A modern and progressive city, Portland has grown beyond its former status as an industrial port. The city offers locals and travelers alike amazing green urban spaces, fantastic dining, stacks of live music and a strong sense of community. Oh, and you are just a short drive from some of the best scenery in the United States.
Thinking about traveling to Portland? Our three day Portland itinerary will have you experiencing the top attractions, best eats and outdoor adventures like a local!
The best Neighborhoods to Stay in Portland
As you’ll find out, Portland is cut in two by the mighty Willamette River. The east side of Portland is a heavily residential area offering the opportunity to base yourself out or an Airbnb or VRBO for your three-day trip.
However, the most happening part of Portland is on the west side of the river in the Old Town and Pearl Districts. Home to some of the city’s best attractions, parks and restaurants, you will have everything you need within walking distance.
North Portland offers great nightlife and a little less of a crowd compared to downtown and the Pearl District. For this reason, you won’t go wrong considering this option.
The Best Time of Year to Visit
Because of the nature surrounding Portland, there isn’t a bad time to go to Oregon’s most populous city. The soaring mountains outside of the city offer plenty of winter adventures from skiing to snow-shoeing.
However, the warmer months see Portland’s green spaces come to life. In the temperate spring months, the cherry blossoms bloom, adding another layer of beauty to the city’s renowned Japanese Garden.
The summer brings the roses and the parks pack with residents enjoying the sun and Portland’s many urban oases. The atmosphere and excitement reach its zenith and there’s no better example of that than at the Saturday Market.
With Portland blooming through spring and summer, you will also have envious fall foliage to discover.
Day One: Donuts, History, and Bridges
After your travels into Portland, you may be feeling a bit peckish. If my instincts serve me right, then you should begin your Portland adventures at the one and only Voodoo Donuts. At some point over the next three days, you should definitely try the local favorite, Blue Star. But Voodoo Donuts is such a memorable experience and the treats are delightful.
With the incredible selection of donuts, it’s hard to nail down your choice, but the friendly staff are always excited to show off their knowledge and they’ll have you noshing on the best donut of your life (until you visit Blue Star).
After you’re well fed and energized, cross the street heading north and find yourself in Portland’s Old Town, along with Chinatown. A mini city within a larger one, Chinatown has so much amazing history within its streets. Along with the typical food and shops, Portland’s Chinatown is also home to the historic Shanghai Tunnels.
As one of the top attractions in Portland, the Shanghai Tunnels, also known as the Old Portland Underground, are a series of tunnels connecting a collection of businesses.
The plan was to create a simple path between the early shops and restaurants in Portland with the docks on the Willamette River just a few blocks away. From the docks all the way to the various basements, merchandise would arrive in the hands of vendors without seeing an ounce of daylight.
But you know what they say about best laid plans. Organized crime caught wind and they would hide in the tunnels and wait for the opportune moment to not only steal the produce but kidnap the sailors against their will. The process went on to be known as ‘Shanghaiing’.
The best way to explore these events in Portland, which have blended with mythical tales over time, is to sign up for this walking tour.
Post tour, it is time to trade Portland’s historical tales for a different kind of story. Novels. Hundreds and thousands of novels. Meander your way through the Old Town until you find yourself in the nearby Pearl District, a beautiful part of Portland.
It’s here that you will find Powell’s City of Books, the biggest bookstore on earth. The building, appropriately, is huge, so you won’t miss it. Upon entry, be sure to pick up the decorated map so you can navigate the endless aisles and levels.
Such is the size of the store that you can even pick up a grocery-style basket as you peruse. Loved by locals and visitors alike, the store is a Portland jewel and it’s suggested that you take your time and allocate a solid two hours to exploring.
From the cafe on the bottom floor, serving heart warming flat whites, to the musty rare book room on the top level, you will need every one of those 120 minutes.
As you wander out of the bookstore, no doubt with a couple of novels (maybe even a first edition?), make a beeline for the Willamette River. This body of water slices Portland in half. You will notice a series of bridges going from one side to the other, reminiscent of New York City.
While none may be as famous as the Brooklyn Bridge, you should still step foot on Broadway Bridge. Near to Union Station, this historic steel bridge tells the tale of Portland’s heritage as an industrial city.
