3 Days in Portland, Oregon: A Perfect 3 Day Itinerary!

I recently spent 3 days in Portland, and absolutely loved it! If you’re looking for natural beauty and urban culture with a cool vibe, Portland is the place to be. Known for its lush green landscapes, quirky vibe, and being a stone’s throw away from Mt. Hood, it’s easy to see why Portland is often listed among the coolest cities in the US and Canada. Three days in this fab city gave me plenty of time to explore the area. Whether you’re a foodie, an outdoor enthusiast, or just want to explore a cool city, Portland has something for everyone. Highly recommend a visit!

Welcome to Portland Old Town: The best things to do and see with 3 days in Portland, Oregon.

Here’s how to make the most of a long three-day weekend in Portland

3 Days in Portland – Day 1

Day1: Morning – Wander around Downtown

Visit old downtown Portland and visit Powell’s Books. First, grab a sweet treat at Voodoo Doughnut. You’ll find unique flavors like Bacon Maple Bar and Voodoo Doll, and see what all the hype is about.

visit voodoo doughnuts in Portland

The bright pink exterior adds to the cool vibe, however, the security guard outside, making people wait in line even when the shop was nearly empty (I was literally the only customer with three clerks inside), felt a bit unnecessary and ‘Hollywood’.

things to do in Portland - try voodoo doughnuts

After your doughnuts, head over to Powell’s Books, the world’s largest independent bookstore. There are lots of different rooms and floors to explore, and there’s even a place to grab a coffee. The collection of new, used, and rare books is extensive, and the rare book room on the top floor is particularly special. You can find first editions and signed copies, and almost feel the history as you turn the pages.

visit Powel's bookstore with you have 3 days in POrtland, Oregon

After you leave Powell’s Books, wander around the downtown area, check out the edgy art painted on the side of buildings, and pop into Buffalo Exchange to hunt for treasures. It’s a great way to feel the vibes of the city and maybe find some hidden gems.

Day 1: Lunch – Nong’s Khao Man Gai

A great lunch spot in downtown Portland is Nong’s Khao Man Gai. Nong’s is a local landmark and is famous for their Khao Man Gai (poached chicken and rice), served with a delicious tangy sauce that people rave about.

visit Nong's to try their special thai chicken in Portland

What I loved about Nong’s is the simplicity of the dishes. The menu isn’t huge, they stick to what they do best and don’t try anything fancy. The chicken and rice might sound basic, but it’s far from basic – it’s perfection. Each bite is flavorful and paired with fresh cucumbers and cilantro.

best things to do in Portland - Nong's chicken

Other great options on the menu are the Khao Kha Muu (Thai Pork & Rice ), Chicken, Rice and peanut sauce. If you prefer vegetarian they’ve got you covered with some great tofu dishes, too. Don’t miss the chance to enjoy their traditional drinks menu – highly recommend the lychee margarita, Thai tea float and ginger lemonade.

Hot Tip: The portion sizes are very generous, so be sure to take advantage of the to-go boxes they provide for customers and enjoy your leftovers at home.

best food in oregon

Day 1: Afternoon – Visit the Portland Japanese Garden and Rose Garden

Spend the afternoon at Washington Park, and smell the roses (literally!) at the beautiful International Rose Garden and Portland Japanese Garden.

The Portland Japanese Garden is a beautiful escape from the city and truly one of my favorite spots in Portland. It’s meticulously maintained and the perfect balance of nature and traditional Japanese architecture.

portland japanese gardens

One of the highlights for me was the Sand and Stone Garden. It felt incredibly calming and the raked patterns in the sand are so intricate. We lingered there for a while and then continued to wander.

sand and stone garden in portland

Another special part of the garden is the koi pond – watching the juicy koi fish swimming gracefully together just minding their own business felt strangely comforting. It’s peaceful, picturesque, and the perfect spot to sit and relax for a while.

