cost and arm and a leg like hotel valet parking :P.
  • Food: Quirky, delicious, often vegan, food trucks, plenty of wine, and many more! There are endless yummy and unique Portland munchies to choose from, so eat up!
  • Activities: Hikes near Eagle Creek trails, explore the Mt. Hood area more, fly in a plane across Portland, and enjoy all the fun activities in the area! If you come in the spring, the tulips fields are suppose to be incredible and similar to the famous Amsterdam tulip fields! There are so many activities throughout Oregon that would be incredible to experience.
  • Chat with Locals/Fellow Travelers: You’ll make new friends, get incredible food recommendations, and understand the good vibes of Portland, Oregon!
The Ultimate Extended Weekend in Portland, Oregon

I hope to return to this beautiful green state and be able to explore much more of Oregon. This state is filled with kind and active people, great food, endless outdoor activities, great photo opportunities, plenty of beer and wine, towering trees, stunning rose gardens, great views, hot springs, volcanic mountains, the list goes on. I hope this inspires you to book your bucket list trip, a trip to Portland, or simply get outdoors!

With wanderlust,

Haley

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