But the real reason you are here is to appreciate the beautiful skyline of Oregon’s biggest city. See the ensuing bridges and downtown before strolling along the waterfront on the Pearl District side of the river.
Your path splits between the rolling river, ships and bridges on one side and the modern highrises on the other. As the sun falls on Portland, this casual stroll lights up with local joggers, dog walkers and friendly residents, giving you a wonderful insight into every day Portland life.
Post dinner, freshen up and return to Old Town for some of the best nightlife in Portland. The city’s evening revelry can sometimes be hard to spot, but on the main streets of each district exists the full spectrum of night time fun, from clubs and bars to open mics and karaoke joints.
In Old Town you will have a whole host of dance clubs from the Barrel Room to Dirty Nightclub. While the inner gamer can come to life at the two-story arcade bar called Ground Kontrol.
Portland’s Mississippi Avenue is a fantastic alternative, especially if you are seeking live music. Head to Mississippi Studios to see who is playing when you’re in town.
Where to Eat on Day One in Portland
As you explore the Old Town and Pearl District, pop into Kasbah Moroccan for some of the best lunch dishes in Portland. Great bang for your buck and exceedingly tasty, sample the best of Morocco before continuing on your merry way.
If you are going out on Mississippi Street, head to Quaintrelle. The vegetable-heavy establishment is all about the cauliflower, radishes, beets and onions. Whether you go all in or add on a rib-eye, the healthy and colorful dinner will hit the spot.
Day Two: Waterfalls, Lakes, and Mountains
As you enjoy your breakfast to begin day two, save some room so you can enjoy the wares at the Portland Saturday Market. Held every weekend from March to Christmas Eve, the vibrant City Market presents over 150 vendors selling the freshest produce, sweet treats, arts and craft along with fantastic live entertainment. Having run annually since 1974, the market is the place to be on a weekend morning in Portland.
You will find the market beneath the Burnside Bridge in Portland’s Old Town. Wander the aisles, try some uniquely Portland eats and enjoy what is a homegrown experience.
With a burst of energy and a smile on your face after exploring the exciting market, it’s time to go on an adventure. As your only full day in Portland, this is your chance to explore the world-class scenery that is within the city’s backyard.
On day one, you will have noticed the soaring mountain in the background from any part of the city. That snow-capped, glaciated peak is the immense Mt Hood. The mountain has been inspiring outdoor adventures for decades and today you get to join in on the action.
But first, Multnomah Falls! Thanks to the power of social media, the falls have become famous across the United States. The waterfalls have two separate sections, the first and biggest featuring a massive 542 feet (165m) into a pool. That pool then overflows into a secondary waterfall, dropping another 70 feet (21m).
The scenery is awe-inspiring, surrounded by dense greenery and rock slabs. The white veil of water creates some amazing opportunities for photography and the iconic bridge that crosses above the pool of water adds a unique flavor to every photo.
Trail closures and alternate routes to see the popular waterfall have become common over the last few years due to forest fires. You can stay up to date with the hiking trails for Multnomah Falls here.
From the falls, continue on your road trip through the Oregon countryside by making your way to the stunning Trillium Lake. From the lake, you will have spectacular views of Mt Hood, along with a welcoming natural playground to experience.
Unsurprisingly, the best thing to do here is to get out on the water and capture the views from your own kayak or stand-up paddleboard. Don’t stress if you have either of those things, as you can pick up some rentals through Mt Hood Outfitters.
The lake comprises an enormous 63 acres to explore. If you consider yourself to be a bit of an angler, grab a rod and see if you can catch some fresh trout. For those that choose to stay on land, you can admire Mt Hood from the sun-soaked beaches or complete the two-mile Trillium Lake Loop Trail. Seek different views and enjoy the sprawling wetlands on this casual trek.
With some paddling and hiking complete, venture to stop three, the Timberline Lodge at Mt Hood. With snow-capped peaks year-round, Mt Hood is one of the best places for summer skiing anywhere in the world. Join in on the fun for skiing or snowboarding under the sun, or take the chairlift up to 7000 feet (2134m).
