How to Spend 5 Perfect Days in Portland, Oregon

As a city traveler, Portland has been on my US bucket list for a long time. It has so many things that appeal to me about cities—excellent restaurants, strong pedestrian culture, adorable boutiques—making it the perfect urban getaway!

I knew spending only a few days in Portland wouldn’t be enough to see all the amazing things that the city has to offer. I spent a 5 full days exploring Portland, Oregon visiting several different neighborhoods and even taking a few day trips outside of the city to enjoy the nearby mountain and coastal scenery.

From the artsy northeast neighborhood of Alberta to the unique Japanese gardens in the southwest area, there is something in Portland for everyone to enjoy. Portland has to alot offer, and its proximity to both the coast and the mountains makes it an amazing destination all year round. The summer is the best time to go but the fall and spring are always beautiful.

In this blog post, I am sharing my favorite Portland travel activities to do in a 5 day travel itinerary!

Day One: Rose Garden and Downtown

For your first day in Portland, you’ll be exploring some the famous “must-see” spots in Portland, Oregon including Japanese Gardens, Powell’s Bookstore, Voodoo Donut and the International Rose Test Garden.

West of downtown Portland is where you’ll find the International Rose Test Garden. This is where botanists and scientists test out new hybrids of roses which includes breeding different roses together or breeding roses with other species. Situated on small, easily walkable terraces, the Rose Garden is simply beautiful. Brick lined sidewalks meander through rows of flowers, all of which bloom at different times during the year so you’ll always have a chance to smell the flowers. There are so many unique varieties and colors to explore and my favorite were the magnolia and rose hybrids because they smelled amazing!

If you’ve already made the trek out to the Rose Garden, I definitely recommend stopping at the Japanese Garden as well. With nearly 6 acres to walk, there are several different paths you can take around the park to see all five main gardens. The different gardens are styled in traditional Japanese landscape architectural designs. Of the 5 gardens, there is a tea garden as well as a zen sand and stone garden, which I really enjoyed. It’s a relaxing and tranquil place to wander around. On a clear day, you can even see Mt Hood in the distance!

Once you’re done taking in the garden vibes, head back into the city center for the rest of your morning. Voodoo Donut, a famous bakery and donut shop in downtown Portland, is known for its wacky donut flavors. The bright pink walls and kooky dressed cashiers dancing to punk rock really completed the atmosphere. There is small patio next to the restaurant for patrons to sit and enjoy the donuts and of course, people watch. If you want a full write up about Voodoo Donut, check out my post comparing them to other Portland donut tycoon Blue Star.

Known as a city of books, Powell’s Bookstore is a four story book store that literally covers an entire city block! There is endless opportunities for discovery so you should grab a map when you walk in so that you can navigate where you’re going. It is easy to spend hours in here wandered the towering shelves of books looking at different sections as the smell of books, old and new, fills your senses and brings the store to life. There are lots of nooks with vintage couches to enjoy a few pages of your newest purchase, or relax as you decide which section to visit next!

Day Two: Day Trip to Oregon Coast

Needing a break from the hustle of Portland, the Oregon coast is only an hour drive from Portland, making it the perfect day trip from the city. Start with a visit to Haystack Rock in Cannon Beach. Just offshore from a wide expanse of beach, Haystack Rock is a famous freestanding rock that stands solitary in the ocean with waves crashing around it. We were there during high tide, otherwise we might have been able to walk out to it. But it made for a perfect spot to enjoy a beer and relax as you people watch people coming to take selfies and Instagram shots of the famous backdrop.

Continue your drive along the coast to Devil’s Punchbowl (or Devil’s Cauldron depending on who you ask). The pounding ocean waves have eroded to create an open roofed cave and amazing gorges along the coast. It was a beautiful spot and we managed to make it there while it was bright and sunny. The roaring sounds of the waves and the bright pops of color from the rock and shrubs made for a lovely view.

