This post contains affiliate links. That means I may earn a small commission at no extra cost to you, if you buy through my site. I appreciate your support of my site.

When you hear “Portland” do you think of Oregon or Maine? While Portland, Oregon may have gotten its name from Portland, Maine after a penny toss, there is no other city like it!

This 3 day Portland Itinerary is for the city on the west coast that strives to keep things weird! “Portlandia”, “ the Rose City”, “Bridge City”, “Stumptown”… the list of nicknames goes on and on for Portland, Oregon.

Portland has many nicknames and just as many things that it is known for including the hipster vibe, green spaces, coffee, and bikers. My favorite thing about Portland is that it is one of the best food cities in the US. What makes the food scene so special are all the food cart pods. My full guide on the food cart pods in Portland will show you the best in the city. You can be sure this Portland itinerary includes many of these can’t miss food cart pods.

In addition to the best places to eat, this 3 day Portland itinerary will also help you decide where to stay, how to get around, and the top things to do in Portland.

3 Day Portland Itinerary

Is Portland Safe?

One of the first questions travelers ask before visiting a new place is, how safe is it? Portland really got put on the map, not in a good way, after the 2020 BLM protests. It has left many potential visitors wondering if Portland is worth a visit or not.

The 2020 protests primarily took place in the Old Town neighborhood, which also includes Chinatown. As a result the streets are full of boarded up businesses. Chinatown is in decline and includes very few of the bustling businesses as it did the past decades.

Portland in general has a very large homeless population. I learned from locals that even before 2020 that homelessness was a huge problem. The protests and Covid-19 made the situation even worse. I have seen the homelessness crisis around the country, but the number of people living on the streets and in tents around Portland was devastating.

Unlike many US cities you’ll find individuals living on the streets throughout the entire city, not only downtown. The highest concentration is found in the Old Town though.

Back to the original question, is Portland safe? Unfortunately in Portland it seems like “safe” and “unsettling” are used interchangeably. It is sad to see so many people struggling, be asked for money continuously, and witness some strange behavior. While those things can and do happen, I wouldn’t say Portland is unsafe. I would recommend avoiding Old Town at night and limiting your time there, but you don’t need to completely avoid it.

How to Get Around Portland

Portland’s transportation system makes it really easy to get around the city without a car. I have been taking public transportation around the US. Other than big cities like NYC, the US public transportation pales in comparison to abroad. That being said Portland has a pretty decent system. A lot of people use it so it is safe and reliable. You can reach everywhere in this Portland 3 day itinerary by public transportation.

The system consists mainly of buses, but also several MAX light rail lines. The best part is if you have a contactless card (the Chase Sapphire Reserve is a great one for travel), you can pay with your credit card. There is no need to worry about where or how to buy tickets. Simply tap your card when you enter the bus or at the MAX light rail stations.

The red MAX line goes directly from PDX airport to downtown. The Amtrak train station is located in Old Town. While the reviews for the area online will make you terrified, the bus and light rail stops are only a couple minutes walk from the train station doors. Unless you arrive in the middle of the night you really don’t need to waste your money on a taxi fare.

Where to Stay in Portland

You’ll want to avoid staying in Old Town, but the Pearl District to the west or downtown to the south are both good options. Both neighborhoods are centrally located to everything you want to see, do, and eat during your 3 days in Portland.

I loved my stay at Hotel Vance in downtown, just north of the University of Portland. It was convenient to many different bus and MAX lines. I could walk to several of the places included in this Portland itinerary.

As for the hotel, it was opened in 2021 so it is really new and modern. The rooms are very clean with extremely comfy beds! The black out shades and quiet temperature control system really helped for good nights of sleep as well.

Other hotels in the area with good reviews include: Kimpton River Place Hotel, The Hotel Zags, and The Heathman Hotel.

Search for the best hotel deals throughout Portland.

Booking.com

Portland Itinerary Day 1

Start your time in Portland by spending one day in the Old Town and the Pearl District. End the day across the river on N Mississippi Avenue. If your 3 days in Portland include a Saturday, adjust this Portland itinerary so this day takes place on Saturday.

Tom McCall Waterfront Park

If you are staying at Hotel Vance as I suggested it works perfectly to start your day by walking north in Tom McCall Waterfront Park along the Willamette River. Don’t miss Mill Ends Park across the street. Seriously if you aren’t paying attention you will miss it. Its claim to fame is being the smallest park in the world!

Portland Saturday Market

If you read the safety section above you may be wondering why the day begins in Old Town. I was in the neighborhood a few different times and there is a completely different feel on Saturdays thanks to the Portland Saturday Market.

