A weekend in Portland, Oregon: A 3-day itinerary

The following is a guest post by Anthony Presti.

Portland is a city of quirks and culture on the Columbia and Willamette rivers. Portland is known for its green outdoor spaces, colorful art scene, breweries, and independent eateries. After spending just a weekend in Portland, you’ll long to spend more. It’s a vibrant city with a lot to offer, from hiking in natural wonders to artsy shops and street food (food trucks aplenty!).

In this travel guide, I’ll take you through how to spend your time in the city and what activities you can’t miss. I’ll also give you some tips for planning your trip and how to make the most of your visit. Welcome to the Pacific Northwest!

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When to visit

Summer is the best time to visit, between the months of June and August. You’re more likely to get warm weather which is perfect for experiencing the outdoor activities the city has to offer. Although the summer months are busier with tourists, the rest of the year receives a fair amount of rain which may dampen your trip excursions. If you’re a fan of winter sports, you’ll find different activities such as skiing during the snow season from December to February.

A 3-Day Portland itinerary

There’s so much to see and do so where do you start? A few days over a long weekend in Portland is a great way to scratch the surface and see some of the most popular sights. Three days is the optimum amount of time to see a lot without being rushed, but there are plenty of things to do if you wish to extend your stay.

Day 1

Food

Food trucks in Portland are kind of a “thing”. The trucks are not mobile and stay in one location alongside their fellow “trucksters.” These collections of food trucks are nicknamed “pods” and they exist throughout the city. I suggest finding the nearest food truck pod to your accommodations and enjoying a unique taste of this great city before exploring.

Take a tour of food cart pods led by Lost Plate or Forktown, or take a bike tour of the pods with Around Portland Tours.

Walking Tour

After breakfast, start off your long weekend in Portland with a walking tour. This is a great way to get an overview of the city and find your bearings in an affordable way. There are a variety of different tours you can find depending on what you want to do. Look for one which will take you across the Broadway bridge and teach you some of the history of the city.

Coffee

A morning in Portland is not done right without a coffee, so head to Stumptown Coffee Roasters and grab yourself a latte. The coffee culture is a huge part of the city and you’ll see a range of independent coffee shops all over the city during your stay.

Voodoo Doughnut

You’ve just gotten your coffee, you know what’s missing? DOUGHNUTS! Voodoo Doughnuts is a must-visit for a fun and unique experience. The doughnut toppings are crazy, creative, and delicious. A perfect activity for the whole family to enjoy; don’t forget to bring your sweet tooth!

Take a doughnut tour on foot or by bike!

Old Town

Explore the old town where you’ll find a range of quirky and unique independent shops. You can also rent a bike to cycle around the streets and see more of the city, or take a bike tour.

Lan Su Chinese Garden

Take a moment to relax outside of the bustling streets of downtown Portland in the Lan Su Chinese Garden. As well as being a simply beautiful garden to walk around, it’s a small tranquil spot in the city with authentically built Chinese architecture. Wander around the garden and stop by the teahouse for an hour or so. It’s open daily between 10am and 6pm. Admission will cost $14 for adults and there’s wheelchair accessibility throughout the garden.

Powell’s City of Books

Book lovers will not want to miss Powell’s City of Books. One of the largest independent bookshops in the world, you could spend hours getting lost between the shelves. There are nine different rooms and approximately one million books – and it takes up an entire city block! Every type of book imaginable will be in Powell’s. It’s open daily from 10am-9pm. It is one of the best places in the city!

Deschutes Brewery

If you’d rather spend the afternoon drinking cold beers than reading books, head over to Deschutes Brewery. Great beer and great food are served here. Order one of their beer flights to sample the menu. There are a number of breweries across the city and if you’re there at the right time you might even experience one of the beer festivals.

Take a craft breweries walking tour or a Portland Brewery Bike Tour!

Chinatown

Conclude your first day in Portland with some food in Chinatown. There are plenty of choices to choose from but head to Chen’s Good Taste (18 NW 4th Ave.) if you want a classic Chinese dish. You can also visit one of the many bars in the area or head to a show at the Roseland Theatre.

Day 2

Portland Saturday Market

Begin your second day in Portland with a visit to the Saturday Farmers Market. In the summer months, it’s open every Saturday from 8:30am-2pm. Each week, the Tom McCall Waterfront Park is transformed by vendors selling local produce and arts. This is the perfect place to start your day and grab some breakfast while supporting local farmers and eateries. It’s one of the best things you can do while visiting a new city!