You’re probably hungry for lunch at this point and Tillamook Creamery is the perfect place to stop. I don’t know about you, but I realllllllly love cheese. Tillamook Creamery is a famous Oregon cheese-maker with years of experience in all sorts of dairy-related endeavors. At their flagship location, you can eat delicious local cuisine while watching cheese making in process. Don’t forget to save room for a delicious scoop of some of the creamiest ice cream ever! Their massive gift shop has all kinds of unique cheese-inspired gifts to bring home to friends.

Before heading back to Portland, stop by one of the Pacific Northwest’s famous local breweries. There are lots of them scattered along the coast, so there are plenty of options. We opted to try out Rogue Brewing because it is one of our favorite breweries. Their original location is located in Newport where you can get both a brewery tour and sample the full menu in their taproom!

Day Three: Northeast Portland

Portland has a lot of distinct neighborhoods, each with their own flair, shopping scene and food style offering a unique set of experiences in the different districts. For your third day in Portland, you’ll explore the northeast neighborhoods of the city—Alberta and Boise.

Need restaurant recommendations for the northeast part of Portland? My foodie travel guide will have you eating some of the best spots that this neighborhood has to offer! 

The Alberta district neighborhood is a quirky artist area with lots of cute shops and delicious restaurants. While this travel itinerary will include specific suggestions to explore while in Northeast Portland, the Alberta neighborhood is one of those perfect areas for just wandering around and discovering your own hidden gems! 

Did you know that there is no sales tax in Portland? Naturally that means you should shop your heart out! Here are some of my favorite shops that I visited while traveling for 5 days in Portland:

Best Place for Succulents: Digs. A great garden & home décor store, Digs has an awesome selection of cool succulents, including air plants! Plus, they’ll serve you up a free cup of espresso as you walk around.

Best Place for Art & Craft Supplies: Collage. A two store front place, there are so many supplies in here from painting to scrapbooking. It’s fun to wander around and see all the vintage trinkets they’ve collected, like loose scrabble tiles and stray address numbers.

Best Place to Find a Gift for Your Boyfriend: Cord. When I walked in here, I immediately thought of how much Sam would love this place. Cool outdoorsmen books, neat gadgets for camping and a case full of knives all displayed in a modern and easy to view way.

Best Place to Find Cute Handmade Dresses: Amelia. This place has a ton of gamine style clothing handmade in Portland and the nearby areas.  It’s cute and girly and their jewelry selection is surprisingly quirky! (cover photo of this post is from there)

Best Place for Funky Vintage Selection: Bristlecone Vintage.  Just off of Alberta Street, Bristlecone is a hole in the wall place with a well-curated selection of vintage Pacific Northwest style pieces. Think fleece jackets, high-waisted denim and plaid.

The next neighborhood of northeast Portland that you’ll explore on your third day in Portland, Oregon is Boise. The main street in this area of Portland is Mississippi Avenue where you’ll find a dense cluster of shops and restaurants. Similar to Alberta, it is fun to jsut walk around this area and discover spots on your own. A few of my favorite Mississippi Avenue shops are:

Best Place to Find Quirky Art Prints & Cards: Land. Stocked full with handmade, local prints, Land is open early for browsing while waiting for brunch. They’ve got a quirky and eclectic style with lots of cards and wall prints, as well as screen printed Oregon themed tees.   

Best Place for Cool Camping Gear: Worn Path. A great store for your outdoorsy brother or boyfriend, Worn Path offers a log cabin-esque vibe filled with classic but stylish camping accessories and supplies.  

Best Place for Western Style Clothing and Backpacks: Animal Traffic. With a great selection of Hershel Supply Co. backpacks and second-hand flannel, Animal Traffic has a distinctly western-meets-northwest vibe. I went here hoping to find a vintage Pendleton jacket, and walked out with an awesome vintage poncho.

Day Four: Day Trip to Multnomah Falls

A short half hour drive outside of Portland will put you in the Columbia River Gorge. The canyon is extensive, and there is lots of hiking all around the area, both on the Oregon and Washington sides of the gorge. Since I only had a few days in the Portland area, I didn’t want to do any extensive hiking but just off the highway is a beautiful waterfall visited by thousands of people every year—Multnomah Falls.

