Portland has always been an intriguing city to me for its hipster vibe, incredible nature, delectable street food, and affinity for craft beer. This 4-day Portland itinerary hits every feature that makes this Pacific Northwest hub such a remarkable place to visit. Although that’s not enough time to see everything Portland has to offer, it covers many of the city’s top sights.

My itinerary starts in Portland City Center where you can explore its vibrant downtown and upscale Pearl District. Personally, I think this is the best area to start any Portland trip since the light-rail train has such an efficient connection straight from the airport. However, don’t spend all your time in central Portland, make sure to venture to the surrounding neighbourhoods and do some day trips from Portland. The Alberta Arts District is home to incredible artists, North Williams and Mississippi brims with creative eateries, and Buckman and Hosford-Abernethy hosts several famous breweries.

I couldn’t resist the chance to wander into the beautiful nature in and around Portland, so I dedicated two days of this itinerary to the outdoors. From rose gardens and forested trails to epic waterfalls, Portland will charm any nature enthusiast.

Overall, I thought this was a fantastic trip to Portland, and there are so many places I would recommend to future visitors. Portland is a city where you can have it all, and I hope you get the chance to extend your itinerary.

I’ve also added some bonus tips for you on what to expect, how to travel around Portland safely and the costs below this Portland itinerary so you have all the information you need to have a great trip.

Portland Itinerary – 4 Days

Day 1 – Downtown Portland & Pearl District

Day 2 – Discover Portland’s Nature

Day 3 – Explore Portland’s Art, Food, and Beer Scenes

Day 4 – Columbia River Gorge Day Trip

Top Tips | Getting Around | Costs

PORTLAND ITINERARY – 4 DAYS

Day 1 – Downtown Portland & Pearl District

Portland’s efficient light-rail train connection from the airport, you can reach downtown Portland in minutes. That makes the downtown area the perfect place to start day 1 of your Portland adventure. If you booked a hotel near City Center, try to check-in early and drop off your luggage so you can get out exploring straight away.

Get your first taste of Portland’s incredible food scene by having a meal at one of its food trucks. The Third Avenue and 5^th Avenue Food Cart Pods are two nearby food courts with tons of culinary offerings from around the world. After a quick meal, check out some of the top attractions residing in the downtown district. The pedestrian-friendly streets are easy to navigate, picturesque parks line the waterfront, and there’s a wide range of retailers to shop tax-free.

Pioneer Courthouse Square is considered the “living room” of Portland and an interesting place to witness the city’s quirky personality. Don’t be surprised to see flash mobs, food vendors, and exciting festivals at the plaza. Before skipping over to the Pearl District, visit the famous Voodoo Doughnut to taste one of their creative concoctions. The Portland Oregon White Stag Sign makes a beautiful photo op and strolling along the Willamette River provides striking views of Burnside and Steel Bridge.

A more sophisticated vibe takes over when you reach the Pearl District, one of Portland’s stylish enclaves. Business-savvy Portlanders flourish in this laid-back district, and it’s home to boutique shops, prestigious restaurants, and some of Oregon’s best advertising agencies. Bars and craft breweries packed around every street corner offer many options for happy hour specials to say cheers to your first day in Portland.

Day 2 – Discover Portland’s Nature

Lace-up your hiking shoes and find out why Portland is a nature lover’s playground. The 2nd day of your itinerary explores radiant gardens, gorgeous parks, and takes you to a few of Portland’s hiking trails.

Located inside Washington Park about two miles outside of downtown Portland, the International Rose Test Garden shows you why Portland is called the “City of Roses.” The extravagant garden features more than 600 rose varieties and reaches its peak bloom around June. There is no entrance fee and hiking trails around the gardens reveal beautiful city views from the hillside.

Just beyond the rose gardens, the Portland Japanese Garden enchants visitors with its lush foliage, koi pond, and cascading waterfall. Presenting the aesthetics of Japanese culture, the gardens are a peaceful escape from the urban sprawl.