The Portland Japanese Gardens also host special events and exhibits throughout the year – you can plan your visit and find that schedule here.

visit the japanese gardens in portland

The Rose Garden is adjacent to the Japanese Garden (free admission), and is home to over 10,000 rose bushes. The roses were in full bloom during our visit (in June) and we were able to soak in the fresh aroma of the roses and the views of Mt. Hood.

visit the rose garden when you have 3 days in Portland

Day 1: Evening – Catch a Movie at the Historic Hollywood Theater

End your day at the nearly 100-year-old Hollywood Theater, a nonprofit movie theatre dedicated to preserving the authentic movie-going experience. This historic building focuses on the upkeep and maintenance of the theater, curating an extensive film archive, and showing movies on film whenever possible.

hollywood theatre in portland oregon

They like to embrace the community spirit with 30-40 unique events every month, driven by local filmmakers and community members. We watched Kinds of Kindness and it was lovely to immerse ourselves in the magic of movies in this Portland landmark.

You can find the Hollywood Theater movie schedule here.

3 Days in Portland – Day 2

Day 2: Morning – Hike Forest Park’s Wildwood Trail

(and see the Witch’s Castle and Pittock Mansion)

Start your day with a hike on the Wildwood Trail in Forest Park at the Lower Macleay Trailhead. It’s about a 20-minute drive from downtown Portland depending on traffic.

Hike Forest Park’s Wildwood Trail and see the Witch’s Castle in portland, Oregon

Hike to Witch’s Castle (0.8 miles), and take pics of the graffiti on this stone structure. If you have time, continue on the Wildwood trail (it’s all uphill) towards Pittock Mansion for amazing views of the city (about 2.5 miles total). The mansion is lovely and the grounds were filled with blooming roses.

3 days in portland

Once you’ve soaked in the views, hike back to the trailhead and head down (it’s so much easier on the way back!) and be sure to try some fresh blackberries that line the trail. The total round-trip hike is about 6 miles and you should allow 2-4 hours depending on your pace.

hikes in Portland, Oregon

Hot Tip: This trail gets super crowded, so try and get there early and go on a weekday if possible.

Day 2: Afternoon – Wander Nob Hill and NW 23rd Avenue

Spend the afternoon wandering down NW 23rd Avenue, a charming street lined with boutiques, cafes, and restaurants. Stop for ice-cream or juice at one of the many cafes and just enjoy the trendy Nob Hill neighborhood.

wander around trendy Nob HIll neighborhood

Day 2: Dinner – Eat at Pizza Thief

Portland has plenty of pizza spots, but Pizza Thief stands out. It’s located on the outskirts of the Nob Hill neighborhood. The owners were inspired by their colorful past of stealing pizzas as kids. They decided to create something they love (and that’s legal) – Pizza Thief and Bandit Bar next door. The place has indoor and outdoor seating and is filled with hipsters. Their menu is simple, featuring salads, a couple of appetizers, pizzas, and dessert.

eat at pizza thief in portland

Their pizza is perfection with a perfect crust and interesting toppings. I chose the delish vegan option with tomato sauce, roasted mushrooms, piquillo peppers, kale, mustard greens, Calabrian chili-garlic oil, and Sicilian oregano paired with a crisp pear cider. If you’re a mushroom lover, be sure to try the Wildwood with roasted mushrooms, cream, mozz-provolone, fontal, caciotta al tartufo, and rosemary.

places to eat in portland - pizza thief

Don’t miss their salads, either! The market salad is prepared with whatever fresh veggies they find at the farmer’s market that day, and the chopped salad is the bomb. For dessert there’s the choice of The Closer Cookie, a ¼ lb triple chocolate-hazelnut cookie, The Vegan Corn Raspberry Thumbprint cookie with house-made raspberry jam, and The Cannoli with citrus & chocolate ricotta filling. You seriously can’t go wrong with any of the options.

best pizza in portland - pizza thief

Don’t forget to visit the Bandit Bar for a local beer to go with your ‘za too – they have quite a comprehensive rotating menu of local brews and ciders.  You can now also enjoy Pizza Thief’s delicious pies in the tap room at Great Notion Brewing where you get to pair their locally sourced pizzas with Great Notion’s craft beers.

craft beer and cider menu at pizza thief

3 Days in Portland – Day 3

Day 3: Morning – Drive to Multnomah Falls

Drive out to the Columbia River Gorge to visit Multnomah Falls, a stunning 620-foot waterfall. This takes approximately 40 minutes from downtown Portland. Once you’ve admired the falls from the bottom, you can hike up to Benson Bridge for a closer view and to (literally) soak it all in (about 10-15 minutes). 

hike to Multnomah Falls in portland, oregon

Continue on the trail to the top of the falls if you’re feeling adventurous, it’s a mile up a steep hill to the viewing deck, but the good news is that it’s all downhill on the way back. The views are spectacular of the Hood River, and this was a highlight of our 3 days in Portland.

hikes in portland -

If you have longer than 3 days in Portland you can continue your drive to Hood River, a charming area about 45 minutes outside of Portland. It’s a great spot for windsurfing and enjoying the natural beauty of the Columbia River Gorge.