Portland Japanese Garden

Take the number 15 bus or the red or blue line light rail to the Portland Japanese Garden. This is much bigger than the Chinese garden from yesterday and a very different experience altogether. Allow yourself one and a half to two hours to walk around and experience its beauty. It’s known as the most authentic Japanese garden outside of Japan, so you won’t be disappointed. The gardens are open from Wednesday to Monday between 10am and 4:30pm. Admission will cost you $19.95 for an adult ticket. Although the entire gardens are not suitable for wheelchair users or strollers, there are some spaces that are, including the Flat Garden, Pavilion Gallery, and Cultural Village.

International Rose Test Garden

Discover why Portland is named the City of Roses at the International Rose Test Garden. Admission is free and it’s a two-minute walk from the Japanese Garden. You’ll see over 10,000 rose bushes and hundreds of different types of roses.

Blue Star Doughnuts

If you didn’t get enough doughnuts yesterday, head to Blue Star Doughnuts today. Although Voodoo doughnuts are a fun must-do experience, Blue Star doughnuts are actually hailed as the best-tasting doughnuts in the city.

Or try a doughnut tour on foot or by bike!

Pioneer Courthouse Square

Spend your afternoon in Portland at Pioneer Courthouse Square. This square has always got a lively event on, so check in advance what’s happening while you visit.

Eat Local

End your second day in Portland by visiting one of the many local restaurants. You’re truly spoiled for choice in this city, but if you want some recommendations, try Mucca Osteria for some amazing Italian goodness or Killer Burger for possibly one of the best burgers you’ll ever eat.

Alternatively, take a foodie tour of Portland’s “Restaurant Row” or a Downtown Portland Food Tour.

Day 3

For your final day in Portland, you’ll want to head outside of the city. Car rental will be essential for this day, unless you are taking your own to the city, or taking part in a tour.

Mount Hood

Drive two hours outside of Portland through the Columbia River Gorge to get to Mt. Hood, a mountain you’ve probably noticed while walking around the city; it’s the highest in the state. The drive is scenic and there’s plenty to do when you get there. Bring plenty of food and water, as well as suitable walking shoes if you decide to hike. Make sure to visit the Timberline Lodge, featured in The Shining. You can take part in a tour to learn more about the lodge; tours depart at 11am, 1pm and 2pm. The lodge is also ADA accessible. You’ll want to spend the best part of the day at Mt. Hood, especially if you want to hike.

Multnomah Falls

You absolutely must visit Multnomah Falls: this will most likely be the highlight of your trip. The waterfall is impressive at 630ft tall (192 meters) and is one of the area’s most popular sites. You should reserve your ticket in advance as it will likely be busy with other tourists. A ticket costs $2. You can park just outside and there’s a short walk to the viewing platform which is also suitable for wheelchair users.

There are lots of tours available to Mount Hood and Multnomah Falls, both half-day and full-day. You can even take an air tour!

Portland Mercado

After your day exploring the great outdoors, head back towards the city to Portland Mercado for some delicious Latin American street food. There are a number of different food carts, so get stuck in and try something new. It’s open Sunday-Thursday 11am-8pm and Friday-Saturday 11am-9pm.

What to do if you have more than a weekend in Portland

I’ve only scratched the surface with the main attractions in Portland, but there’s plenty more to do if you have the time. Here are a few of my recommendations:

• Pittock Mansion – Learn about the history of one of the city’s most influential families.
• Witch’s Castle – Explore the old ruins and hear stories from the past.
• Freakybuttrue Perculiarium – A unique and quirky museum and gift shop of all things peculiar.
• Cinema 21 – A fantastic independent movie theatre loved by locals.
• Portland Aerial Tram – A great way to get a different view of the city with some spectacular views.
• Oregon Museum of Science and Industry – A great museum for science lovers.
• Alberta Arts District – Lots of culture, restaurants, cafes, and shops to explore in this part of the city.
• Kennedy School – A hotel, outdoor restaurant, bar, movie theatre, and brewery.
• Washington Park, Forest Park, and Mill Ends Park – If you have more time to walk around luscious green gardens, try these. Or take this Urban Hiking Tour.
• Willamette Valley – The perfect place to visit for wine lovers. Several tours go there.
• Portland Art Museum – Add some culture with a trip to the largest art museum in Oregon. The Portland Art Museum features Native American art, Northwest art, modern and contemporary art and an outdoor public sculpture garden.
• Salt And Straw – All I’ll say is you’ve never had ice cream like this before. Go there!