Every Saturday from March – December 24th there is the largest continuously running weekly open-air arts and craft market in the US. Each week there are over 150 booths with different artists showcasing their handicrafts. All the goods are made and sold by local Pacific Northwest artists.

Another Activity Option: I love taking free tours in every city I visit. Unfortunately Portland no longer has a free tour. The Underground Donut Tour is a great way to start off your 3 days in Portland. Not only will you get to know the city with the help of a local guide, you’ll also try some of the best donut shops in Portland.

Lunch at the Portland Saturday Market

It wouldn’t be a Portland event without food carts. I tried Horn of Africa and really liked my veggie plate, but as usual there were a lot of other good options so enjoy lunch while watching the hustle and bustle of the market.

Another Lunch Option: If the Portland Saturday market isn’t going on you can go to the nearby 5th Avenue Food Cart Pod, Third Avenue Food Cart Pod, or the Cart Blocks.

Portland Chinatown Museum

Only a couple blocks north of the market you’ll encounter the current state of Old Town and Chinatown. It’s very sad to see the large homeless population downtown. As mentioned it helps to visit on Saturday when there are more people around.

While the Portland Chinatown Museum doesn’t feel like it is located in a great spot, it makes sense to be in the once thriving Chinatown. The main exhibit details the history of how the Chinese population began and grew in Portland. It concludes with a connection to the current situation of the neighborhood.

The museum was very informative and gives an important history to Portland’s Chinatown. It makes all the homeless tents and boarded up buildings even sadder.

If there is only the permanent exhibit the admission is $5 instead of $8.

Another Activity Option: The Japanese American Museum of Oregon is a couple blocks north of the Chinatown Museum. The museum focuses on Issei life in Portland’s Japantown.

Voodoo Doughnut

It would be a shame to spend 3 days in Portland and not experience the donut scene. Voodoo Doughnut is the most popular donut shop in Portland. The lines might make you think otherwise, but it’s not a tourist trap. It is popular for a reason! The candy, cereal, and sugar topped donuts are worth the wait.

Pearl District Shopping & Powell’s City of Books

Next head to the Pearl District for some shopping. The one store you don’t want to miss is Powell’s City of Books. It really does feel like a city inside of Powell’s. The store is four floors and takes up an entire city block. If you can’t find the book you are looking for here, I don’t know where you will find it. Bibliophiles will be able to spend a long time here!

N Mississippi Avenue

After you have perused books to your heart’s content, head to N Mississippi Avenue. The cool street is full of shops, restaurants, music venues, bars, and other quirky spots.

Prost!

Prost is a German restaurant with a food cart pod. There are a lot of good choices here. I had DesiPDX which serves Indian street food. Matt’s BBQ is another top pick. I didn’t try their BBQ truck, but did have their meats at their BBQ taco truck at Hinterland. The BBQ definitely lived up to all the hype it receives.

Portland Itinerary: Day 2

Today is the day to learn more about Portland through art and history. If possible visit the museums on a weekday as there are typically less people.

Portland Art Museum

The Portland Art Museum isn’t as big as some of the huge art museums around the country, but I do think it should be added to the list of the best US art museums.

There are two buildings of the museum that are connected underground. When I visited I automatically decided to start in the main building on the 4th floor and work my way down. An employee in the elevator let me know that starting at the top floor was the best way to see both buildings of the museum if you wanted to see everything.

Of course I am the type of person that wants to see everything, but I did run out of time to thoroughly look through the modern building. Luckily I was ok with my quick walk through that building as modern art is my least favorite. I enjoyed the European art and the paintings from Northwest artists in the main building much more.

The special exhibits were also really interesting. Many often focus on regional events and/or artists. The temporary BLM protest exhibit was very popular. The photographs really showed a sense of what it was like to be in Portland in 2020.

The museum is closed on Mondays and Tuesdays so plan accordingly.

Pioneer Courthouse Square

Take a break between museums for another food cart lunch. The food cart pod at Pioneer Square is smaller with about five food carts. Fried Egg I’m in Love is a delicious choice. Weekdays the lines can be longer with many business people in the area. Sometimes there are weekday lunch hour music performances.

Oregon Historical Society

I spent 4.5 hours at the Oregon Historical Society so I clearly enjoyed learning about the state’s history! The main exhibit focuses on the overall history of Oregon from the early days and Native Americans up until more recent years. As a child the Oregon Trail computer game was very popular. When I reached this section of the exhibit it was quite exciting to learn more about the real history that the fictional game I loved was based on.

The other permanent exhibit, history hub, provides hands-on activities that focus on diversity.

The remainder of the museum has several small temporary exhibits that tell a variety of stories related to Oregon’s history. I would like to visit again to see the “Main Streets: Wesley Andrews Photo Postcards” exhibit. Unlike today when it is so easy to have photographs of everything, the photographs from the early 20th century weren’t as readily shared.