Outside of the gardens, Washington Park features several other recreational activities to keep you busy. Meet animals at the Oregon Zoo, shoot bow & arrows at the Washington Park Archery Range, or gaze at redwood trees at the Hoyt Arboretum. With at least 10 trails winding through the park, there’s no better place in Portland to connect with nature.

Complete the day with a visit to the Pittock Mansion and tour the grounds of this marvellous century-old estate. The city of Portland acquired the lavish residence in the mid-1960s and converted it into a historic house museum open to the public. Before wandering the 46 rooms inside the manor, admire its French Renaissance and Victorian architecture and check out the incredible views overlooking Portland.

Day 3 – Explore Portland’s Art, Food, and Beer Scenes

Today is about discovering what makes Portland culture so unique and exploring other neighbourhoods around the city. Portland is noted for its eccentric personality but also boasts one of the country’s best food and craft beer scenes.

The first stop was the quirky Alberta Arts District, which rests in northeast Portland. Lined with art galleries and boasting an alternative vibe, Alberta is where you’ll find lots of thought-provoking artwork. Before you go art gallery hopping, stop by Pine State Biscuits for buttery homemade biscuits and southern-style cuisine.

While Alberta’s main drag boasts beautiful art every day of the week, the last Thursday of the month takes things to a whole other level. Dubbed the Last Thursday Art Walk, the monthly street fair welcomes local artists, musicians, and street performers for a fun-filled celebration of the arts.

Bring your appetite for the remainder of the day to delve into Portland’s mishmash of culinary delights. The North Williams and Mississippi thoroughfares attract foodies for its dynamic range of cuisines. From the Fijian dishes and Indian spices served at The Big Elephant Kitchen to delicious tacos found at Prost Marketplace, you’ll never go hungry strolling down North Williams or North Mississippi Avenues. If you’re craving something sweet, Blue Star Donuts and Ruby Jewel Ice Cream are on the same block of North Mississippi Avenue.

Southeast Portland is the final destination, and the hip twin districts of Buckman and Hosford-Abernethy are a treasure trove for beer lovers. More than a dozen breweries set up shop here, and Portlanders are spoiled with a tremendous variety of microbrews. Driven by independent brewers, a beer crawl lets you taste multiple world-renowned brews. Some of the notable breweries to check out include Hair of the Dog Brewing Company, Baerlic Brewing Company, and the Cascade Brewing Barrel House.

Day 4 – Columbia River Gorge Day Trip

For the last day of this Portland itinerary, take a day trip to the majestic Columbia River Gorge. One of the Pacific Northwest’s greatest natural wonders, the gorge stretches for about 80 miles along the Oregon-Washington border. There are nearly 100 waterfalls just on the Oregon side of the Columbia River Gorge, and an easy day trip Portland brings you up close to several of them.

The 620-foot Multnomah Falls is Oregon’s tallest and arguably prettiest cascade. It rests only 30 miles outside of Portland and is a must-see for anyone staying in the city for at least a few days. Before departing, you don’t want to miss the chance of seeing this treasure with your own eyes.

There are three primary options to reach Multnomah Falls and explore the surrounding area. You can either rent a vehicle, book a day tour, or ride public transit leaving from the Gateway Transit Center. If you decide to rent a car, you may want to pick it up the day before and leave EARLY the next morning. The parking lot is often full by mid-morning, and the area is often congested. Called the Columbia Gorge Express, the public bus from Gateway Transit Center is your cheapest option, but make sure to read the schedule before your trip.

Once you arrive, Multnomah Falls greets you from the parking area, and watching the two-tiered cascade tumble behind the Benson Bridge is a breathtaking sight. If you have time, I’d recommend hiking the scenic trails around Multnomah Falls to find the other cascades hiding within the gorge. The Multnomah-Wahkeena Loop stretches for around 5 miles and takes you to no less than six waterfalls.

A great way to end an incredible trip to Portland, especially for waterfall lovers!

Itinerary Duration

As you can see above, I’ve plotted this Portland itinerary for 4 days, but I know there are lots of other incredible places here to explore. You could easily stretch it out to a 6 or 7-day itinerary, do some road trip from Portland and explore some of the more unusual things to do in Portland.