Where to stay in Portland

Portland has a range of accommodation options for all visitors. Most of the top attractions are located in the Northwest and Pearl district so you’ll want to find a hotel near there or close by in Downtown or the Central Eastside. These are some hotels I’d recommend you check out for your trip.

Society Hotel

A clean hotel in a historical building that offers both private and dorm rooms for an affordable price. The rooftop terrace is a great place to unwind and see spectacular views of the city. This hotel is perfect for someone on a budget who wants to spend the majority of their weekend in Portland out exploring the city.
Where: Downtown. Budget: $. Stand-out amenities: Roof terrace, bar, and café. ADA rooms for accessibility. Dog-friendly private suites.

Book Society Hotel.

Hotel Rose

A bright and bold hotel with colorful interiors, this hotel is perfectly located in the heart of the city. It’s a funky and quirky boutique hotel that feels authentically Portland.
Where: Downtown. Budget: $$. Stand-out amenities: Pets allowed, bike rental available, gym, bar, and restaurant. Accessible rooms and suites.

Book Hotel Rose.

The Nines

If you’re looking for a luxury stay in Portland then look no further than The Nines. The hotel has nine stories (hence the name) and offers the whole package when it comes to luxury. The rooms are spacious and artistically decorated, and the rooftop bar on the 15th floor is a standout feature.
Where: Downtown. Budget: $$$. Stand-out amenities: Pet-friendly, library, gym, restaurant, bar, and rooftop terrace. Accessible rooms.

Book The Nines Hotel.

Jupiter Hotel

Jupiter hotel is a great choice if you want a fun and lively stay in Portland with its direct access to the Doug, a popular music venue and bar. The rooms are fun, creative, and affordable.
Where: Central Eastside. Budget: $$. Stand-out amenities: Bike rental, pet-friendly, access to Doug bar.

Book Jupiter Hotel.

Lolo Pass

With dorm and private rooms, Lolo Pass is an affordable hotel in the Central Eastside. A clean and comfortable stay with plenty of amenities to keep you entertained.
Where: Central Eastside. Budget: $. Stand-out amenities: Yoga classes, art gallery, patio, rooftop terrace, and bar.

Book Lolo Pass.

As well as hotels, there is a range of private rentals all over the city. This is a great option if you want more space or plan to stay longer than a few nights.

Getting around Portland

Although Portland is a large city, it’s easy to get around. You can walk around the city center where a lot of the main points of interest are or use the public transport systems. Walking is a great way to experience the heart of the city, especially with all the walkable bridges and public footpaths. There are cycle lanes almost everywhere so cycling is another great way to see the city and cover more ground. The extensive transport systems are very affordable and will get you anywhere you need to go in the city. If you want to visit some places outside of the city then you may need to consider hiring a car for that trip, however, you won’t need a car during your time in the center.

Light Rail

The Light Rail is the easiest way to travel from the airport into the city. The trains run every 15 minutes and will cost you $2.50 for the 40-minute journey. There are five lines that run through downtown Portland. Take the red line from the airport into the city to start your trip.

Streetcar

The Portland Streetcar has three lines which are great for getting around the city, from downtown to the Pearl District. You’ll pay $2 for a 2.5-hour ticket or $5 for a whole day of travelling. These tickets will also allow you to travel on the buses and light rail.

Bus

The city also has an extensive network of buses to get you where you need to go. Get a Hop card to top up bus fares for your visit.

There’s lots to do in Portland and you’re sure to have a fun time exploring the city and surrounding areas. Whether you want to spend your time in quirky independent shops, walking through the green spaces, or visiting one of the most impressive waterfalls in the area, there’s something for everyone to enjoy.

About the author

Anthony Presti is a travel and finance writer based in the United States. Most of his career has been spent in the animal welfare field, but he is also passionate about travel and helping people find ways to finance their adventures via ValueQuack, his travel & finance website. ValueQuack is (or was – it seems to have disappeared) an online resource for travellers to find creative solutions to better afford their adventures. Follow his site on Pinterest.