From the top of the chairlift you can experience the best view of the Mt Hood summit, around 4000 feet (1219m) above. You will also be able to see the Palmer Snowfield and the imposing Mt Jefferson. The ride takes thirty minutes each way to complete, and you can also choose to hike down the mountain.
Speaking of treks, Mt Hood has some fantastic short day hikes to explore the area around the Timberline Lodge. None better than 1.2 mile (1.9km) hike to Veda Lake.
Post adventures kick back at the Timberline Lodge for a treat, or even dinner, and soak up the unforgettable scenery.
Where to Eat on Day Two in Portland
As you adventure around the mountains and Lake Trillium, have lunch at Mt Hood Brewing Co. The brewpub serves up refreshing small-batch ales along with all your favorite pub grub and pizzas with an upscale twist.
If you are in Portland for dinner on night two, stop by Eem for some amazing Thai BBQ. The fusion of Thai and classic BBQ may not be a common thing, but it’s what makes the restaurant as unique as it is mouthwatering.
Day Three: Gardens and Haunted Ruins
After an action packed day two, begin your final day in Portland with a splash of Zen at the Japanese Garden. Often rated as one of the best in the United States, the attention to detail and overall aesthetics, at the very least, makes it the most beautiful spot in the city.
Witness wooden bridges over soft creaks and tea houses where you can pick up your own matcha tea as you roam. Later walk through the traditional Japanese rock garden with mesmerizing rock pillars.
Spend as long as you like roaming the gardens, which shine even brighter on a clear day. From certain spots you can see the summit of Mt Hood and for a second, you are whisked away to the scenic Japanese countryside.
If you are in Portland over the summer, then add the Rose Garden to your itinerary. Across from the Japanese Garden, the International Rose Test Garden, presents visitors with over 10,000 rose bushes and almost 700 different roses.
Because of this, Portland is known as the City of Roses and receives a variety of roses from around the world where they can explore the plants’ viability and characteristics. The science behind it all may not interest many, but the beautiful sight of all the flowers with have you exploring the 4.5 acres in earnest.
To finish your travels through Portland, explore two of the city’s most popular and interesting landmarks. Just north of the gardens is the Pittock Mansion. The important, historic building was home to the Pittocks, a prominent local family who helped transform the otherwise small town into an industrial port.
The beautiful piece of architecture is now home to a museum. You can wander through and explore the enormous drawing room, library, and music room. All furnishing remain original, including the home’s harp, grand piano and dazzling chandeliers.
Post exploring the historic mansion, journey to Forest Park, the biggest green space in Portland. With over 5000 acres and 80 miles (129km) to explore, you can enjoy some easy hiking or biking and it is also the perfect place for a picnic with beautiful city views.
However, Forest Park is also home to the Witch’s Castle. One of the best treks in the park, the Wildwood Trail, will take you to the castle’s ruins. On arrival, you will discover one of the more odd and surreal attractions in the city.
No witches ever called this place home, but the stone ruins were the place of a tragic story. The medieval European-style structure was sold from one man to another in the 1800s. The buyer then eloped with the seller’s daughter, who then murdered the buyer. Ever since, the crumbling home has been haunted.
To dust off the ghosts and toast to your three days in Portland, finish up at Away Days Brewing Co. One of the top breweries in Portland offers their take on German, Irish and Czech pints along with wines and CBD infused beverages.
Where to Eat
Begin day three in Portland, Oregon by dining out on the best brunch in town. Tusk opened in 2016 and has quickly become the go-to for locals who wish to treat themselves with a Mediterranean-infused breakfast. With sharp and fresh flavors and healthy eats, this will be the perfect start to your day.
Between Forest Park and Away Days Brewing Co is Love Belizean, with homemade Caribbean cuisine served in a simple establishment. From stews to curries and meat plates, the restaurant is one of the best lunch spots in Portland.
Over the course of three days, you can see the best of Portland, Oregon. With many sprawling parks and gardens, you could easily spend 72-hours walking and enjoying picnics under the trees. If you are seeking a relaxing vacation and a chance to slow things down, Portland is the place to be.
But with an interesting history, a thriving live music scene along with spectacular mountains and valleys just a quick trip away, there lies a lot to do for those that want an action-packed three days in Portland.