TOP TIPS

Don’t Forget Your Hiking Shoes – Portland may be called the “Rose City,” but you could give it an alternative title as the “City of Hikes.” There are more than 150 miles of trails that weave through all parts of the city and celebrate its splendour. Many Portlanders are active individuals who live a health-conscious lifestyle and frequently hit the trails. Don’t miss out on Portland’s natural beauty and bring your best hiking shoes to get some exercise.  

Pack a Rain Jacket – The lush scenery in and around Portland didn’t happen by accident. Portland receives higher rainfall than the national average, but probably not as much as you think. While other cities do have more rain throughout the year, Portland has way more rainy days per year. Portland often has more than 150 rainy days, but its showers are rarely a downpour. The rain falls more like a mist, and locals throw on a rain jacket to cope with the weather. Don’t be afraid to go outside even if rain is detected in the forecast. Bring a reliable rain jacket to ward off the showers and continue your fun in Portland’s splendid outdoors. 

Drink Craft Beer – Portland burst onto the brewpub scene decades ago, and it continues to be a global leader for craft breweries. The city has more breweries than anywhere else on the planet, and that recognition alone draws beer connoisseurs from around the world. Don’t leave Portland without stopping by a few breweries to test your hops knowledge. Widmer Brothers Brewery is an icon that still ranks among America’s top breweries, and Cascade Brewing Barrel House made a splash with its sour beers. 

Don’t Skip Brunch – Portlanders love a delicious brunch, and there are countless spots to pull up a chair for an early afternoon meal. It’s hard to find another city in America with this much passion for brunch, and you’ll find menus featuring all types of cuisines. From Vietnamese spots to Cuban breakfast delights, brunch is a meal not to bed missed in Portland. 

Food Trucks Galore – To save money on food, you can’t go wrong with the food trucks in Portland. And don’t worry about eating unsanitary or undercooked street food, the trucks here are some of the best in the country. One way Portland does it differently is by organizing food trucks into pods instead of having them on the go. Regular customers always know where their favourite food trucks will be, and there are hundreds of others to sample. Whether you’re craving Indian, Thai, Mexican, Korean, or some other type of cuisine, you’re sure to find it and save a few bucks. 

Cook Your Meals – If you need to save even more money on your trip to Portland, pick up groceries, and whip up meals from your accommodation. Portland has incredible farmers’ markets in the middle of the city and its surrounding communities. The farm-to-table reputation here is well-deserved, and it helps to save funds for other exciting activities. 

Leave EARLY for Multnomah Falls – No trip to Portland is complete without visiting the most iconic attraction in the state of Oregon. With Multnomah Falls only 30 miles from downtown Portland, it’s a popular outing to include in your itinerary. That’s why I included this picturesque waterfall in this itinerary for you. If you decide to rent a car and drive to the falls, make sure you depart at the crack of dawn. It’s not uncommon for the parking lot to be full by 8 am-9 am, especially on weekends and during the summer. Alternatively, you can take a shuttle to Multnomah Falls from the Gateway Transit Center for a $10 round trip.  

Visit During the Weekend – The Portland Saturday Market is a sight to behold, and this enormous market only operates on the weekends from March until Christmas Eve. As the largest continuous outdoor arts & crafts market in the United States, it’s a fantastic place to pick up a souvenir. Find everything from exquisite art, jewellery, clothing, and handmade crafts. There are tons of food trucks whipping up delicious meals, and live music entertains the crowd. Although I didn’t include the Portland Saturday Market on this itinerary, consider swinging by the riverfront location by Burnside Bridge if you plan to visit on the weekend. 

Day Trips – For this itinerary, I only included one day trip to the Columbia River Gorge, but there are dozens of amazing places within 2-3 hours driving distance from Portland. Several charming towns dot the Oregon Coast, and Mount Hood overlooks untouched wilderness in the other direction. If you have time to add a few extra days to your Portland vacation, definitely rent a car and explore the natural wonders of Oregon. 