Alberta Arts District

The Alberta Arts District is another fun neighborhood to include on your 3 day Portland itinerary. The artsy neighborhood is full of murals, boutique shops, and trendy bars and restaurants.

Dinner at EEM

When I visit different places I often have a goal in mind. In Portland it was to visit as many food cart pods and try as many donut shops as possible. I had to try at least one actual restaurant though.

Local blogger Kay from The Awkward Traveller suggested EEM, a Thai BBQ restaurant. It was awesome to meet up with Kay and enjoy a really delicious meal. I love Thai and I love BBQ, put them together and it is the perfect combination!

The only bad part of the meal was realizing it was my last night in Portland and I didn’t have time to try more of Kay’s restaurant recommendations. Based on how good EEM was I know her other suggestions like these Mexican restaurants, would be delicious as well.

Portland Itinerary: Day 3

If you are hoping to see the best of Portland in 3 days you’ll want to explore some of the city’s green spaces. Follow day three on the day with the best weather. If you prefer guided tours many of the following sights and activities are included in this half-day Portland city tour.

Pittock Mansion

Pittock Mansion is the former home of Henry and Georgiana Pittock. The Oregonian newspaper which is still running today was started by Henry Pittock.

The historic mansion that was built in 1912 is open for self-guided tours. I would have liked a guided tour, but the informative signs along the way clearly describe the house and the Pittock family. It was fun to take my time and really soak in all the information. I appreciated all the details provided about the family members’ lives and interests.

The basement of the mansion typically has an exhibit on display. The grounds around the mansion are quite nice with a few trails and viewpoints. The forests surrounding the mansion will make you feel that you are far from the city.

That also means it isn’t the easiest place to reach. To get to the mansion without a car you will need to walk up and down the steep hill. The number 20 bus stops on W Burnside Road. From the stop it is almost a 20 minute walk. It’s a nice walk, but be prepared for the climb up. Remember what goes up, must come down as well!

Another Activity Option: Known for being six times larger than Central Park in NYC, Forest Park is where Portlanders go to hike when they don’t want to go far. The urban forest has more than 80 miles of trails.

Northwest District Lunch

If you are traveling without a car you may want to bring a lunch. It will eat up your time quite a bit to leave the area and return. If you choose to do so the Northwest District is nearby. This trendy neighborhood is full of boutique shops and delicious restaurants.

Within the Northwest District you will find the Nob Hill Food Carts. Bing Mi cooks up jianbings, savory Chinese crepes. They make a perfect lunch.

Washington Park & Hoyt Arboretum

Pittock Mansion is up the hill on the northside of W Burnside Road. Washington Park is on the other side of the road.

Washington Park is a big park with several gardens and attractions. The park includes Hoyt Arboretum with several miles of trails. I walked 1.25 miles on the wildwood trail. Posted signs were helpful pointing the way, but distances did not seem to be accurate. At one point I walked about .25 miles, but there was no mileage change on the signs. Another time I walked a short distance, but the signs claimed I lost .1 miles!

Free restrooms are located around the park. The ones near MAX station are seasonal and only open through September. The Hoyt Arboretum restrooms in the visitor center courtyard are typically open 8am – 9pm.

Another Activity Option: The Oregon Zoo is located directly in the park. If you have some extra time in your Portland itinerary go see the lions, tigers, and bears, oh my!

Within the northeast corner of Washington Park you may start smelling something sweet. That would be thanks to the International Rose Test Garden! When coming from Pittock Mansion, the garden is a good place to start your visit in the park.

The free gardens are of course full of roses. Peak time to visit is between May – October. At the beginning of October the gardens were still in full bloom.

The restrooms are open after the visitor center closes. The visitor center was closed when the online hours indicated differently.

Another Activity Option: The Portland Japanese Gardens require an admission, but are known as a very peaceful and beautiful place.

Dinner at Cartopia

For dinner venture to East Portland to the food cart pod Cartopia. I was so excited to try Chicken and Guns, but they were cash only when I visited. I settled for Bottle Rocket. Luckily my burger and green beans didn’t feel like settling at all.

More Time in Portland?

If you have additional time you could either spread this Portland 3 day itinerary out or go on some day trips.

• Explore the Pacific Ocean along Oregon’s coastline on this 8.5 hour day tour.

• Visit one of the country’s most popular waterfalls on the Columbia Gorge Waterfall tour.

• On the Willamette Valley Wintery tour, enjoy the scenery and taste local wines .

3 Day Portland Itinerary: The Best of the Rose City

3 Day Portland Itinerary

Is Portland Safe?

How to Get Around Portland

Where to Stay in Portland