Multnomah Falls Scenic Area is another perfect day trip from Portland, Oregon. You can see the falls from the parking lot, but if you walk up the short paved path, you’ll get a much more impressive full view of the falls. Multnomah has an upper and lower falls with a bridge that crosses over the two. The upper falls are much longer, nearly 550 feet, while the lower falls are about 70 feet, making this the tallest waterfall in Oregon.

It’s really easy to walk right up to the falls and the bridge. The path is full paved and isn’t strenuous, so it’s great place for a family outing. There are lots of tourists there, so expect a bit of a crowd. Surrounding the paths are Oregon’s beautiful mossy forest and trees, so it’s quite beautiful.

Once up to the bridge, you can continue on for a little bit longer walk. I continued up the trail which leads to top of the upper falls. There are 11 switchbacks, and it takes about 45 minutes to walk up. The overlook itself isn’t impressive because you can’t really see the falls well. I did, however, enjoy a nice view of the Columbia river and gorge. Although it was only a short uphill walk, it was nice to get outside on a beautiful afternoon day and spend some time in nature.

Day Five: Southeast Portland

For your final day traveling in Portland Oregon, you’ll take another neighborhood tour but this time of southeast Portland! There are two key neighborhood areas to explore in southeast Portland — Hawthrone and Richmond.

The Hawthorne neighborhood, one of the most historic areas of Portland, has lots of scenery to enjoy with their many beautiful Victorian homes. The main street, Hawthorne Street, gives the neighborhood its namesake but it also has a fun, friendly vibe that contributes a lot to how people typically think of Portland.

Similar to northeast Portland, this is a great area to just wander around and discover hidden gems of your own! There are plenty of cool shops in the Hawthrone neighborhood where you can spend a few bucks. My favorites were:

Best Place for Friendly & Helpful Staff: Imelda’s Shoes. When I was in Portland on my last trip in 2012, I spent like $400 here on amazing quality leather shoes that I still have and wear today! The staff is really friendly and helpful, and they know their brands so you aren’t stuck wandering the piles to find the best for you.

Best Place to Find Affordable Thrift Style: Crossroads Trading. Gotta give a shout out to my favorite second-hand clothing store! I frequent this shop in Chicago, so I definitely knew I wanted to check out the one in Portland. They’ve got lots of great stuff for a fraction of the price.

Best Place for Reasonably Priced, Trendy Clothing: Sloan. There are three locations, but all serve up an awesome assortment of trendy clothing with a Pacific Northwest vibe at prices that are totally reasonable for what they are selling. I think the Mississippi location might be my favorite, but the one on Hawthrone is also great. I got an amazing plaid poncho here that I’ve been wearing non stop since I got home!

Only a few blocks south of the Hawthrone district you’ll find the more up-and-coming neighborhood of Richmond. The arrival of PokPok in this neighborhood triggered a flow of new businesses and restaurants opening up in this area as people flocked to the now-infamous Asian restaurant. You can see a lot of the buildings along Division street are new construction to accommodate the influx of new residents moving to this area.

Need more restaurant recommendations besides PokPok in Southeast Portland? Check out my food travel guide to discover my 15 favorite restaurants in Portland Oregon!

Since this area is still growing, I’m sure there are plenty of new spots to discover in the area but a few of my favorite shops that I found in the Richmond neighborhood are:

Best Place for an Head-to-Toe Outfit: Adorn. The sales associates at Adorn are friendly, and their easily pair-able separates and accessories make it simple to create a seamless outfit all in one spot.

Best Place for Best Place for Vintage Home Décor: Artifact. A mixture between vintage furniture store and on-trend consignment shop, Artifacts has a little bit of everything. I found an amazing thrifted maxi skirt as well as a vintage table runner. It’s just a fun place to walk around.

Are you ready to plan your city travel getaway to Portland, Oregon? Pin the image below so you don’t forget any of these itinerary suggestions!

Author: Megan Arz

I am a travel and food obsessed Midwesterner living in Chicago and dreaming of the world. I work as a full-time program manager for Greenheart Travel, but I am also committed to integrating the travel lifestyle into my every day routines. I am passionate about ethical travel, meeting new people, creating unique memories and eating local cuisine!

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