Hot Tip: Arrive early – at 7.30am it was just starting to get crowded. If you visit between May and September, you’ll need to reserve a timed entry ticket that costs $2 per car. You can find information for that here.

views from the top of the hike to Multnomah Falls

Day 3: Afternoon – Saturday Market

Spend the afternoon wandering around the Portland Saturday Market. It’s the largest outdoor arts and crafts market in the country with over 150 booths to browse handmade goods and unique art products. When you get hungry, there are plenty of food vendors offering everything from gourmet sandwiches to delicious street food. It’s a perfect way to spend a Saturday in Portland.

jake's crawfish seafood restaurant in POrtland Oregon

Day 3: Dinner – Jake’s Famous Crawfish

Enjoy a piece of Portland’s history at Jake’s Famous Crawfish in the downtown area. Jake’s has been serving fresh seafood for over 100 years and is quite the hot spot. I think I out-ordered hubby with my French onion soup and halibut fish and chips, paired with a glass of local Oregon wine. It’s in a cool area of town, so be sure to browse around after dinner and people-watch.

julian Kuhr plays for West Junction FC in Seattle

Day 3: Evening – Catch up on Portland Sports

Portland is a fantastic city if you love sports as they have plenty of teams to cheer for. You can catch a Trail Blazers basketball game, a Timbers soccer match, or a Thorns FC game, among others. We were here to watch the West Seattle Junction FC USL2 soccer game as they traveled down to play Portland PDX for a showdown. Of course, I might be biased since my favorite soccer player in the world plays for Seattle, so it gave us the perfect chance to be superfans.

Julian Kuhr plays for West Seattle Junction FC

If you have longer than 3 days in Portland, here are some other areas you might want to explore.

Top Day Trips from Portland

  1. Hood River (1 hour drive) – Hood River is a paradise for outdoor enthusiasts and you can enjoy activities like hiking, biking, windsurfing and visiting local orchards. The scenic drives in the Columbia River Gorge are amazing too.
  2. Nike Outlet Store (30-minute drive) – The Nike Outlet Store is a short drive away in Woodburn, and has a fantastic selection of Nike gear at discounted prices. Plus, the area has a variety of other outlets and restaurants so  it’s a great spot to spend a day shopping and exploring.
  3. Cannon Beach (1.5 hours drive) – This seaside town is filled with beautiful beaches, tide pools, and quaint shops and galleries. Be sure to check out Haystack Rock and enjoy the coastal scenery.
  4. Mount Hood (1.5 hours drive) – Oregon’s tallest mountain has outdoor activities year round. During the summer it’s perfect for  hiking and mountain biking, and  during the winter you can enjoy first- class skiing and snowboarding.
  5. Willamette Valley (1 hour drive) – The Willamette Valley is known for the pinot noir and has many wineries to visit with plenty of scenic countryside views. Tour the vineyards and taste some of Oregon’s best wines.

perfect itinerary for 3 days in Portland

Portland is a city that truly has it all, from its hip urban areas to its natural beauty. Whether you’re here 3 days in Portland or a longer stay, you’ll find plenty to do and see in this cool city.

If you’re looking to visit other cities in the area, you may enjoy the following articles:

48 hours in Vancouver – A perfect getaway from Seattle!

Top Things to See on Whidbey Island, the Perfect Day Trip from Seattle

The Lanzarotta Bed & Breakfast: Luxury Meets Nature in Oregon!

*** this article was sponsored but all opinions are my own ***

What would you do with 3 days in Portland?

Let me know in the comments below, and join me on Instagram and X!

About The Author

Samantha

I’m a travel and health writer, digital brand consultant, breast cancer survivor, and supermom to two boys! I keep it real and share stories of raising an active family, life after a cancer diagnosis, and family travels around the world! Each story is shared with my dry, and sometimes naughty sense of humor.

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