Shop for Outdoor Gear – If you follow my suggestion and venture into Oregon’s great outdoors, then Portland is the perfect city to shop for outdoor gear. Columbia Sportswear Headquarters are located in Portland, and it’s hard to find better prices for clothing, bags, and accessories elsewhere. The Columbia Factory Store is in the Sellwood-Moreland neighbourhood, and downtown Portland has a Columbia Sportswear. 

GETTING AROUND

Portland boasts a reliable public transportation system that makes it easy to get around without a car for a few days. Rides on buses, light rail, and streetcars are affordable and easy to navigate throughout the city. The moment your flight lands, you can reach Portland’s bustling downtown within 45 minutes.

Portland International Airport (PDX) – The state of Oregon’s largest airport, PDX is conveniently located 12 miles from downtown Portland. PDX offers direct flights to most major United States destinations and numerous international hubs. It’s often considered the best airport in the United States, having won accolades from prominent travel magazines. Travelers rank PDX among the top airports thanks to its easy connection to Portland, top-notch amenities, delicious food carts, and abundance of shops. The MAX light-rail train connection to downtown Portland costs $2.50 for adults and operates from 4:45 am to 11:50 pm.

TriMet – The TriMet is Portland’s public transport network that offers residents and visitors bus, light rail, and commuter rail service across the Portland metro area. 84 bus lines operate around the metro area and many lines directly connect to other forms of public transport. The MAX light-rail spans from Portland City Center to the airport and trains depart every 15 minutes. Passengers needing to reach nearby towns such as Beaverton, Tualatin, and Wilsonville use the WES Commuter Rail that operates on weekdays. Adult fares for the TriMet cost $2.50 per ride or a day pass can be purchased for $5.

Taxi/Uber – Taxis, Uber, and other rideshare programs are widely available in the Portland metro area. Radio cabs cost $3.50 for one rider, $1 for an extra rider, and are $2.60 per mile afterwards. Portland Taxi Cab, PDX Yellow Cab, and Broadway Cab are other notable taxi companies in the area. If you’re a Zipcar member, you have access to dozens of vehicles in downtown Portland.

Bike – Portland is an easy city to navigate by bike and there are plenty of rentals available. Many Portlanders are eco-friendly, promote a healthy lifestyle, and commute to work by bike. Rentals are available by the hour, day, and week, and there’s also a bike-sharing program when you only need one ride.

Rental Car – If your plan is to stay within Portland city limits, I wouldn’t recommend renting a car. However, Portland has tons of exciting day trips less than two hours away by car. You’ll have more flexibility to explore the beautiful areas outside of Portland with a car handy.

COSTS

Accommodation – While you have the option to keep it classy or stay at traditional hotels in Portland, it doesn’t fall under the city’s mantra. Portlanders live by the slogan “Keep Portland Weird,” and there are numerous quirky types of lodging for all budgets. Once an elementary school, the 3-star Kennedy School Hotel may take the prize for the most unique accommodation in Portland. From cosy cottages to haunted venues, Portland truly does keep it weird with their themed lodging. Prices typically range from $80-$120 per night but will vary by season.

For budget travelers, Portland has hostels in vibrant areas such as the Hawthorne District or Nob Hill. Dorm beds usually start at $25 per night, and most private rooms range from $60-$90.

Food – Portland’s food scene is among the best in the United States, and travelers of all budgets can find tempting culinary offerings here. If you feel like splurging, Portland has many world-class restaurants operated by prestigious chefs. Most restaurant meals should be less than $20, but Portland has fine dining establishments where meals are upwards of $30-$40 per person. On average, daily food costs in Portland are usually around $25-$35 but will vary based on your preferences.

What makes Portland’s food scene stand out against most cities are the pods of food carts around the city. It’s believed that more than 500 licensed food carts operate in Portland. Budget travelers needing to stay frugal with their expenses can rely on these street food hubs to provide tasty, nourishing meals for a quality price. In fact, Portland gains praise as one of the world’s best street food destinations for their creativity and reliance on local produce. Sticking with food carts and buying groceries will significantly reduce your daily food costs in Portland.

I hope you love your 4-day Portland itinerary as much as I did. Leave me a comment below if you have any top tips you’d add.

Written by Daniel G

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